5-芳基-1，3-环己二酮在合成杂环化合物中的应用
|
摘要
本论文包括两部分内容,第一部分以5-芳基-1,3-环己二酮和5,5-二甲基-1,3-环己二酮为合成子,与2-氨基苯甲腈或4,5-二甲氧基-2-氨基苯甲腈反应,合成国内外未见报道的三环化合物吖啶酮衍生物和五环化合物6,14-二氨基-7-取代-7H,8H-喹啉并[2,3-a]吖啶衍生物。同时我们对合成中间体烯胺的方法进行了改进,用水代替苯做溶剂,以无机酸做催化剂也合成得到了目标产物,且改进后的方法与原先用甲苯做溶剂的方法相比,具有操作简单,成本低,对环境友好等优点。通过改变投料比例,缩短反应步骤,用两步反应也可直接合成得到了6,14-二氨基-7-取代-7H,8H-喹啉并[2,3-a]吖啶衍生物。
第二部分以5-芳基-1,3-环己二酮为合成子,利用一锅煮、水做溶剂和少许的无机酸为催化剂的绿色合成方法,合成得到了一系列结构新颖的八氢喹啉二酮、氧杂蒽和苯并吡喃衍生物。这些方法具有成本低、收率高、操作简单、对环境友好等优点。
全文共合成新杂环类衍生物50个,所合成的化合物结构经IR、1H NMR、MS和元素分析予以证实。对三个化合物通过X-Ray单晶衍射进一步确定了化合物的空间结构。
The work in this paper can be separated in two parts, one was that The 6,14-diamino- 7-substituted-7,8-dihydroquinolino[2,3-a]acridine deriveatives of new form of pentacyclic system were synthesized by 5-aryl-1,3-cyclohexanediones or 5,5-dimethy-1, 3-cyclo- hexanedione with 2-amino-4,5-dimethoxy benzonitrile and 2-aminobenzonitrile. We also improved the synthetic method ofβ-enaminones, the target product were also synthesized by using water as solvent with a little acid as catalyst. This improved method compared with the original method of using toluene as solvent shows a simpe, low cost, environmentally friendly, etc. advantages. In addition, we also change the ratio of the reactant to use two-step synthesis of 6,14-diamino-7-substituted-7,8- dihydroquinolino[2,3-a]acridine derivatives.
The other was synthesis a series of new octahydroquinazolinediones、xanthenes and tetrahydrobenzopyran derivatives from 5-aryl-1,3-cyclohexanedione by first using water as solvent with a amount of acid. This green synthesis method provides several advantages such as environmental friendliness, low cost, simple workup procedure and so on.
Fifty new heterocyclic compounds were synthesized in this paper, and the structures of all the synthesized compounds were characterized by IR, 1H NMR, MS spectrum and elemental analysis.
We also trained three single crystal to characterize the space configuration by using X-Ray diffraction.
第二部分以5-芳基-1,3-环己二酮为合成子,利用一锅煮、水做溶剂和少许的无机酸为催化剂的绿色合成方法,合成得到了一系列结构新颖的八氢喹啉二酮、氧杂蒽和苯并吡喃衍生物。这些方法具有成本低、收率高、操作简单、对环境友好等优点。
全文共合成新杂环类衍生物50个,所合成的化合物结构经IR、1H NMR、MS和元素分析予以证实。对三个化合物通过X-Ray单晶衍射进一步确定了化合物的空间结构。
The work in this paper can be separated in two parts, one was that The 6,14-diamino- 7-substituted-7,8-dihydroquinolino[2,3-a]acridine deriveatives of new form of pentacyclic system were synthesized by 5-aryl-1,3-cyclohexanediones or 5,5-dimethy-1, 3-cyclo- hexanedione with 2-amino-4,5-dimethoxy benzonitrile and 2-aminobenzonitrile. We also improved the synthetic method ofβ-enaminones, the target product were also synthesized by using water as solvent with a little acid as catalyst. This improved method compared with the original method of using toluene as solvent shows a simpe, low cost, environmentally friendly, etc. advantages. In addition, we also change the ratio of the reactant to use two-step synthesis of 6,14-diamino-7-substituted-7,8- dihydroquinolino[2,3-a]acridine derivatives.
The other was synthesis a series of new octahydroquinazolinediones、xanthenes and tetrahydrobenzopyran derivatives from 5-aryl-1,3-cyclohexanedione by first using water as solvent with a amount of acid. This green synthesis method provides several advantages such as environmental friendliness, low cost, simple workup procedure and so on.
Fifty new heterocyclic compounds were synthesized in this paper, and the structures of all the synthesized compounds were characterized by IR, 1H NMR, MS spectrum and elemental analysis.
We also trained three single crystal to characterize the space configuration by using X-Ray diffraction.
引文
[1] Mayer, E. L.; Talley, F. B.; Woodward, C. F. Nicotine InsecticidesⅡSearch for Activators[J]. Plant Qmarantine. l946, 709, 16-23.
[2] Bobbitt, J. M.; Kulkarni, C. L.; Dutta, C. P.; Kofod, H.; Chiong, K. Synthesis of indoles and carbolines via aminoacetaldehyde acetals[J]. J. Org. Chem. 1978, 43, 3541-3549.
[3] Valnot, J. Y. Reaction of Activated Methylene Compounds withα-Aminoimines; A New Synthesis of Pyrroles[J]. Synthesis. 1978, 8, 590-605.
[4] Friary, R. J.; Gilligan, J. M.; Szajewski, R. P.; Falci, K. J.; Franck, R. W. Heterocyclic synthesis via the intramolecular acylation of enamines derived from amino acids[J]. J. Org. Chem. 1973, 38, 3487-3501.
[5] Blache, Y.; Sinibaldi-Troin, M. E.; Hichour, M.; Benezech, V.; Chavignon, O.; Gramain, J. C.; Teulade, J. C.; Chapat, J. P. Heterocyclic enaminones: Photochemical synthesis of 6,7,8,9-tetra- hydro-5H-pyrido[2,3-b]indol-9-ones[J]. Tetrahedron. 1999, 55, 1959-1967.
[6] Aoyagi, Y.; Mizusaki, T.; Ohta, A. Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines[J]. Tetrahedron Lett. 1996, 37, 9203-9209.
[7] Heravi, M. M.; Baghernejad, B.; Hossein, A.; Oskooie, R. H. A novel and facile synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1Hindole-4(5H)-ones via a one-pot multi-component reaction[J]. Tetrahedron Lett. 2008, 49, 6101-6103.
[8] LeTourneau, M. E.; Peet, N. P. Functionalized pyrazoles from indazol-4-ols[J]. J. Org. Chem. 1987, 52, 4384-4389.
[9] El-Bermawy, M. A.; Abdel, A.; El-Swah, M. A.; Kadry, A. M.; Al-Ashmawi, M. I. A new versatile route to the synthesis of novel pypazole derivatives via intramolecular Michael reaction[J]. Boll. Chim. Farm. 1996, 135, 580-589.
[10] Strakova, I.; Strakovs, A.; Petrova, M. 3-aryl- and 2,3-diaryl-4-oxo-4,5,6,7-tetrahydroindazoles reactions of aryl and tosylhydrazones of dimedone and 1,3-cyclohexanedione with some aromatic and heteroaromatic aldehydes[J]. Chem. Heterocycl. Compd. 2005, 41, 203-211.
[11] Lee, M.; Moritomo, H.; Kanematsu, K. Construction of three types of fused isoindoles via furan- -pyrrole ring exchange reaction[J]. Tetrahedron. 1996, 52, 8169-8174.
[12] Asouti, A.; Hadjiarapoglou, L. P. [3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclo- hexanemethylide: Facile synthesis of fused dihydrofuran derivatives[J]. Tetrahedron Lett. 1998, 39, 9073-9081.
[13] Paresh, D.; Salgaonkar, V.; Shukla, G.; Krishnacharya, G. A. A-Bromination of 1,3-Dicarbonyl Compounds Using Dess–Martin Periodinane (DMP) and Tetraethylammonium Bromide (TEAB)[J]. Synth. Commun. 2007, 37, 275-280.
[14] Arcadi, A.; Alfonsi, M.; Chiarini, M.; Marinelli, F. Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds[J]. J. Org. Chem. 2009, 694, 576-582.
[15] Tanaka, K.; Kishida, M.; Maeno, S.; Mitsuhashi, K. Reactions of Trifluoroacetonitrile Oxide or nitrilimines withβ-Diketones andβ-Keto Esters[J]. Bull. Chem. Soc. Jpn. 1986, 59, 2631-2644.
[16] L'abbe, G.; Buelens, J.; Dehaen, W.; Toppet, S.; Meervelt, L. Chlorine displacement of heterocyclic halides by enolate-oxygen: synthesis of 1,3-oxathiol-2-imines from 5-chloro-1,2,4-thiadiazol-3(2H)- ones and active methylene ketones and esters[J]. J. Chem. Soc. Perkin Trans. 1994, 1, 1263-1291.
[17] Kloc, K.; Mlochowski, J. Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes[J]. Tetrahedron Lett. 2001, 42, 4899-4907.
[18] Troschütz, R.; Lückel, A. Nitroketenaminale, 6. Mitt.: Synthese von 4-Aryl-1,4-dihydround 4-Aryl-4,5-dihydro-5-nitro-nicotins?uremethylestern[J]. Arch. Pharm. 1991, 324, 73-81.
[19] Shutske, G. M.; Bores, G. M.; Brandshaw, K. C.; Huger, F. P.; Kapples, K. J.; Larsen, R. D.; Rush, D. K.; Tommer, J. D. Synthesis and biological activity of putative mono-hydroxylated metabolites of velnacrine[J]. Bioorg. Med. Chem. Lett. 1992, 2, 865-871.
[20] Yadav, J. S.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R. Sulfamic acid: an efficient, cost-effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis[J]. Tetrahedron Lett. 2005, 46, 7249-7253.
[21] Chen, W. Y.; Lu, J.; Jin, J. R. Synthesis of Polyhydroquinoline Derivatives Under Solvent-Free Conditions[J]. Lett. Org. Chem. 2006, 3, 317-319.
[22] Gao, S. J.; Tsai, C. H.; Tseng, C.; Yao, C. F. Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media[J]. Tetrahedron. 2008, 64, 9143-9149.
[23] Singh, K.; Singh, J.; Singh, H. A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles[J]. Tetrahedron. 1996, 52, 14273-14281.
[24]史达清,庄启亚,陈景.水溶剂中芳醛与5,5-二甲基-1,3-环己二酮的反应[J].有机化学. 2003, 23(7), 684-696.
[25]靳通收,张建设,王爱卿,张伏生.水中3,3,6,6-四甲基-9-芳基-1,8-二氧-1,2,3,4,5,6,7,8-八氢化氧杂蒽的合成[J].有机化学. 2005, 25(3), 335-338.
[26]华国平,李团结,朱松磊,张晓镜.无催化剂条件下经微波辐射一步合成9-芳基-3,4,5,6,7,9-六氢-1H-氧杂蒽-1,8(2H)-二酮[J].有机化学. 2005, 25(6), 716-719.
[27]范学森,李艳贞,张新迎.离子液体介质中FeCl3·6H20催化下芳香醛与5,5-二甲基-1,3-环己二酮的缩合反应[J].有机化学. 2005, 25(11), 1482-1486.
[28] Hu, X. Y.; Fan, X. S.; Zhang, X. Y. A green and eficient synthesis of xanthenedione derivatives promoted by InCl3·4H20 in ionic liquid[J]. Chin. Chem. Lett. 2005, 16(3), 293-295.
[29]马晶军,李敬慈,唐然肖.离子液体中NaHSO4催化芳香醛与l,3-环己二酮的缩合反应[J].有机化学. 2007, 27(5), 640-642.
[30]唐然肖,何红岩,杨旭哲.微波辐射下酸性离子液体促进氧杂蒽二酮类衍生物的合成[J].化学试剂. 2007, 29(3), 173-174.
[31]王桂兰,曾必文,康晖,胡学超.酸性离子液体催化合成9-芳基-2,3,4,5,6,7-六氢-2H-氧杂葸-1,8-二酮[J].化学试剂. 2008, 30(10), 773-775.
[32]刘迪,于杨,张少华,刘春生,罗根祥.硫酸氢钠催化合成14-烷基(芳基)-14H-二苯并[a, j]氧杂蒽类化合物[J].合成化学. 2007, 15(4), 516-518.
[33]张英群,王春,马晶军,高月华,耿庆芬.可膨胀石墨催化合成3,3,6,6-四甲基-9-芳基-1,2,3,4,5,6,7,8-八氢化氧杂蒽-1,8-二酮[J].有机化学. 2007, 27(9), 1147-1149.
[34] Kandeel, Z.E.; Farag, A.M.; Shaaban, M.R.; Elnagdi, M.H. Studies with 1, 3-diketones: A convenient synthesis of some tetrahydro-4H-benzopyran and tetrahydroquinoline derivatives[J]. Heteroat. Chem. 1996, 7, 35-44.
[35] Rong, L. C.; Li, X. Y.; Wang, H. Y. Efficient Synthesis of Tetrahydrobenzo[b]pyrans under Solvent-Free Conditions at Room Temperature[J]. Synth. Commun. 2006, 36, 2363-2369.
[36] Jain, M. L.; Soni, R. P. A Facile Synthesis of 2,3-Dihydro-1H-phenothiazin-4(10H)-ones[J]. Synthesis. 1983, 11, 933-942.
[37] Dominguez, J. N.; Lopez, S.; Charris, J.; Iarruso, L.; Lobo, G.; Semenov, A.; Olson, J. E.; Rosenthal, P. J. Synthesis and Antimalarial Effects of Phenothiazine Inhibitors of a Plasmodium falciparum Cysteine Protease[J]. J. Med. Chem. 1997, 40, 2726-2732.
[38] El Swah, M.; El Bermawy, M. A.; Aal, E. A.; Kadry, A. M.; Al Ashmawi, M. I. In situ annelation of enaminones by reaction with methyleneiminium intermediates[J]. Boll. Chim. Farm. 1997, 136, 527-537.
[39] Sarac, S.; Yarim, M.; Ertan, M.; Erol, K.; Aktan, Y. 4-Aryl-5-oxo-1,2,3,4,5,6,7,8-octahydroquin- azoline-2-thione derivatives: synthesis, enantiomeric separation and in vitro screening as calcium antagonists[J]. Boll. Chim.Farm. 1997, 136, 657-668.
[40] Sarac, S.; Yarim, M.; Ertan, M.; Boydag, S.; Erol, K. Synthesis, chemical and pharmacological properties of some 4-aryl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-diones[J]. Pharmazie. 1998, 53, 91-102.
[41] Ghorab, M. M.; Abdel-Gawad, S. M.; El Gaby, M. S. A. Synthesis and evaluation of some newfluorinated hydroquinazoline derivatives as antifungal agents[J]. II Farmaco. 2000, 55, 249-261.
[42] Abdel-Gawad, S. M.; El Gaby, M. S. A.; Ghorab, M. M. Synthesis and antifungal activity of novel pyrano[2′,3′4,5]thiazolo[2,3-b]quinazolines, pyrido[2′,3′4,5]thiazolo[2,3-b] quinazolines and pyrazolo[2′,3′4,5]thiazolo[2,3-b]quinazolines[J]. II Farmaco. 2000, 55, 287-211.
[43] Safak, C.; Simsek, R.; Altas, Y.; Erol, K.; Boydag, S. One pot synthesis of some new substituted hexahydro 2H-1, 3-benzoxazine derivatives[J]. Boll. Chim. Farm. 1996, 135, 482.
[44] Miyano, S.; Abe, N. Synthesis of 3, 3-Dimethyl-2, 3, 4, 5, 10, 11-hexahydro-11-phenyl-1H -dibenzo [b, e] [1, 4] diazepin-1-one, a New Tricyclic System[J]. Chem. Pharm. Bull. 1972, 20, 1588-1597.
[45] Tonkikh, N. N.; Strakovs, A.; Petrova, M. V. 10-aryl-7,7-dimethyl-5,6,7,8,9,10-hexahydro-11H- -pyrido[3,2-b][1,4]benzodiazepin-9-ones[J]. Chem. Heterocyc. Compd. 2004, 40, 944-953.
[46] Breslow, R.; Rideout, D. C. Temperature and matrix effects on migratory aptitude and stereo- chemistry in 1,2-migration to a divalent carbon[J]. J. Am. Chem. Soc. 1980, 102, 7816-7823.
[47] Lubineau, A.; Auge, J.; Queneau, Y. Water-promoted organic reactions[J]. Synthesis. 1994, 5, 741-760.
[48] KellEr, E.; Feringa, B. L. Ytterbium triflate catalyzed Michael additions ofβ-ketoesters in water[J]. Tetrahedron Lett. 1996, 37, 1879-1882.
[49] Manabe, K.; Mori, Y.; Kobayashi, S. Effects of Lewis acid-surfactant-combined catalysts on Aldol and Diels-Alder reactions in water[J]. Tetrahedron. 1999, 55, 11203-11208.
[50] Lubineau, A.; Meyer, E. Water-promoted organic reactions.Aldol reaction of silyl enol ethers with carbonyl compounds under atmospheric pressure and neutral conditions[J]. Tetrahedron. 1988, 44, 6065-6070.
[51] Gajewski, J. J.; Brichford, N. L. Secondary deuterium kinetic isotope effects in the aqueous Claisen rearrangement:evidence against an ionic transition state[J]. J. Am. Chem. Soc. 1994, 116,3165-3166.
[52] Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media. John Wiley & Sons, Inc. 1997.
[53]Tanner, D. Chiral aziridines-their synthesis and use in stereoselective transformations[J]. Angrew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
[54] Mckenna, M. T.; Proctor, G. R.; Young, L. C. Novel tacrine analogues for potential use against Alzheimer’s disease: Potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors[J]. J. Med. Chem. 1997, 40, 3516-3523.
[55] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramyldipeptide with acridne/acridone derivatives[J]. J. Med. Chem. 2001, 44, 3606-3615.
[56] Charmantray, F. ; Duflos, A. ; Lhomme, J. Synthesis and study of 4-hydroxymethyl-3-alkyl- aminoacridines as models of a new class of DNA intercalating-alkylating agents[J]. J. Chem. Soc.Perkin. Trans. I. 2001, 29, 62-68.
[57] Krishnegowda, G.; Thimmaiah, P.; Hedge, R. Synthesis and chemical characterization of 2-methoxy-N10-substitude acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells[J]. Bioorg. Med. Chem. 2002, 10, 2367-2380.
[58] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridne/acridone derivatives[J]. J. Med. Chem. 2003, 46, 183-189.
[59] Sheng, R.; Liu, G. Q. A tetrahydroacridine derivative inhibits cerebral ischemia and protects rat cortical neurons against glutamate-induced cytotoxicity[J]. Acta. Pharmacol. Sin. 2003, 24(5), 390-393.
[60] Masataka, I.; Chihiro, I.; Wu, T. S. Cancer chemopreventive activity of acridone alkaloids on Epstein-Barr virus Activation and two-stage mouse skin carcino gennesis[J]. Cancer Lett. 2003, 193, 133-138.
[61] Hedge, R.; Thimmaiah, P.; Yerigeri, M. Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells[J]. Eur. J. Med. Chem. 2004, 39, 161-177.
[62] Gregory, M. S.; Frank, A. P.; Kevin, J. K. 9-Amino-1,2,3,4-tetrahydroacridin-1-dols: synthesis and evaluation as potential Alzheimer’s disease therapeutics[J]. J. Med. Chem. 1989, 32, 1805-1813.
[63] McKenna, M. T.; Proctor, G. R.; Young, L. C. Novel tacrine analogues for potential use against Alzheimer’s disease: potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors[J]. J. Med. Chem. 1997, 40(22), 3516-3523.
[64] Fujiwara, S. Preparation of N-[4-quinolinylbenzyl]benzimidazole Derivatives as Immunosuo- oressants[P].日本公开特许公报. 06340658, 1993.
[65] Denny, W. A. Acridine derivatives as chemotherapeutic agents[J]. Curr. Med. Chem. 2002, 9, 1655-1665.
[66] Richard, L.; Stephan, S.; Ulrich, M. Transformation of acridone synthase to chalcone synthase[J]. FEBS Lett. 2001, 58, 413-417.
[67] Dzierzbicka, K.; Gozdowska, M.; Sowiski, P. NMR Studies of the MDP Conjugates with Amino-Acridine/Acridone Derivatives[J]. Lett. Peptide Sci. 1995, 5(5), 409-412.
[68] Bridewell, D. J.; Graeme, J. F.; Bruce, C. B. Topoisomerase I/II selectivity among derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA)[J]. Anticancer Drug Des. 2001, 16(6), 317-324.
[69] Baguley, B. C.; Zhuang, L.; Elaine, M. Experimental solid tumour activity of N-[2-(dimethy- lamino)ethyl]-acridine-4-carboxamide[J]. Cancer Chem. Ph. 1995, 36(3), 244-248.
[70]刘宏本,曹道贤.抗白血病新药-安吖啶[J].新药与临床. 1991, 10(3), 245-247.
[71]陈耀全.一种新的DNA探针-2-(N-二茂铁酰氨丙氧基)-6-氯-9-氨基吖啶的合成与性质[J].化学学报. 1993, 51(3), 308-312.
[72] Naofumi, S. Acridinium compound having a plurality of luminescent groups and binding groups, and conjugate thereof[J]. Tetrahedron Lett. 1996, 37, 8519-8522.
[73] Gurrieri S.; Wells K. S.; Johnson L. D. Direct Visualization of Individual DNA Molecules by Fluorescence Microscopy: Characterization of the Factors Affecting Signal/Background and Optimization of Imaging Conditions Using YOYO[J]. Anal. Biochem. 1997, 149, 44-53.
[74]庄惠生,王琼娥,陈国南.化学发光免疫分析试剂吖啶酯的合成新路线[J].高等学校化学学报. 1998, 19(12), 1933-1936.
[75] Marie, P.; David, P.; Alexandre, B. molecular Recognition of DNA by synthetic ligrands[J]. J. Am. Chem. Soc. 2001, 123, 9283-9292.
[76]周运友,严正权,汪乐余.新型荧光试剂N-9-吖啶基氨基乙酸的合成及其光谱性质[J].应用化学. 2003, 20(12), 1176-1179.
[77]周运友,严正权,胡蕾.新型荧光试剂N-9-吖啶基氨基乙酸及其甲酯的合成[J].合成化学. 2004, 12(6), 583-586.
[78]庄惠生,王琼娥,陈国南. 6种不同取代基的双吖啶类探针的化学发光性质及其构效关系的研究[J].光谱学与光谱分析. 2004, 24(12), 1514-1517.
[79]张静,陈敬华,庄惠生.一种新型双吖啶核酸探针的合成及应用[J].合成化学. 2005, 13(6), 588 -590.
[80] Rmantray, F.; Demeunynck, M.; Carrez, D. 4-Hydroxymethyl-3-aminoacridine derivatives as a new family of anticancer agents[J]. J. Med. Chem. 2003, 46(6), 967-977.
[81] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridne/acridone derivatives[J]. J. Med. Chem. 2003, 46, 183-189.
[82] Osborn, H. M.; Sweeney, J. The asymmetric synthesis of aziridines[J]. Tetrahedron: Asymmetry. 1997, 8(11), 1693-1715.
[83]韩光范,王进军,姜贵吉. 6,7-亚甲二氧基-1(1H,2H)-吖啶酮衍生物的合成及镇痛作用[J].药学学报. 1992, 27(4), 256-260.
[84]王文兰,王春梅. 6,7-亚甲二氧基-9-甲基-1(2H,4H)-吖啶酮衍生物的合成[J].合成化学. 2004, 12(3), 297-299.
[85]王香善,史达清,张燕飞.三乙基苄基氯化铵(TEBA)催化下水中9-芳基多氢吖啶衍生物的合成[J].有机化学. 2004, 24(4), 430-432.
[86]屠树江,缪春宝,于晨侠.微波辐射下4-(4-羟基-3-甲氧基)苯基-3,3,6,6-四甲基-1,8-二氧代1,2,3,4,5,6,7,8,9,10-十氢吖啶的合成和晶体结构[J].结构化学. 2002, 21(3), 313-316.
[87]王香善,史达清,王苏惠.微波辐射下9-芳基-10-对甲苯基多氢吖啶衍生物的合成[J].有机化学. 2003, 23(11), 1291-1293.
[88]王香善,史达清,屠树江. 2,2,7,7-四甲基-5,6-二氧代-9-(2-氯苯基)-10-(4-甲基苯基)-9,10-二氢-2H-吖啶的合成和晶体结构[J].结构化学. 2004, 23(1), 91-94.
[89]戴立言,陈英奇.芳基氟喹诺酮抗菌剂的合成新方法[J].有机化学. 2003, 23(8), 836-840.
[90]汪敦佳,黄玲. N-吡啶取代喹诺酮衍生物的合成及抗菌活性[J].化学试剂. 2004, 26(l), 47-49.
[91] Oshiro,Y.; Sam, S. Novel anfiPsyehofic agents with dopamine autoreeePtor agonist properties: synthesis and pharmaeology of 7-[4-(4-phenyl, 1-iperazinyl)btitoxy]-3,4-dihydro-2(1H)-quinolinone derivatives[J]. J. Med. Chem. 1998, 41(5), 658-667.
[92] Harper, S.; Avolio, S. Potent inhibitors of subgenomic hepatitis C virus RNA replieation through optimization of indole-N-aeetamide allostoric ihhibitors of the viral NS5B Polymerase[J]. J. Med. Chem. 2005, 48, 4547-4557.
[93]朱玉洁.喹诺酮类抗菌药的历史和概况[J].国外医药抗生素分册. 1999, 20(5), 109-110.
[94]葛海霞,王礼深. 2(H)-喹啉酮类化合物的药理活性及构效关系[J].药学进展. 2005, 29(7), 309-316.
[95]黄东萍,刘少诚. 2(IH)喹啉酮类化合物的合成及其抗血小板聚集活性[J].中国药物化学杂志. 1997, 7(4), 235-239.
[96]冉崇昭,夏霖. 2-(H)-喹啉酮类化合物的合成及降压活性[J].中国药科大学学报. 2000, 31(4), 246-250.
[97] Yarim, M.; Sarac, S.; Ertan, M.; Kilic, F. S.; Erol, K. Synthesis, enantioseparation and pharma-cological activity of 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydro-quinazoline-2- thiones[J]. Arzneim.-Forsch. 2002, 52, 27-33.
[98] Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives[J]. Il Farmaco. 2003, 58, 17-26.
[99] Kidwai, M.; Saxena, S.; Khan, K. R. M.; Thukral, S. S. Synthesis of 4-aryl-7,7-dimethyl-1,2,3,4,5, 6,7,8-octahydroquinazoline-2-one/thione-5-one derivatives and evaluation as antibacterials[J]. Eur. J. Med. Chem. 2005, 40, 816-824.
[100] Hassani, Z.; Islami, R. M.; Kalantari, M. An efficient one-pot synthesis of Octahydroquinazolinone derivativesusing catalytic amount of H2SO4 in water[J]. Bioorg. Med. Chem. Lett. 2006, 16, 4479-4482.
[101] Shaabani, A.; Sarvary, A.; Rahmati, A.; Rezayan, A. H. Ionic Liquid/Silica Sulfuric Acid Promoted Fast Synthesis of a Biginelli-Like Scaffold Reaction[J]. Lett. Org. Chem. 2007, 4, 68-71.
[102] Nagarapu, L.; Kumari, D. M.; Kumari, N. V.; Kantevari, S. MCM-41 catalyzed rapid and efficientone-pot synthesis of polyhydroquinolines via the Hantzsch reaction under solvent -free condions[J]. Catal. Commun. 2007, 8, 1871-1875.
[103] Montandon, J. B.; Zijlstra, F. J; Wilson, J. H. P.; Grandjean, E. M.; Cicurel, L. In-vitro versus in-vivo activities of new 5-lipoxygenase inhibitors with antiinflammatory activity[J]. Int. J. Tissue React. 1989, 11, 107-114.
[104] Noungoune, T. D.; Ngouela, S.; Tsamo, E. Xanthones as therapeutic agents: chemistry and pharmacology[J]. Adv. Phytomedic. 2006, 2, 273-286.
[105] Matsumoto, K.; Akao, Y.; Ohguchi, K.; Ito, T.; Tanaka, T.; Iinuma, M; Nozawa, Y. Xanthones induce cell-cycle arrest and apoptosis in human colon cancer DLD-1 cells[J]. Bioorg. Med. Chem. 2005, 13, 6064-6072.
[106] Surasak, L.; Erik, N. T.; Thijs, R. H. M.; Kouwen, S. P. Rhodomyrtone: A new candidate as natural antibacterial drug from Rhodomyrtus tomentosa[J]. J. phymed. 2009, 01, 10-21.
[107] Nakatani, K.; Yamakuni, T.; Kondo, N.; Arakawa, T.; Oosawa, K.; Shimamura, S. gamma-Mangostin inhibits inhibitor-kappaB kinase activity and decreases lipopoly- saccharide-induced cyclooxygenase-2 gene expression in C6 rat glioma cells[J]. Mol. Pharmacol. 2004, 66, 667-680.
[108] Itoh, T.; Ohguchi, K.; Iinuma, M.; Nozawa, Y.; Akao, Y. Inhibitory effect of xanthones isolated from the pericarp of Garcinia mangostana L. on rat basophilic leukemia RBL-2H3 cell degranulation[J]. Bioorg. Med. Chem. 2008, 16, 4500-4513.
[109] Nakatani, K.; Nakahara, N.; Arakawa, T.; Yasuda, H.; Ohizumi, Y. Inhibition of cyclooxygenase and prostaglandin E2 synthesis byγ-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells[J]. Biochem. Pharmacol. 2002, 63, 737-748.
[110] Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H. Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases[J]. J. Phys.D: Appl. Phys. 2002, 35, 1473-1482.
[111] Hunter, R. C.; Beveridge, T. J. Application of a pH-sensitive fluoroprobe (C-SNARF-4) for pH microenvironment analysis in Pseudomonas aeruginosa biofilms[J]. Appl. Environ. Microibiol. 2005, 71, 2501-2514.
[112] Alizadeh, N.; Babaei, M.; Aghamo, M.; Rohani, Shohre. Electrosynthesis of dixanthylene photochromic dye, characterization and ab initio calculations[J]. Dyes and Pigments. 2008, 76, 596-605.
[113] Kuthan, J.; Sebek, P.; Bohm, S. Advances in heterocyclic chemistry[M]. New York: Academic Press Inc. 1995, 19-27.
[114] Dimmock, J. R.; Raghavan, S. K.; Bigam, G. E. Evaluation of mannich bases of 2-arylidene-1, 3-diketones versus murine P388 leukemia[J]. Eur. J. Med. Chem. 1988, 23(2), 1l1-117.
[115] Jha, A.; Beal, J. Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone[J]. Tetrabedron Lett. 2004, 45(49), 8999-9001.
[116] Kuo, C. W.; Fang, J. M. Synthesis of xanthenes, indanes, and tetrabydronaphthalenes via intramoleeular phenylcarbonyl coupling reactions[J]. Synth Commun. 2001, 31(6), 877-892.
[117] Jin, T. S; Zhang, J. S.; Wang, A. Q. Solid-state condensation reactions between aldehydes and 5, 5-dimethyl-1,3-cyclohexanedione by grinding at room temperature[J]. Synth. Commun. 2005, 35(17), 2339-2345.
[118] Owens, G. S.; Abuomer, M. M. Comparative kinetic investigations in ionic liquids using the MTO/peroxide system[J]. J. Mo1. Cata1. A: Chem. 2002, 187(2), 215-225.
[119] Das, B.; Thirupathi, P.; Mahender, I. An efficient reusable heterogeneous catalyst for the synthesis of 1, 8-dioxooctahydroxanthenes and 1, 8-dioxodecahydroacridines[J]. J. Mo1. Cata1. A: Chem. 2006, 247(12), 233-239.
[120]华国平,李团结,朱松磊.无催化剂条件下经微波辐射一步合成9-芳基-3,4,5,6,7,9-六氢-1H-氧杂蒽-1,8-(2H)-二酮[J].有机化学. 2005, 25(6), 716-719.
[121] Jin, T. S.; Zhang, J. S.; Wang, A. Q. U1-trasound-assisted synthesis of 1,8-diox- octahydroxanthene derivatives catalyzed by P-dodecylbenzene-sulfonie acid in aqueous media[J]. Ultrason. Sonochem. 2006, 13(3), 220-224.
[122] Isabelle, K.; Marc, H.; Stephane, C. 6-substituted-2-oxo-2H-1-benzopyran-3-carboxylic acid Derivatives in a new approach of the treatment of cancer cell invasion and metastasis[J]. Eur. J. Med. Chem. 2008, 43, 2735-2750.
[123] Siegfriend, E.; Drewes, F.; Fatima, K.; Alvaro, K. Simple 1,4-benzoquinones with anti- bacterial activity from stems and leaves of Gunnera Perpensa[J]. Eur. J. Med. Chem. 2005, 66, 1812-1816.
[124] Franco, C.; Bruna, B.; Adriana, B. Synthesis and in vitro selective ani-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamide[J]. Photosynth. Res. 2006, 41, 208-212.
[125] Zaizen, Y.; Hignchi Y.; Matsuo, N.; Shirahe, K.; Tokuda, H.; Takehita, M. Antitumor effects of soybean hypocotyls and soybeans on the mammary tumor induction by N-methyl-n-nitrosourean in F344 rats[J]. Anticancer Res. 2000, 20, 1439-1444.
[126] Zav’yalov, S.; Kondrat’eva, G.; Kudryavstseva, L. Nucleophilic reactions of dihydro- resorcinol and its derivatives in solvents with low polarity[J]. Zh. Obshchi. Khim. 1961, 31, 3695-3700.
[127] Kharchenko, V. G.; Markova, L. I.; Korshunova, K. M. On reactions of oxo-1,5-diketones with sulfurous reagents[J]. Zh. Orga. Khim. 1976, 12, 663-668.
[128] Eistert, B.; Schmitt, A.; Arackal, T. J. Reactions of 2,6-diphenyl(thio)pyrylium salt with 1,3- cycloalkanediones[J]. Chem. Ber. 1976, 109, 1549-1559.
[129] Bravo, P.; Ticozzi, C. Cxygen heterocycles by sulphur ylide annulation 3,4,5,6,7,8-hexahydro-3-hydroxy-2H-1-benzopyran-5-ones from 2-(2′-oxoalkyl)-1,3- cyclohexanediones and dimethylsulphoxonium methylide. Gazzetta Chimica Italianan[J]. 1979, 109, 169-173.
[130] Kharchenko, V. G.; Markova, L. I.; Smirnova, N. S. Synthesis and catalytic hyd- rogenation of 5-oxotetrahydro-4H-chromenes[J]. Zh. Org. Khim. 1982, 18, 2184-2189.
[131] Ahluwalia, V.; Kiran, S.; Arora, K. An efficient and simple one-pot synthesis of 2,7-diaryl- 7,7-dimethyl-5-oxo-5,6,7,8-tetranhydro-4H-1-benzopyrans[J]. Indian J. Chem. 1991, 30, 1095- 1097.
[132]王文兰,李洵,王艳茹. 2,4,7-三芳基-5-氧代-5,6,7,8-四氢苯并吡喃衍生物的合成[J].合成化学. 2000, 8, 264-267.
[133] Ahmed, M.; Ahmed, S. A; Romman, U. A convenien one pot synthesis of substituted and unsubstituted 2,4-diaryl-5-oxo-5,6,7,8-tetrahydro-2-chromens[J]. Indian J. Chem. 2002, 41, 1087-1090.
[134]高原,屠树江,周建峰.无外加催化剂条件下2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并-[b]-吡喃-3-羧酸乙酯的合成[J].合成化学. 2001, 21, 535-537.
[135]屠树江,冯友建,刘晓虹.微波辐射下2-氨基-7, 7-二甲基-3-乙氧羰基-4-(2-呋喃)基-5-氧代-4H-5,6,7,8-四氢苯并吡喃的合成和晶体结构[J].合成化学. 2002, 21, 96-98.
[136]王进军,韩光范,邬旭然.顺(反)-2,4,7-三芳基-5-氧代-5,6,7,8-四氢苯并吡喃衍生物的合成[J].有机化学. 2003, 23, 827-831.
[137]包志坚,纪顺俊,陆军.水相无催化剂合成四氢苯并吡喃衍生物[J].合成化学. 2007, 15, 630-633.
[138] Craig, S.; Stori, J.; Micheal, E. A novel conus snail polypeptide causes excitotoxicity by blocking desensitization of AMPA receptors[J]. Curr. Biol. 2009, 17, 1273-1279.
[2] Bobbitt, J. M.; Kulkarni, C. L.; Dutta, C. P.; Kofod, H.; Chiong, K. Synthesis of indoles and carbolines via aminoacetaldehyde acetals[J]. J. Org. Chem. 1978, 43, 3541-3549.
[3] Valnot, J. Y. Reaction of Activated Methylene Compounds withα-Aminoimines; A New Synthesis of Pyrroles[J]. Synthesis. 1978, 8, 590-605.
[4] Friary, R. J.; Gilligan, J. M.; Szajewski, R. P.; Falci, K. J.; Franck, R. W. Heterocyclic synthesis via the intramolecular acylation of enamines derived from amino acids[J]. J. Org. Chem. 1973, 38, 3487-3501.
[5] Blache, Y.; Sinibaldi-Troin, M. E.; Hichour, M.; Benezech, V.; Chavignon, O.; Gramain, J. C.; Teulade, J. C.; Chapat, J. P. Heterocyclic enaminones: Photochemical synthesis of 6,7,8,9-tetra- hydro-5H-pyrido[2,3-b]indol-9-ones[J]. Tetrahedron. 1999, 55, 1959-1967.
[6] Aoyagi, Y.; Mizusaki, T.; Ohta, A. Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines[J]. Tetrahedron Lett. 1996, 37, 9203-9209.
[7] Heravi, M. M.; Baghernejad, B.; Hossein, A.; Oskooie, R. H. A novel and facile synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1Hindole-4(5H)-ones via a one-pot multi-component reaction[J]. Tetrahedron Lett. 2008, 49, 6101-6103.
[8] LeTourneau, M. E.; Peet, N. P. Functionalized pyrazoles from indazol-4-ols[J]. J. Org. Chem. 1987, 52, 4384-4389.
[9] El-Bermawy, M. A.; Abdel, A.; El-Swah, M. A.; Kadry, A. M.; Al-Ashmawi, M. I. A new versatile route to the synthesis of novel pypazole derivatives via intramolecular Michael reaction[J]. Boll. Chim. Farm. 1996, 135, 580-589.
[10] Strakova, I.; Strakovs, A.; Petrova, M. 3-aryl- and 2,3-diaryl-4-oxo-4,5,6,7-tetrahydroindazoles reactions of aryl and tosylhydrazones of dimedone and 1,3-cyclohexanedione with some aromatic and heteroaromatic aldehydes[J]. Chem. Heterocycl. Compd. 2005, 41, 203-211.
[11] Lee, M.; Moritomo, H.; Kanematsu, K. Construction of three types of fused isoindoles via furan- -pyrrole ring exchange reaction[J]. Tetrahedron. 1996, 52, 8169-8174.
[12] Asouti, A.; Hadjiarapoglou, L. P. [3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclo- hexanemethylide: Facile synthesis of fused dihydrofuran derivatives[J]. Tetrahedron Lett. 1998, 39, 9073-9081.
[13] Paresh, D.; Salgaonkar, V.; Shukla, G.; Krishnacharya, G. A. A-Bromination of 1,3-Dicarbonyl Compounds Using Dess–Martin Periodinane (DMP) and Tetraethylammonium Bromide (TEAB)[J]. Synth. Commun. 2007, 37, 275-280.
[14] Arcadi, A.; Alfonsi, M.; Chiarini, M.; Marinelli, F. Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds[J]. J. Org. Chem. 2009, 694, 576-582.
[15] Tanaka, K.; Kishida, M.; Maeno, S.; Mitsuhashi, K. Reactions of Trifluoroacetonitrile Oxide or nitrilimines withβ-Diketones andβ-Keto Esters[J]. Bull. Chem. Soc. Jpn. 1986, 59, 2631-2644.
[16] L'abbe, G.; Buelens, J.; Dehaen, W.; Toppet, S.; Meervelt, L. Chlorine displacement of heterocyclic halides by enolate-oxygen: synthesis of 1,3-oxathiol-2-imines from 5-chloro-1,2,4-thiadiazol-3(2H)- ones and active methylene ketones and esters[J]. J. Chem. Soc. Perkin Trans. 1994, 1, 1263-1291.
[17] Kloc, K.; Mlochowski, J. Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes[J]. Tetrahedron Lett. 2001, 42, 4899-4907.
[18] Troschütz, R.; Lückel, A. Nitroketenaminale, 6. Mitt.: Synthese von 4-Aryl-1,4-dihydround 4-Aryl-4,5-dihydro-5-nitro-nicotins?uremethylestern[J]. Arch. Pharm. 1991, 324, 73-81.
[19] Shutske, G. M.; Bores, G. M.; Brandshaw, K. C.; Huger, F. P.; Kapples, K. J.; Larsen, R. D.; Rush, D. K.; Tommer, J. D. Synthesis and biological activity of putative mono-hydroxylated metabolites of velnacrine[J]. Bioorg. Med. Chem. Lett. 1992, 2, 865-871.
[20] Yadav, J. S.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R. Sulfamic acid: an efficient, cost-effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis[J]. Tetrahedron Lett. 2005, 46, 7249-7253.
[21] Chen, W. Y.; Lu, J.; Jin, J. R. Synthesis of Polyhydroquinoline Derivatives Under Solvent-Free Conditions[J]. Lett. Org. Chem. 2006, 3, 317-319.
[22] Gao, S. J.; Tsai, C. H.; Tseng, C.; Yao, C. F. Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media[J]. Tetrahedron. 2008, 64, 9143-9149.
[23] Singh, K.; Singh, J.; Singh, H. A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles[J]. Tetrahedron. 1996, 52, 14273-14281.
[24]史达清,庄启亚,陈景.水溶剂中芳醛与5,5-二甲基-1,3-环己二酮的反应[J].有机化学. 2003, 23(7), 684-696.
[25]靳通收,张建设,王爱卿,张伏生.水中3,3,6,6-四甲基-9-芳基-1,8-二氧-1,2,3,4,5,6,7,8-八氢化氧杂蒽的合成[J].有机化学. 2005, 25(3), 335-338.
[26]华国平,李团结,朱松磊,张晓镜.无催化剂条件下经微波辐射一步合成9-芳基-3,4,5,6,7,9-六氢-1H-氧杂蒽-1,8(2H)-二酮[J].有机化学. 2005, 25(6), 716-719.
[27]范学森,李艳贞,张新迎.离子液体介质中FeCl3·6H20催化下芳香醛与5,5-二甲基-1,3-环己二酮的缩合反应[J].有机化学. 2005, 25(11), 1482-1486.
[28] Hu, X. Y.; Fan, X. S.; Zhang, X. Y. A green and eficient synthesis of xanthenedione derivatives promoted by InCl3·4H20 in ionic liquid[J]. Chin. Chem. Lett. 2005, 16(3), 293-295.
[29]马晶军,李敬慈,唐然肖.离子液体中NaHSO4催化芳香醛与l,3-环己二酮的缩合反应[J].有机化学. 2007, 27(5), 640-642.
[30]唐然肖,何红岩,杨旭哲.微波辐射下酸性离子液体促进氧杂蒽二酮类衍生物的合成[J].化学试剂. 2007, 29(3), 173-174.
[31]王桂兰,曾必文,康晖,胡学超.酸性离子液体催化合成9-芳基-2,3,4,5,6,7-六氢-2H-氧杂葸-1,8-二酮[J].化学试剂. 2008, 30(10), 773-775.
[32]刘迪,于杨,张少华,刘春生,罗根祥.硫酸氢钠催化合成14-烷基(芳基)-14H-二苯并[a, j]氧杂蒽类化合物[J].合成化学. 2007, 15(4), 516-518.
[33]张英群,王春,马晶军,高月华,耿庆芬.可膨胀石墨催化合成3,3,6,6-四甲基-9-芳基-1,2,3,4,5,6,7,8-八氢化氧杂蒽-1,8-二酮[J].有机化学. 2007, 27(9), 1147-1149.
[34] Kandeel, Z.E.; Farag, A.M.; Shaaban, M.R.; Elnagdi, M.H. Studies with 1, 3-diketones: A convenient synthesis of some tetrahydro-4H-benzopyran and tetrahydroquinoline derivatives[J]. Heteroat. Chem. 1996, 7, 35-44.
[35] Rong, L. C.; Li, X. Y.; Wang, H. Y. Efficient Synthesis of Tetrahydrobenzo[b]pyrans under Solvent-Free Conditions at Room Temperature[J]. Synth. Commun. 2006, 36, 2363-2369.
[36] Jain, M. L.; Soni, R. P. A Facile Synthesis of 2,3-Dihydro-1H-phenothiazin-4(10H)-ones[J]. Synthesis. 1983, 11, 933-942.
[37] Dominguez, J. N.; Lopez, S.; Charris, J.; Iarruso, L.; Lobo, G.; Semenov, A.; Olson, J. E.; Rosenthal, P. J. Synthesis and Antimalarial Effects of Phenothiazine Inhibitors of a Plasmodium falciparum Cysteine Protease[J]. J. Med. Chem. 1997, 40, 2726-2732.
[38] El Swah, M.; El Bermawy, M. A.; Aal, E. A.; Kadry, A. M.; Al Ashmawi, M. I. In situ annelation of enaminones by reaction with methyleneiminium intermediates[J]. Boll. Chim. Farm. 1997, 136, 527-537.
[39] Sarac, S.; Yarim, M.; Ertan, M.; Erol, K.; Aktan, Y. 4-Aryl-5-oxo-1,2,3,4,5,6,7,8-octahydroquin- azoline-2-thione derivatives: synthesis, enantiomeric separation and in vitro screening as calcium antagonists[J]. Boll. Chim.Farm. 1997, 136, 657-668.
[40] Sarac, S.; Yarim, M.; Ertan, M.; Boydag, S.; Erol, K. Synthesis, chemical and pharmacological properties of some 4-aryl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-diones[J]. Pharmazie. 1998, 53, 91-102.
[41] Ghorab, M. M.; Abdel-Gawad, S. M.; El Gaby, M. S. A. Synthesis and evaluation of some newfluorinated hydroquinazoline derivatives as antifungal agents[J]. II Farmaco. 2000, 55, 249-261.
[42] Abdel-Gawad, S. M.; El Gaby, M. S. A.; Ghorab, M. M. Synthesis and antifungal activity of novel pyrano[2′,3′4,5]thiazolo[2,3-b]quinazolines, pyrido[2′,3′4,5]thiazolo[2,3-b] quinazolines and pyrazolo[2′,3′4,5]thiazolo[2,3-b]quinazolines[J]. II Farmaco. 2000, 55, 287-211.
[43] Safak, C.; Simsek, R.; Altas, Y.; Erol, K.; Boydag, S. One pot synthesis of some new substituted hexahydro 2H-1, 3-benzoxazine derivatives[J]. Boll. Chim. Farm. 1996, 135, 482.
[44] Miyano, S.; Abe, N. Synthesis of 3, 3-Dimethyl-2, 3, 4, 5, 10, 11-hexahydro-11-phenyl-1H -dibenzo [b, e] [1, 4] diazepin-1-one, a New Tricyclic System[J]. Chem. Pharm. Bull. 1972, 20, 1588-1597.
[45] Tonkikh, N. N.; Strakovs, A.; Petrova, M. V. 10-aryl-7,7-dimethyl-5,6,7,8,9,10-hexahydro-11H- -pyrido[3,2-b][1,4]benzodiazepin-9-ones[J]. Chem. Heterocyc. Compd. 2004, 40, 944-953.
[46] Breslow, R.; Rideout, D. C. Temperature and matrix effects on migratory aptitude and stereo- chemistry in 1,2-migration to a divalent carbon[J]. J. Am. Chem. Soc. 1980, 102, 7816-7823.
[47] Lubineau, A.; Auge, J.; Queneau, Y. Water-promoted organic reactions[J]. Synthesis. 1994, 5, 741-760.
[48] KellEr, E.; Feringa, B. L. Ytterbium triflate catalyzed Michael additions ofβ-ketoesters in water[J]. Tetrahedron Lett. 1996, 37, 1879-1882.
[49] Manabe, K.; Mori, Y.; Kobayashi, S. Effects of Lewis acid-surfactant-combined catalysts on Aldol and Diels-Alder reactions in water[J]. Tetrahedron. 1999, 55, 11203-11208.
[50] Lubineau, A.; Meyer, E. Water-promoted organic reactions.Aldol reaction of silyl enol ethers with carbonyl compounds under atmospheric pressure and neutral conditions[J]. Tetrahedron. 1988, 44, 6065-6070.
[51] Gajewski, J. J.; Brichford, N. L. Secondary deuterium kinetic isotope effects in the aqueous Claisen rearrangement:evidence against an ionic transition state[J]. J. Am. Chem. Soc. 1994, 116,3165-3166.
[52] Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media. John Wiley & Sons, Inc. 1997.
[53]Tanner, D. Chiral aziridines-their synthesis and use in stereoselective transformations[J]. Angrew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
[54] Mckenna, M. T.; Proctor, G. R.; Young, L. C. Novel tacrine analogues for potential use against Alzheimer’s disease: Potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors[J]. J. Med. Chem. 1997, 40, 3516-3523.
[55] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramyldipeptide with acridne/acridone derivatives[J]. J. Med. Chem. 2001, 44, 3606-3615.
[56] Charmantray, F. ; Duflos, A. ; Lhomme, J. Synthesis and study of 4-hydroxymethyl-3-alkyl- aminoacridines as models of a new class of DNA intercalating-alkylating agents[J]. J. Chem. Soc.Perkin. Trans. I. 2001, 29, 62-68.
[57] Krishnegowda, G.; Thimmaiah, P.; Hedge, R. Synthesis and chemical characterization of 2-methoxy-N10-substitude acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells[J]. Bioorg. Med. Chem. 2002, 10, 2367-2380.
[58] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridne/acridone derivatives[J]. J. Med. Chem. 2003, 46, 183-189.
[59] Sheng, R.; Liu, G. Q. A tetrahydroacridine derivative inhibits cerebral ischemia and protects rat cortical neurons against glutamate-induced cytotoxicity[J]. Acta. Pharmacol. Sin. 2003, 24(5), 390-393.
[60] Masataka, I.; Chihiro, I.; Wu, T. S. Cancer chemopreventive activity of acridone alkaloids on Epstein-Barr virus Activation and two-stage mouse skin carcino gennesis[J]. Cancer Lett. 2003, 193, 133-138.
[61] Hedge, R.; Thimmaiah, P.; Yerigeri, M. Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells[J]. Eur. J. Med. Chem. 2004, 39, 161-177.
[62] Gregory, M. S.; Frank, A. P.; Kevin, J. K. 9-Amino-1,2,3,4-tetrahydroacridin-1-dols: synthesis and evaluation as potential Alzheimer’s disease therapeutics[J]. J. Med. Chem. 1989, 32, 1805-1813.
[63] McKenna, M. T.; Proctor, G. R.; Young, L. C. Novel tacrine analogues for potential use against Alzheimer’s disease: potent and selective acetylcholinesterase inhibitors and 5-HT uptake inhibitors[J]. J. Med. Chem. 1997, 40(22), 3516-3523.
[64] Fujiwara, S. Preparation of N-[4-quinolinylbenzyl]benzimidazole Derivatives as Immunosuo- oressants[P].日本公开特许公报. 06340658, 1993.
[65] Denny, W. A. Acridine derivatives as chemotherapeutic agents[J]. Curr. Med. Chem. 2002, 9, 1655-1665.
[66] Richard, L.; Stephan, S.; Ulrich, M. Transformation of acridone synthase to chalcone synthase[J]. FEBS Lett. 2001, 58, 413-417.
[67] Dzierzbicka, K.; Gozdowska, M.; Sowiski, P. NMR Studies of the MDP Conjugates with Amino-Acridine/Acridone Derivatives[J]. Lett. Peptide Sci. 1995, 5(5), 409-412.
[68] Bridewell, D. J.; Graeme, J. F.; Bruce, C. B. Topoisomerase I/II selectivity among derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA)[J]. Anticancer Drug Des. 2001, 16(6), 317-324.
[69] Baguley, B. C.; Zhuang, L.; Elaine, M. Experimental solid tumour activity of N-[2-(dimethy- lamino)ethyl]-acridine-4-carboxamide[J]. Cancer Chem. Ph. 1995, 36(3), 244-248.
[70]刘宏本,曹道贤.抗白血病新药-安吖啶[J].新药与临床. 1991, 10(3), 245-247.
[71]陈耀全.一种新的DNA探针-2-(N-二茂铁酰氨丙氧基)-6-氯-9-氨基吖啶的合成与性质[J].化学学报. 1993, 51(3), 308-312.
[72] Naofumi, S. Acridinium compound having a plurality of luminescent groups and binding groups, and conjugate thereof[J]. Tetrahedron Lett. 1996, 37, 8519-8522.
[73] Gurrieri S.; Wells K. S.; Johnson L. D. Direct Visualization of Individual DNA Molecules by Fluorescence Microscopy: Characterization of the Factors Affecting Signal/Background and Optimization of Imaging Conditions Using YOYO[J]. Anal. Biochem. 1997, 149, 44-53.
[74]庄惠生,王琼娥,陈国南.化学发光免疫分析试剂吖啶酯的合成新路线[J].高等学校化学学报. 1998, 19(12), 1933-1936.
[75] Marie, P.; David, P.; Alexandre, B. molecular Recognition of DNA by synthetic ligrands[J]. J. Am. Chem. Soc. 2001, 123, 9283-9292.
[76]周运友,严正权,汪乐余.新型荧光试剂N-9-吖啶基氨基乙酸的合成及其光谱性质[J].应用化学. 2003, 20(12), 1176-1179.
[77]周运友,严正权,胡蕾.新型荧光试剂N-9-吖啶基氨基乙酸及其甲酯的合成[J].合成化学. 2004, 12(6), 583-586.
[78]庄惠生,王琼娥,陈国南. 6种不同取代基的双吖啶类探针的化学发光性质及其构效关系的研究[J].光谱学与光谱分析. 2004, 24(12), 1514-1517.
[79]张静,陈敬华,庄惠生.一种新型双吖啶核酸探针的合成及应用[J].合成化学. 2005, 13(6), 588 -590.
[80] Rmantray, F.; Demeunynck, M.; Carrez, D. 4-Hydroxymethyl-3-aminoacridine derivatives as a new family of anticancer agents[J]. J. Med. Chem. 2003, 46(6), 967-977.
[81] Dzierzbicka, K.; Kolodziejczyk, A. M. Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridne/acridone derivatives[J]. J. Med. Chem. 2003, 46, 183-189.
[82] Osborn, H. M.; Sweeney, J. The asymmetric synthesis of aziridines[J]. Tetrahedron: Asymmetry. 1997, 8(11), 1693-1715.
[83]韩光范,王进军,姜贵吉. 6,7-亚甲二氧基-1(1H,2H)-吖啶酮衍生物的合成及镇痛作用[J].药学学报. 1992, 27(4), 256-260.
[84]王文兰,王春梅. 6,7-亚甲二氧基-9-甲基-1(2H,4H)-吖啶酮衍生物的合成[J].合成化学. 2004, 12(3), 297-299.
[85]王香善,史达清,张燕飞.三乙基苄基氯化铵(TEBA)催化下水中9-芳基多氢吖啶衍生物的合成[J].有机化学. 2004, 24(4), 430-432.
[86]屠树江,缪春宝,于晨侠.微波辐射下4-(4-羟基-3-甲氧基)苯基-3,3,6,6-四甲基-1,8-二氧代1,2,3,4,5,6,7,8,9,10-十氢吖啶的合成和晶体结构[J].结构化学. 2002, 21(3), 313-316.
[87]王香善,史达清,王苏惠.微波辐射下9-芳基-10-对甲苯基多氢吖啶衍生物的合成[J].有机化学. 2003, 23(11), 1291-1293.
[88]王香善,史达清,屠树江. 2,2,7,7-四甲基-5,6-二氧代-9-(2-氯苯基)-10-(4-甲基苯基)-9,10-二氢-2H-吖啶的合成和晶体结构[J].结构化学. 2004, 23(1), 91-94.
[89]戴立言,陈英奇.芳基氟喹诺酮抗菌剂的合成新方法[J].有机化学. 2003, 23(8), 836-840.
[90]汪敦佳,黄玲. N-吡啶取代喹诺酮衍生物的合成及抗菌活性[J].化学试剂. 2004, 26(l), 47-49.
[91] Oshiro,Y.; Sam, S. Novel anfiPsyehofic agents with dopamine autoreeePtor agonist properties: synthesis and pharmaeology of 7-[4-(4-phenyl, 1-iperazinyl)btitoxy]-3,4-dihydro-2(1H)-quinolinone derivatives[J]. J. Med. Chem. 1998, 41(5), 658-667.
[92] Harper, S.; Avolio, S. Potent inhibitors of subgenomic hepatitis C virus RNA replieation through optimization of indole-N-aeetamide allostoric ihhibitors of the viral NS5B Polymerase[J]. J. Med. Chem. 2005, 48, 4547-4557.
[93]朱玉洁.喹诺酮类抗菌药的历史和概况[J].国外医药抗生素分册. 1999, 20(5), 109-110.
[94]葛海霞,王礼深. 2(H)-喹啉酮类化合物的药理活性及构效关系[J].药学进展. 2005, 29(7), 309-316.
[95]黄东萍,刘少诚. 2(IH)喹啉酮类化合物的合成及其抗血小板聚集活性[J].中国药物化学杂志. 1997, 7(4), 235-239.
[96]冉崇昭,夏霖. 2-(H)-喹啉酮类化合物的合成及降压活性[J].中国药科大学学报. 2000, 31(4), 246-250.
[97] Yarim, M.; Sarac, S.; Ertan, M.; Kilic, F. S.; Erol, K. Synthesis, enantioseparation and pharma-cological activity of 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydro-quinazoline-2- thiones[J]. Arzneim.-Forsch. 2002, 52, 27-33.
[98] Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives[J]. Il Farmaco. 2003, 58, 17-26.
[99] Kidwai, M.; Saxena, S.; Khan, K. R. M.; Thukral, S. S. Synthesis of 4-aryl-7,7-dimethyl-1,2,3,4,5, 6,7,8-octahydroquinazoline-2-one/thione-5-one derivatives and evaluation as antibacterials[J]. Eur. J. Med. Chem. 2005, 40, 816-824.
[100] Hassani, Z.; Islami, R. M.; Kalantari, M. An efficient one-pot synthesis of Octahydroquinazolinone derivativesusing catalytic amount of H2SO4 in water[J]. Bioorg. Med. Chem. Lett. 2006, 16, 4479-4482.
[101] Shaabani, A.; Sarvary, A.; Rahmati, A.; Rezayan, A. H. Ionic Liquid/Silica Sulfuric Acid Promoted Fast Synthesis of a Biginelli-Like Scaffold Reaction[J]. Lett. Org. Chem. 2007, 4, 68-71.
[102] Nagarapu, L.; Kumari, D. M.; Kumari, N. V.; Kantevari, S. MCM-41 catalyzed rapid and efficientone-pot synthesis of polyhydroquinolines via the Hantzsch reaction under solvent -free condions[J]. Catal. Commun. 2007, 8, 1871-1875.
[103] Montandon, J. B.; Zijlstra, F. J; Wilson, J. H. P.; Grandjean, E. M.; Cicurel, L. In-vitro versus in-vivo activities of new 5-lipoxygenase inhibitors with antiinflammatory activity[J]. Int. J. Tissue React. 1989, 11, 107-114.
[104] Noungoune, T. D.; Ngouela, S.; Tsamo, E. Xanthones as therapeutic agents: chemistry and pharmacology[J]. Adv. Phytomedic. 2006, 2, 273-286.
[105] Matsumoto, K.; Akao, Y.; Ohguchi, K.; Ito, T.; Tanaka, T.; Iinuma, M; Nozawa, Y. Xanthones induce cell-cycle arrest and apoptosis in human colon cancer DLD-1 cells[J]. Bioorg. Med. Chem. 2005, 13, 6064-6072.
[106] Surasak, L.; Erik, N. T.; Thijs, R. H. M.; Kouwen, S. P. Rhodomyrtone: A new candidate as natural antibacterial drug from Rhodomyrtus tomentosa[J]. J. phymed. 2009, 01, 10-21.
[107] Nakatani, K.; Yamakuni, T.; Kondo, N.; Arakawa, T.; Oosawa, K.; Shimamura, S. gamma-Mangostin inhibits inhibitor-kappaB kinase activity and decreases lipopoly- saccharide-induced cyclooxygenase-2 gene expression in C6 rat glioma cells[J]. Mol. Pharmacol. 2004, 66, 667-680.
[108] Itoh, T.; Ohguchi, K.; Iinuma, M.; Nozawa, Y.; Akao, Y. Inhibitory effect of xanthones isolated from the pericarp of Garcinia mangostana L. on rat basophilic leukemia RBL-2H3 cell degranulation[J]. Bioorg. Med. Chem. 2008, 16, 4500-4513.
[109] Nakatani, K.; Nakahara, N.; Arakawa, T.; Yasuda, H.; Ohizumi, Y. Inhibition of cyclooxygenase and prostaglandin E2 synthesis byγ-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells[J]. Biochem. Pharmacol. 2002, 63, 737-748.
[110] Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H. Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases[J]. J. Phys.D: Appl. Phys. 2002, 35, 1473-1482.
[111] Hunter, R. C.; Beveridge, T. J. Application of a pH-sensitive fluoroprobe (C-SNARF-4) for pH microenvironment analysis in Pseudomonas aeruginosa biofilms[J]. Appl. Environ. Microibiol. 2005, 71, 2501-2514.
[112] Alizadeh, N.; Babaei, M.; Aghamo, M.; Rohani, Shohre. Electrosynthesis of dixanthylene photochromic dye, characterization and ab initio calculations[J]. Dyes and Pigments. 2008, 76, 596-605.
[113] Kuthan, J.; Sebek, P.; Bohm, S. Advances in heterocyclic chemistry[M]. New York: Academic Press Inc. 1995, 19-27.
[114] Dimmock, J. R.; Raghavan, S. K.; Bigam, G. E. Evaluation of mannich bases of 2-arylidene-1, 3-diketones versus murine P388 leukemia[J]. Eur. J. Med. Chem. 1988, 23(2), 1l1-117.
[115] Jha, A.; Beal, J. Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone[J]. Tetrabedron Lett. 2004, 45(49), 8999-9001.
[116] Kuo, C. W.; Fang, J. M. Synthesis of xanthenes, indanes, and tetrabydronaphthalenes via intramoleeular phenylcarbonyl coupling reactions[J]. Synth Commun. 2001, 31(6), 877-892.
[117] Jin, T. S; Zhang, J. S.; Wang, A. Q. Solid-state condensation reactions between aldehydes and 5, 5-dimethyl-1,3-cyclohexanedione by grinding at room temperature[J]. Synth. Commun. 2005, 35(17), 2339-2345.
[118] Owens, G. S.; Abuomer, M. M. Comparative kinetic investigations in ionic liquids using the MTO/peroxide system[J]. J. Mo1. Cata1. A: Chem. 2002, 187(2), 215-225.
[119] Das, B.; Thirupathi, P.; Mahender, I. An efficient reusable heterogeneous catalyst for the synthesis of 1, 8-dioxooctahydroxanthenes and 1, 8-dioxodecahydroacridines[J]. J. Mo1. Cata1. A: Chem. 2006, 247(12), 233-239.
[120]华国平,李团结,朱松磊.无催化剂条件下经微波辐射一步合成9-芳基-3,4,5,6,7,9-六氢-1H-氧杂蒽-1,8-(2H)-二酮[J].有机化学. 2005, 25(6), 716-719.
[121] Jin, T. S.; Zhang, J. S.; Wang, A. Q. U1-trasound-assisted synthesis of 1,8-diox- octahydroxanthene derivatives catalyzed by P-dodecylbenzene-sulfonie acid in aqueous media[J]. Ultrason. Sonochem. 2006, 13(3), 220-224.
[122] Isabelle, K.; Marc, H.; Stephane, C. 6-substituted-2-oxo-2H-1-benzopyran-3-carboxylic acid Derivatives in a new approach of the treatment of cancer cell invasion and metastasis[J]. Eur. J. Med. Chem. 2008, 43, 2735-2750.
[123] Siegfriend, E.; Drewes, F.; Fatima, K.; Alvaro, K. Simple 1,4-benzoquinones with anti- bacterial activity from stems and leaves of Gunnera Perpensa[J]. Eur. J. Med. Chem. 2005, 66, 1812-1816.
[124] Franco, C.; Bruna, B.; Adriana, B. Synthesis and in vitro selective ani-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamide[J]. Photosynth. Res. 2006, 41, 208-212.
[125] Zaizen, Y.; Hignchi Y.; Matsuo, N.; Shirahe, K.; Tokuda, H.; Takehita, M. Antitumor effects of soybean hypocotyls and soybeans on the mammary tumor induction by N-methyl-n-nitrosourean in F344 rats[J]. Anticancer Res. 2000, 20, 1439-1444.
[126] Zav’yalov, S.; Kondrat’eva, G.; Kudryavstseva, L. Nucleophilic reactions of dihydro- resorcinol and its derivatives in solvents with low polarity[J]. Zh. Obshchi. Khim. 1961, 31, 3695-3700.
[127] Kharchenko, V. G.; Markova, L. I.; Korshunova, K. M. On reactions of oxo-1,5-diketones with sulfurous reagents[J]. Zh. Orga. Khim. 1976, 12, 663-668.
[128] Eistert, B.; Schmitt, A.; Arackal, T. J. Reactions of 2,6-diphenyl(thio)pyrylium salt with 1,3- cycloalkanediones[J]. Chem. Ber. 1976, 109, 1549-1559.
[129] Bravo, P.; Ticozzi, C. Cxygen heterocycles by sulphur ylide annulation 3,4,5,6,7,8-hexahydro-3-hydroxy-2H-1-benzopyran-5-ones from 2-(2′-oxoalkyl)-1,3- cyclohexanediones and dimethylsulphoxonium methylide. Gazzetta Chimica Italianan[J]. 1979, 109, 169-173.
[130] Kharchenko, V. G.; Markova, L. I.; Smirnova, N. S. Synthesis and catalytic hyd- rogenation of 5-oxotetrahydro-4H-chromenes[J]. Zh. Org. Khim. 1982, 18, 2184-2189.
[131] Ahluwalia, V.; Kiran, S.; Arora, K. An efficient and simple one-pot synthesis of 2,7-diaryl- 7,7-dimethyl-5-oxo-5,6,7,8-tetranhydro-4H-1-benzopyrans[J]. Indian J. Chem. 1991, 30, 1095- 1097.
[132]王文兰,李洵,王艳茹. 2,4,7-三芳基-5-氧代-5,6,7,8-四氢苯并吡喃衍生物的合成[J].合成化学. 2000, 8, 264-267.
[133] Ahmed, M.; Ahmed, S. A; Romman, U. A convenien one pot synthesis of substituted and unsubstituted 2,4-diaryl-5-oxo-5,6,7,8-tetrahydro-2-chromens[J]. Indian J. Chem. 2002, 41, 1087-1090.
[134]高原,屠树江,周建峰.无外加催化剂条件下2-氨基-3-氰基-4-芳基-7,7-二甲基-5-氧代-4H-5,6,7,8-四氢苯并-[b]-吡喃-3-羧酸乙酯的合成[J].合成化学. 2001, 21, 535-537.
[135]屠树江,冯友建,刘晓虹.微波辐射下2-氨基-7, 7-二甲基-3-乙氧羰基-4-(2-呋喃)基-5-氧代-4H-5,6,7,8-四氢苯并吡喃的合成和晶体结构[J].合成化学. 2002, 21, 96-98.
[136]王进军,韩光范,邬旭然.顺(反)-2,4,7-三芳基-5-氧代-5,6,7,8-四氢苯并吡喃衍生物的合成[J].有机化学. 2003, 23, 827-831.
[137]包志坚,纪顺俊,陆军.水相无催化剂合成四氢苯并吡喃衍生物[J].合成化学. 2007, 15, 630-633.
[138] Craig, S.; Stori, J.; Micheal, E. A novel conus snail polypeptide causes excitotoxicity by blocking desensitization of AMPA receptors[J]. Curr. Biol. 2009, 17, 1273-1279.