摘要
硝基咪唑是一类特殊结构的杂环,五元芳香杂环咪唑与硝基的共缀使其衍生物呈现广泛的应用潜力,在药物、人工诊断剂与人工探针等相关领域研究异常活跃,尤其是在医药方面作为人工合成的化学药物已在临床中广泛用于抗癌、抗菌、抗寄生虫等,备受关注.本文结合本课题组相关研究,参考国内外近期文献,系统地综述了硝基咪唑类化合物在药物化学领域的研究与应用,包括抗肿瘤、抗细菌、抗真菌、抗寄生虫、抗结核、抗高血压以及作为人工诊断剂与病理探针、超分子基体等领域的当前现状,展望了其未来可能的发展趋势.希望该评述能为硝基咪唑类杂环化合物的多用途开发提供有益的指导.
Nitroimidazoles are a class of structurally special heterocycles. The combination of five-membered aromatic heterocyclic imidazole and nitro group makes their derivatives to possess a wide variety of potential applications, and relevant researches of nitroimidazoles as drugs, artificial diagnostics, pathological probes and so on are quite active. In particular, nitroimidazoles as artificially synthetic chemical drugs have been widely used in the clinic for anticancers,antimicrobials, antiparasites etc.. Combining with our work and literatures in recent years, this work systematically reviewed the current researches and applications of nitroimidazole compounds in medicinal chemistry including antitumor, antibacterial, antifungal, antiparasitic, antitubercular, antihypertensive drugs as well as artificial diagnostics and pathological probes, supramolecular blocks. The foreseeable development trends were also prospected. This comprehensive review may provide a beneficial guide in the development of nitroimidazole heterocyclic compounds for multipurpose applications.
引文
1 Zhang L,Peng XM,Damu GLV,Geng RX,Zhou CH.Med Res Rev,2014,34:340-437
2 Repenko T,Rix A,Ludwanowski S,Go D,Kiessling F,Lederle W,Kuehne AJC.Nat Commun,2017,8:470
3 Iaroshenko VO,Gevorgyan A,Mkrtchyan S,Arakelyan K,Grigoryan T,Yedoyan J,Villinger A,Langer P.J Org Chem,2015,80:2103-2119
4 Roy MMD,Rivard E.Acc Chem Res,2017,50:2017-2025
5 Zhang HZ,Gan LL,Wang H,Zhou CH.Mini-Rev Med Chem,2017,17:122-166
6 Azam A,Peerzada MN,Ahmad K.Front Microbiol,2015,6:1183
7 Leitsch D,Kolarich D,Binder M,Stadlmann J,Altmann F,Duchêne M.Mol Microbiol,2009,72:518-536
8 Sackton KL,Dimova N,Zeng X,Tian W,Zhang M,Sackton TB,Meaders J,Pfaff KL,Sigoillot F,Yu H,Luo X,King RW.Nature,2014,514:646-649
9 Edgar LJ,Vellanki RN,Halupa A,Hedley D,Wouters BG,Nitz M.Angew Chem Int Ed,2014,53:11473-11477
10 Dey C,Banerjee R.Chem Commun,2013,49:6617-6619
11 Ang CW,Jarrad AM,Cooper MA,Blaskovich MAT.J Med Chem,2017,60:7636-7657
12 Mitchell MJ,Jain RK,Langer R.Nat Rev Cancer,2017,17:659-675
13 Pesonen S,Kangasniemi L,Hemminki A.Mol Pharm,2011,8:12-28
14 Firuzi O,Javidnia K,Mansourabadi E,Saso L,Mehdipour AR,Miri R.Arch Pharm Res,2013,36:1392-1402
15 Zhou C.General Medicinal Chemistry.Beijing:Science Press,2014(in Chinese)[周成合.基础药物化学.北京:科学出版社,2014]
16 Madeo F,Eisenberg T,Pietrocola F,Kroemer G.Science,2018,359:eaan2788
17 Bonnet M,Hong CR,Wong WW,Liew LP,Shome A,Wang J,Gu Y,Stevenson RJ,Qi W,Anderson RF,Pruijn FB,Wilson WR,Jamieson SMF,Hicks KO,Hay MP.J Med Chem,2018,61:1241-1254
18 Cai Y,Chen Z,Zhao F,Chen J.Chin J New Drugs,2003,12:249-253(in Chinese)[蔡芸,陈志龙,赵芳,陈静.中国新药杂志,2003,12:249-253]
19 Cai J,Li S,Zhou C,Gan L,Wu J.Chin J New Drugs,2009,18:598-608(in Chinese)[蔡佳利,李硕,周成合,甘淋玲,吴俊.中国新药杂志,2009,18:598-608]
20 Tanabe K,Kojima R,Hatta H,Nishimoto S.Bioorg Med Chem Lett,2004,14:2633-2635
21 Jin CZ,Nagasawa H,Shimamura M,Uto Y,Inayama S,Takeuchi Y,Kirk KL,Hori H.Bioorg Med Chem,2004,12:4917-4927
22 Li X,Liang J,Guan Z,Xu Z,Peng J.Pract J Cancer,2013,28:114-117](in Chinese)[李响,梁健刚,关中,徐志坚,彭解人.实用癌症杂志,2013,28:114-117]
23 Bonnet M,Hong CR,Gu Y,Anderson RF,Wilson WR,Pruijn FB,Wang J,Hicks KO,Hay MP.Bioorg Med Chem,2014,22:2123-2132
24 Zhuang Y,Zhou C,Wang Y,Li D.Chin Pharm J,2008,43:1281-1287(in Chinese)[庄雅云,周成合,王渝芳,李东红.中国药学杂志,2008,43:1281-1287]
25 Tang Y,Zhang J,Zhang S,Geng R,Zhou C.Chin J Chem,2012,30:1831-1840
26 Valderrama-Negrón AC,Alves WA,CruzáS,Rogero SO,de Oliveira Silva D.Inorg Chim Acta,2011,367:85-92
27 Yu K,Liu J,Zhou C,Diao J,Xu T,Li D.Chin J Med Chem,2008,18:414-419(in Chinese)[于克贵,刘建仓,周成合,刁俊林,胥婷,李东红.中国药物化学杂志,2008,18:414-419]
28 Lee RJ,Marais R.Nature,2017,550:192-193
29 Wei H,Li D,Yang X,Shang H,Fan S,Li Y,Song D.Molecules,2016,21:1693
30 Cheng W,Zhu S,Ma X,Qiu N,Peng P,Sheng R,Hu Y.Eur J Med Chem,2015,89:826-834
31 Gong HH,Baathulaa K,Lv JS,Cai GX,Zhou CH.Med Chem Commun,2016,7:924-931
32 Makawana JA,Sangani CB,Lin L,Zhu HL.Bioorg Med Chem Lett,2014,24:1734-1736
33 Makawana JA,Sun J,Zhu HL.Bioorg Med Chem Lett,2013,23:6264-6268
34 Luo Y,Li Y,Qiu KM,Lu X,Fu J,Zhu HL.Bioorg Med Chem,2011,19:6069-6076
35 Yan Z,Liu A,Huang M,Liu M,Pei H,Huang L,Yi H,Liu W,Hu A.Eur J Med Chem,2018,149:170-181
36 Tao XX,Duan YT,Chen LW,Tang DJ,Yang MR,Wang PF,Xu C,Zhu HL.Bioorg Med Chem Lett,2016,26:677-683
37 Karnthaler-Benbakka C,Groza D,Koblmüller B,Terenzi A,Holste K,Haider M,Baier D,Berger W,Heffeter P,Kowol CR,Keppler BK.ChemMedChem,2016,11:2410-2421
38 Liapis V,Zinonos I,Labrinidis A,Hay S,Ponomarev V,Panagopoulos V,Zysk A,DeNichilo M,Ingman W,Atkins GJ,Findlay DM,Zannettino ACW,Evdokiou A.Cancer Med,2016,5:534-545
39 Duan JX,Jiao H,Kaizerman J,Stanton T,Evans JW,Lan L,Lorente G,Banica M,Jung D,Wang J,Ma H,Li X,Yang Z,Hoffman RM,Ammons WS,Hart CP,Matteucci M.J Med Chem,2008,51:2412-2420
40 Harvey AL.Drug Discov Today,2008,13:894-901
41 Jin C,Wen S,Zhang Q,Zhu Q,Yu J,Lu W.ACS Med Chem Lett,2017,8:762-765
42 Ikeda Y,Hisano H,Nishikawa Y,Nagasaki Y.Mol Pharm,2016,13:2283-2289
43 Shang H,Chen H,Zhao D,Tang X,Liu Y,Pan L,Cheng M.Arch Pharm Pharm Med Chem,2012,345:43-48
44 Rami M,Dubois L,Parvathaneni NK,Alterio V,van Kuijk SJA,Monti SM,Lambin P,De Simone G,Supuran CT,Winum JY.J Med Chem,2013,56:8512-8520
45 Yao YF,Wang ZC,Wu SY,Li QF,Yu C,Liang XY,Lv PC,Duan YT,Zhu HL.Biochem Pharmacol,2017,137:10-28
46 Cao D,Liu Y,Yan W,Wang C,Bai P,Wang T,Tang M,Wang X,Yang Z,Ma B,Ma L,Lei L,Wang F,Xu B,Zhou Y,Yang T,Chen L.J Med Chem,2016,59:5721-5739
47 Duan YT,Sang YL,Makawana JA,Teraiya SB,Yao YF,Tang DJ,Tao XX,Zhu HL.Eur J Med Chem,2014,85:341-351
48 Duan YT,Yao YF,Tang DJ,Thumar N,Teraiya SB,Makawana JA,Sang YL,Wang ZC,Tao XX,Jiang AQ,Zhu HL.RSC Adv,2014,4:20382-20392
49 Duan YT,Yao YF,Huang W,Makawana JA,Teraiya SB,Thumar NJ,Tang DJ,Tao XX,Wang ZC,Jiang AQ,Zhu HL.Bioorg Med Chem,2014,22:2947-2954
50 Mazuryk O,Suzenet F,Kieda C,Brindell M.Metallomics,2015,7:553-566
51 Cheng Y,Wang H,Dinesh A,Zhou C.Chin J Org Chem,2016,36:1-42(in Chinese)[程宇,王辉,Dinesh A,周成合.有机化学,2016,36:1-42
52 B?aszczak-?wi?tkiewicz K,Olszewska P,Mikiciuk-Olasik E.Acta Biochim Pol,2013,60:427-433
53 Albada B,Metzler-Nolte N.Acc Chem Res,2017,50:2510-2518
54 Cui SF,Ren Y,Zhang SL,Peng XM,Damu GLV,Geng RX,Zhou CH.Bioorg Med Chem Lett,2013,23:3267-3272
55 Peng XM,Cai GX,Zhou CH.Curr Top Med Chem,2013,13:1963-2010
56 Gao WW,Gopala L,Bheemanaboina RRY,Zhang GB,Li S,Zhou CH.Eur J Med Chem,2018,146:15-37
57 Li D,Bheemanaboina RRY,Battini N,Tangadanchu VKR,Fang XF,Zhou CH.MedChemComm,2018,9:1529-1537
58 Gao WW,Rasheed S,Tangadanchu VKR,Sun Y,Peng XM,Cheng Y,Zhang FX,Lin JM,Zhou CH.Sci China Chem,2017,60:769-785
59 Maddili SK,Li ZZ,Kannekanti VK,Bheemanaboina RRY,Tuniki B,Tangadanchu VKR,Zhou CH.Bioorg Med Chem Lett,2018,28:2426-2431
60 Anthwal A,Rawat DS,Rawat MSM.Res J Chem Sci,2013,3:104-113
61 Li Y,Liu Y,Liu J,Liu J,Tang H,Cao C,Zhao D,Ding Y.Sci Rep,2015,5:7699
62 Rawat S,Warade S,Lahoti S.Curr Pharm Res,2010,1:60-69
63 Peng XM,Damu GLV,Zhou H.Curr Pharm Des,2013,19:3884-3930
64 Peng XM,Kumar KV,Damu GLV,Zhou CH.Sci China Chem,2016,59:878-894
65 Damu GLV,Cui SF,Peng XM,Wen QM,Cai GX,Zhou CH.Bioorg Med Chem Lett,2014,24:3605-3608
66 Cao Q,Wang H,Tangadanchu VKR,Gopala L,Zhou C.Sci Sin Chim,2017,47:844-858(in Chinese)[曹泉诚,王辉,Tangadanchu VKR,Gopala L,周成合.中国科学:化学,2017,47:844-858]
67 Peng XM,Peng LP,Li S,Avula SR,Kannekanti VK,Zhang SL,Tam KY,Zhou CH.Future Med Chem,2016,8:1927-1940
68 Cui SF,Addla D,Zhou CH.J Med Chem,2016,59:4488-4510
69 Cheng Y,Avula SR,Gao WW,Addla D,Tangadanchu VKR,Zhang L,Lin JM,Zhou CH.Eur J Med Chem,2016,124:935-945
70 Zhang L,Addla D,Ponmani J,Wang A,Xie D,Wang YN,Zhang SL,Geng RX,Cai GX,Li S,Zhou CH.Eur J Med Chem,2016,111:160-182
71 Gao WW,Zhou CH.Future Med Chem,2017,9:1461-1464
72 Cui SF,Peng LP,Zhang HZ,Rasheed S,Vijaya Kumar K,Zhou CH.Eur J Med Chem,2014,86:318-334
73 Li Q,Xing J,Cheng H,Wang H,Wang J,Wang S,Zhou J,Zhang H.Chem Biol Drug Des,2015,85:79-90
74 Zhang L,Kumar KV,Rasheed S,Geng RX,Zhou CH.Chem Biol Drug Des,2015,86:648-655
75 Banerjee S,Veale EB,Phelan CM,Murphy SA,Tocci GM,Gillespie LJ,Frimannsson DO,Kelly JM,Gunnlaugsson T.Chem Soc Rev,2013,42:1601-1618
76 Gong HH,Addla D,Lv JS,Zhou CH.Curr Top Med Chem,2016,16:3303-3364
77 Luo YL,Baathulaa K,Kannekanti VK,Zhou CH,Cai GX.Sci China Chem,2015,58:483-494
78 Zhang YY,Mi JL,Zhou CH,Zhou XD.Eur J Med Chem,2011,46:4391-4402
79 Damu GLV,Wang QP,Zhang HZ,Zhang YY,Lv JS,Zhou CH.Sci China Chem,2013,56:952-969
80 Lv JS,Peng XM,Kishore B,Zhou CH.Bioorg Med Chem Lett,2014,24:308-313
81 Gopikrishna P,Meher N,Iyer PK.ACS Appl Mater Interfaces,2018,10:12081-12111
82 Kang J,Tangadanchu VKR,Gopala L,Gao WW,Cheng Y,Liu HB,Geng RX,Li S,Zhou CH.Chin Chem Lett,2017,28:1369-1374
83 Kang J,Gopala L,Reddy Tangadanchu VK,Gao WW,Zhou CH.Future Med Chem,2018,10:711-724
84 Zhang F,Zhou C,Yan J.Chin J Org Chem,2010,30,783-796(in Chinese)[张飞飞,周成合,颜建平.有机化学,2010,30:783-796]
85 G?uszyńska A.Eur J Med Chem,2015,94:405-426
86 Li L,Chen Z,Zhang X,Jia Y.Chem Rev,2018,118:3752-3832
87 Zhang Y,Tangadanchu VKR,Bheemanaboina RRY,Cheng Y,Zhou CH.Eur J Med Chem,2018,155:579-589
88 Zhang Y,Tangadanchu VKR,Cheng Y,Yang RG,Lin JM,Zhou CH.ACS Med Chem Lett,2018,9:244-249
89 Li ZZ,Gopala L,Tangadanchu VKR,Gao WW,Zhou CH.Bioorg Med Chem,2017,25:6511-6522
90 Wang ZC,Duan YT,Qin YJ,Wang PF,Luo Y,Wen Q,Yang YA,Sun J,Hu Y,Sang YL,Zhu HL.Eur J Med Chem,2013,65:456-463
91 Cai J,Lu Y,Gan L,Zhang Y,Zhou C.Chin J Antibiot,2009,34:454-462(in Chinese)[蔡佳利,卢一卉,甘淋玲,张奕奕,周成合.中国抗生素杂志,2009,34:454-462]
92 Gan L,Cai J,Zhou C.Chin Pharm J,2009,44:1361-1367(in Chinese)[甘淋玲,蔡佳利,周成合.中国药学杂志,2009,44:1361-1367]
93 Wang SF,Yin Y,Qiao F,Wu X,Sha S,Zhang L,Zhu HL.Bioorg Med Chem,2014,22:2409-2415
94 Varshney V,Mishra NN,Shukla PK,Sahu DP.Eur J Med Chem,2010,45:661-666
95 Jeyakkumar P,Liu HB,Gopala L,Cheng Y,Peng XM,Geng RX,Zhou CH.Bioorg Med Chem Lett,2017,27:1737-1743
96 Wen SQ,Jeyakkumar P,Avula SR,Zhang L,Zhou CH.Bioorg Med Chem Lett,2016,26:2768-2773
97 Zhang SL,Chang JJ,Damu GLV,Fang B,Zhou XD,Geng RX,Zhou CH.Bioorg Med Chem Lett,2013,23:1008-1012
98 Zhang L,Chang JJ,Zhang SL,Damu GLV,Geng RX,Zhou CH.Bioorg Med Chem,2013,21:4158-4169
99 Yu K,Zhou C,Li D.Chin Pharm J,2008,43:481-488(in Chinese)[于克贵,周成合,李东红.中国药学杂志,2008,43:481-488]
100 Zhou CH,Zhang YY,Yan CY,Wan K,Gan LL,Shi Y.Anti-Cancer Agents Med Chem,2010,10:371-395
101 Dingsdag SA,Yap BCM,Hunter N,Crossley MJ.Org Biomol Chem,2015,13:98-109
102 Guo X,Facchetti A,Marks TJ.Chem Rev,2014,114:8943-9021
103 Wang X,Wang X,Geng R,Zhou C.Chin J New Drugs,2010,19:2050-2059(in Chinese)[王小玲,王宪龙,耿蓉霞,周成合.中国新药杂志,2010,19:2050-2059]
104 Li Y,Zhao CP,Ma HP,Zhao MY,Xue YR,Wang XM,Zhu HL.Bioorg Med Chem,2013,21:3120-3126
105 Sangani CB,Makwana JA,Duan YT,Tarpada UP,Patel YS,Patel KB,Dave VN,Zhu HL.Res Chem Intermed,2015,41:10137-10149
106 Zhang FF,Gan LL,Zhou CH.Bioorg Med Chem Lett,2010,20:1881-1884
107 Addla D,Wen SQ,Gao WW,Maddili SK,Zhang L,Zhou CH.Med Chem Commun,2016,7:1988-1994
108 Gu W,Qiao C,Wang SF,Hao Y,Miao TT.Bioorg Med Chem Lett,2014,24:328-331
109 Yendapally R,Hurdle JG,Carson EI,Lee RB,Lee RE.J Med Chem,2008,51:1487-1491
110 Cherian PT,Wu X,Yang L,Scarborough JS,Singh AP,Alam ZA,Lee RE,Hurdle JG.J Antimicrob Chemother,2015,70:3061-3069
111 Wei J,Wang Y,Wang X,Zhou C,Ji Q.Chin Pharm J,2011,46:481-485(in Chinese)[魏金建,王艳,王宪龙,周成合,吉庆刚.中国药学杂志,2011,46:481-485]
112 Yin BT,Yan CY,Peng XM,Zhang SL,Rasheed S,Geng RX,Zhou CH.Eur J Med Chem,2014,71:148-159
113 Shi Y,Zhou CH.Bioorg Med Chem Lett,2011,21:956-960
114 Beena,Kumar N,Rohilla RK,Roy N,Rawat DS.Bioorg Med Chem Lett,2009,19:1396-1398
115 Mao WJ,Lv PC,Shi L,Li HQ,Zhu HL.Bioorg Med Chem,2009,17:7531-7536
116 Atia AJK.Molecules,2009,14:2431-2446
117 Wu YB,Xie D,Zang ZL,Zhou CH,Cai GX.Chem Commun,2018,54:4437-4440
118 Duan YT,Wang ZC,Sang YL,Tao XX,Teraiya SB,Wang PF,Wen Q,Zhou XJ,Ding L,Yang YH,Zhu HL.Eur J Med Chem,2014,76:387-396
119 Ashok Kumar T,Kishore Babu PN,Rama Devi B.Med Chem Res,2015,24:1351-1364
120 Cui S,Wang Y,Lv J,Damu G,Zhou C.Sci Sin Chim,2012,42:1105-1131(in Chinese)[崔胜峰,王艳,吕敬松,Damu GL,周成合.中国科学:化学,2012,42:1105-1131]
121 Seed A.Chem Soc Rev,2007,36:2046-2069
122 Chen YY,Gopala L,Bheemanaboina RRY,Liu HB,Cheng Y,Geng RX,Zhou CH.ACS Med Chem Lett,2017,8:1331-1335
123 Cui S,Zhou C,Geng R.Chin J Biochem Pharm,2012,33:311-315(in Chinese)[崔胜峰,周成合,耿蓉霞,吉庆刚.中国生化药物杂志,2012,33:311-315]
124 Hosseinzadeh N,Hasani M,Foroumadi A,Nadri H,Emami S,Samadi N,Faramarzi MA,Saniee P,Siavoshi F,Abadian N,Mahmoudjanlou Y,Sakhteman A,Moradi A,Shafiee A.Med Chem Res,2013,22:2293-2302
125 Zhang GB,Maddili SK,Tangadanchu VKR,Gopala L,Gao WW,Cai GX,Zhou CH.Sci China Chem,2018,61:557-568
126 Zhang HZ,Zhao ZL,Zhou CH.Eur J Med Chem,2018,144:444-492
127 Zhang H,Zhou C,Geng R,Ji Q.Chin J Org Chem,2011,31:1963-1976(in Chinese)[张慧珍,周成合,耿蓉霞,吉庆刚.有机化学,2011,31:1963-1976]
128 Khalaj A,Nakhjiri M,Negahbani AS,Samadizadeh M,Firoozpour L,Rajabalian S,Samadi N,Faramarzi MA,Adibpour N,Shafiee A,Foroumadi A.Eur J Med Chem,2011,46:65-70
129 Zhang HZ,Damu GLV,Cai GX,Zhou CH.Eur J Med Chem,2013,64:329-344
130 Liu HB,Gao WW,Tangadanchu VKR,Zhou CH,Geng RX.Eur J Med Chem,2018,143:66-84
131 Singh K,Okombo J,Brunschwig C,Ndubi F,Barnard L,Wilkinson C,Njogu PM,Njoroge M,Laing L,Machado M,Prudêncio M,Reader J,Botha M,Nondaba S,Birkholtz LM,Lauterbach S,Churchyard A,Coetzer TL,Burrows JN,Yeates C,Denti P,Wiesner L,Egan TJ,Wittlin S,Chibale K.J Med Chem,2017,60:1432-1448
132 Zhang HZ,Cui SF,Nagarajan S,Rasheed S,Cai GX,Zhou CH.Tetrahedron Lett,2014,55:4105-4109
133 Wang YN,Bheemanaboina RRY,Gao WW,Kang J,Cai GX,Zhou CH.ChemMedChem,2018,13:1004-1017
134 Al-Tel TH,Al-Qawasmeh RA.Eur J Med Chem,2010,45:5848-5855
135 He S,Ponmani J,Avula S,Zhang H,Zhou C.Sci Sin Chim,2016,46:823-847(in Chinese)[何世超,Ponmani J,Avula SR,王宪龙,张慧珍,周成合.中国科学:化学,2016,46:823-847]
136 Wang XL,Wan K,Zhou CH.Eur J Med Chem,2010,45:4631-4639
137 Zhang HZ,He SC,Peng YJ,Zhang HJ,Gopala L,Tangadanchu VKR,Gan LL,Zhou CH.Eur J Med Chem,2017,136:165-183
138 Wang X,Gan L,Min C,Zhou C.Sci Sin Chim,2011,41:451-460(in Chinese)[王宪龙,甘淋玲,闫聪彦,周成合.中国科学:化学,2011,41:451-460]
139 Zhang HZ,Jeyakkumar P,Vijaya Kumar K,Zhou CH.New J Chem,2015,39:5776-5796
140 Lai TT,Xie D,Zhou CH,Cai GX.J Org Chem,2016,81:8806-8815
141 Letafat B,Mohammadhosseini N,Asadipour A,Foroumadi A.E-J Chem,2011,8:1120-1123
142 El-Gohary NS,Shaaban MI.Eur J Med Chem,2017,137:439-449
143 Zhang HZ,Wei JJ,Vijaya Kumar K,Rasheed S,Zhou CH.Med Chem Res,2015,24:182-196
144 Wan K,Zhang Y,Zhou C,Zhou X,Geng R,Ji Q.Chin J Antibiot,2012,37:8-20(in Chinese)[万昆,张奕奕,周成合,周向东,耿蓉霞,吉庆刚.中国抗生素杂志,2012,37:8-20]
145 Zhang Y,Damu GLV,Cui SF,Mi JL,Tangadanchu VKR,Zhou CH.Med Chem Commun,2017,8:1631-1639
146 Edlind TD,Katiyar SK.Antimicrob Agents Chemother,2010,54:4733-4738
147 Zhang HZ,Damu G,Cai GX,Zhou CH.Curr Org Chem,2014,18:359-406
148 Fang XF,Li D,Tangadanchu VKR,Gopala L,Gao WW,Zhou CH.Bioorg Med Chem Lett,2017,27:4964-4969
149 Fang B,Zhou CH,Rao XC.Eur J Med Chem,2010,45:4388-4398
150 Zhang SL,Chang JJ,Damu GLV,Geng RX,Zhou CH.Med Chem Commun,2013,4:839-846
151 Duan JR,Liu HB,Jeyakkumar P,Gopala L,Li S,Geng RX,Zhou CH.Med Chem Commun,2017,8:907-916
152 Peng LP,Nagarajan S,Rasheed S,Zhou CH.Med Chem Commun,2015,6:222-229
153 Zhang L,Kumar KV,Geng RX,Zhou CH.Bioorg Med Chem Lett,2015,25:3699-3705
154 Zhang L,Kumar KV,Rasheed S,Zhang SL,Geng RX,Zhou CH.Med Chem Commun,2015,6:1303-1310
155 Zhang SL,Damu GLV,Zhang L,Geng RX,Zhou CH.Eur J Med Chem,2012,55:164-175
156 Wang YN,Bheemanaboina RRY,Cai GX,Zhou CH.Bioorg Med Chem Lett,2018,28:1621-1628
157 Ren Y,Zhang HZ,Zhang SL,Luo YL,Zhang L,Zhou CH,Geng RX.J Chem Sci,2015,127:2251-2260
158 Kus C,S?züd?nmez F,Altanlar N.Arch Pharm Chem Life Sci,2009,342:54-60
159 Bhutta ZA,Sommerfeld J,Lassi ZS,Salam RA,Das JK.Infect Dis Poverty,2014,3:21
160 Bala V,Chhonker YS.Eur J Med Chem,2018,143:232-243
161 Ravi J,Mohammad R,Sokindra K,Arun K.Pharm Res-Dordr,2016,14:1-13
162 Mandalapu D,Kushwaha B,Gupta S,Singh N,Shukla M,Kumar J,Tanpula DK,Sankhwar SN,Maikhuri JP,Siddiqi MI,Lal J,Gupta G,Sharma VL.Eur J Med Chem,2016,124:820-839
163 Kumar L,Jain A,Lal N,Sarswat A,Jangir S,Kumar L,Singh V,Shah P,Jain SK,Maikhuri JP,Siddiqi MI,Gupta G,Sharma VL.ACS Med Chem Lett,2012,3:83-87
164 Wang Y,Zhou C.Sci Sin Chim,2011,46:1429-1456(in Chinese)[王艳,周成合.中国科学:化学,2011,46:1429-1456]
165 Saadeh HA,Mosleh IM,Al-Bakri AG,Mubarak MS.Monatsh Chem,2010,141:471-478
166 Jarrad AM,Karoli T,Debnath A,Tay CY,Huang JX,Kaeslin G,Elliott AG,Miyamoto Y,Ramu S,Kavanagh AM,Zuegg J,Eckmann L,Blaskovich MAT,Cooper MA.Eur J Med Chem,2015,101:96-102
167 Wang QP,Zhang JQ,Damu GLV,Wan K,Zhang HZ,Zhou CH.Sci China Chem,2012,55:2134-2153
168 Wang Y,Damu GLV,Lv JS,Geng RX,Yang DC,Zhou CH.Bioorg Med Chem Lett,2012,22:5363-5366
169 Saadeh HA,Khasawneh MA,Abu-Zeid YA,El-Haty IA,Mubarak MS,Nsangou SP,Goyal K,Sehgal R,Marco-Contelles J,Samadi A.ChemistrySelect,2017,2:5684-5687
170 Papadopoulou MV,Bloomer WD,Rosenzweig HS,O'Shea IP,Wilkinson SR,Kaiser M,Chatelain E,Ioset JR.Bioorg Med Chem,2015,23:6467-6476
171 Hernández-Nú?ez E,Tlahuext H,Moo-Puc R,Torres-Gómez H,Reyes-Martínez R,Cedillo-Rivera R,Nava-Zuazo C,Navarrete-Vazquez G.Eur J Med Chem,2009,44:2975-2984
172 Samant BS,Sukhthankar MG.Bioorg Med Chem Lett,2011,21:1015-1018
173 Dunn LA,Burgess AG,Krauer KG,Eckmann L,Vanelle P,Crozet MD,Gillin FD,Upcroft P,Upcroft JA.Int J Antimicrob Agents,2010,36:37-42
174 Jarrad AM,Debnath A,Miyamoto Y,Hansford KA,Pelingon R,Butler MS,Bains T,Karoli T,Blaskovich MAT,Eckmann L,Cooper MA.Eur J Med Chem,2016,120:353-362
175 Zhang HZ,Lin JM,Rasheed S,Zhou CH.Sci China Chem,2014,57:807-822
176 Abid M,Agarwal SM,Azam A.Eur J Med Chem,2008,43:2035-2039
177 Gupta S,Yardley V,Vishwakarma P,Shivahare R,Sharma B,Launay D,Martin D,Puri SK.J Antimicrob Chemother,2015,70:518-527
178 Thompson AM,Blaser A,Palmer BD,Anderson RF,Shinde SS,Launay D,Chatelain E,Maes L,Franzblau SG,Wan B,Wang Y,Ma Z,Denny WA.Bioorg Med Chem Lett,2017,27:2583-2589
179 Dai LL,Zhang HZ,Nagarajan S,Rasheed S,Zhou CH.Med Chem Commun,2015,6:147-154
180 Tukulula M,Sharma RK,Meurillon M,Mahajan A,Naran K,Warner D,Huang J,Mekonnen B,Chibale K.ACS Med Chem Lett,2013,4:128-131
181 Pedada SR,Satam VS,Tambade PJ,Kandadai SA,Hindupur RM,Pati HN,Launay D,Martin D.Org Process Res Dev,2013,17:1149-1155
182 Kumar D,Negi B,Rawat DS.Future Med Chem,2015,7:1981-2003
183 Munagala G,Yempalla KR,Singh S,Sharma S,Kalia NP,Rajput VS,Kumar S,Sawant SD,Khan IA,Vishwakarma RA,Singh PP.Org Biomol Chem,2015,13:3610-3624
184 Yempalla KR,Munagala G,Singh S,Kour G,Sharma S,Chib R,Kumar S,Wazir P,Singh GD,Raina S,Bharate SS,Khan IA,Vishwakarma RA,Singh PP.ACS Med Chem Lett,2015,6:1059-1064
185 Upton AM,Cho S,Yang TJ,Kim Y,Wang Y,Lu Y,Wang B,Xu J,Mdluli K,Ma Z,Franzblau SG.Antimicrob Agents Chemother,2015,59:136-144
186 Kang YG,Park CY,Shin H,Singh R,Arora G,Yu C,Lee IY.Bioorg Med Chem Lett,2015,25:3650-3653
187 Rakesh,Bruhn DF,Scherman MS,Singh AP,Yang L,Liu J,Lenaerts AJ,Lee RE.Bioorg Med Chem Lett,2016,26:388-391
188 Sutherland HS,Blaser A,Kmentova I,Franzblau SG,Wan B,Wang Y,Ma Z,Palmer BD,Denny WA,Thompson AM.J Med Chem,2010,53:855-866
189 Sonopo MS,Venter K,Boyle G,Winks S,Marjanovic-Painter B,Zeevaart JR.J Label Compd Radiopharm,2015,58:23-29
190 Durdagi S,Aksoydan B,Erol I,Kantarcioglu I,Ergun Y,Bulut G,Acar M,Avsar T,Liapakis G,Karageorgos V,Salmas RE,Sergi B?,Alkhatib S,Turan G,Yigit BN,Cantasir K,Kurt B,Kilic T.Eur J Med Chem,2018,145:273-290
191 Meng J,Xu Q,Song Z,Ling L,Zhou C.Chin J Antibiot,2012,36:81-89(in Chinese)[孟江平,徐强,宋仲容,凌立新,周成合.中国抗生素杂志,2012,36:81-89]
192 Bali A,Bansal Y,Sugumaran M,Saggu JS,Balakumar P,Kaur G,Bansal G,Sharma A,Singh M.Bioorg Med Chem Lett,2005,15:3962-3965
193 Meng J,Geng R,Zhou C,Gan L.Chin J New Drugs,2009,18:1505-1514(in Chinese)[孟江平,耿蓉霞,周成合,甘淋玲.中国新药杂志,2009,18:1505-1514]
194 Zhu W,Da Y,Wu D,Zheng H,Zhu L,Wang L,Yan Y,Chen Z.Bioorg Med Chem,2014,22:2294-2302
195 Sun L,Ji L,Chao H.Sci Sin Chim,2017,47:133-143(in Chinese)[孙伶俐,计亮年,巢晖.中国科学:化学,2017,47:133-143]
196 Weissleder R,Pittet MJ.Nature,2008,452:580-589
197 Nieto E,Delgado M,Sobrado M,de Ceballos ML,Alajarín R,García-García L,Kelly J,Lizasoain I,Pozo MA,álvarez-Builla J.Eur J Med Chem,2015,101:604-615
198 Vercellino L,Groheux D,Thoury A,Delord M,Schlageter MH,Delpech Y,BarréE,Baruch-Hennequin V,Tylski P,Homyrda L,Walker F,Barranger E,HindiéE.Clin Nucl Med,2012,37:1065-1068
199 Zhou CH,Wang Y.Curr Med Chem,2012,19:239-280
200 Yu Q,Wang Z,Chen C,Liu S,Shi B.J Nuclear Radiochem,2015,37:385-392(in Chinese)[于倩,王振光,陈成成,刘思敏,石彬.核化学与放射化学,2015,37:385-392
201 Metran-Nascente C,Yeung I,Vines DC,Metser U,Dhani NC,Green D,Milosevic M,Jaffray D,Hedley DW.J Nucl Med,2016,57:361-366
202 Wanek T,Kreis K,Kri?kováP,Schweifer A,Denk C,Stanek J,Mairinger S,Filip T,Sauberer M,Edelhofer P,Traxl A,Muchitsch VE,Mereiter K,Hammerschmidt F,Cass CE,Damaraju VL,Langer O,Kuntner C.Bioorg Med Chem,2016,24:5326-5339
203 Beppu T,Terasaki K,Sasaki T,Fujiwara S,Matsuura H,Ogasawara K,Sera K,Yamada N,Uesugi N,Sugai T,Kudo K,Sasaki M,Ehara S,Iwata R,Takai Y.Mol Imag Biol,2014,16:127-135
204 Kumar P,Elsaidi HRH,Zorniak B,Laurens E,Yang J,Bacchu V,Wang M,Wiebe LI.ChemMedChem,2016,11:1638-1645
205 Zhou C,Zhang F,Gan L,Zhang Y,Geng R.Sci China Ser B:Chem,2009,39:208-252(in Chinese)[周成合,张飞飞,甘淋玲,张奕奕,耿蓉霞.中国科学B辑:化学,2009,39:208-252]
206 Zhou CH,Gan LL,Zhang YY,Zhang FF,Wang GZ,Jin L,Geng RX.Sci China Ser B-Chem,2009,52:415-458
207 Dai L,Cui S,Damu G,Zhou C.Chin J Org Chem,2013,33:224-244(in Chinese)[代玲玲,崔胜峰,Damu GL,周成合.有机化学,2013,33:224-244]
208 Luo Z,Zhu H,Lin X,Chu T,Luo R,Wang Y,Yang Z.Bioorg Med Chem Lett,2016,26:1397-1400
209 Wu Y,Hao G,Ramezani S,Saha D,Zhao D,Sun X,Sherry AD.Contrast Media Mol Imag,2015,10:465-472
210 Seelam SR,Lee JY,Lee YS,Hong MK,Kim YJ,Banka VK,Lee DS,Chung JK,Jeong JM.Bioorg Med Chem,2015,23:7743-7750
211 Ramogida CF,Pan J,Ferreira CL,Patrick BO,Rebullar K,Yapp DTT,Lin KS,Adam MJ,Orvig C.Inorg Chem,2015,54:4953-4965
212 Li N,Zhu H,Chu TW,Yang Z.Eur J Med Chem,2013,69:223-231
213 Yang Y,Ding J.Acta Pharm Sin,2016,51:1227-1232(in Chinese)[杨怡君,丁劲松.药学学报,2016,51:1227-1232]
214 Mallia MB,Kumar C,Mathur A,Sarma HD,Banerjee S.Nucl Med Biol,2012,39:1236-1242
215 North AJ,Hayne DJ,Schieber C,Price K,White AR,Crouch PJ,Rigopoulos A,O’Keefe GJ,Tochon-Danguy H,Scott AM,White JM,Ackermann U,Donnelly PS.Inorg Chem,2015,54:9594-9610
216 Gulaka PK,Rojas-Quijano F,Kovacs Z,Mason RP,Sherry AD,Kodibagkar VD.J Biol Inorg Chem,2014,19:271-279
217 Wang H,Jeyakkumar P,Nagarajan S,Meng J,Zhou C.Prog Chem,2015,27:704-743(in Chinese)[王辉,Jeyakkumar P,Nagarajan S,孟江平,周成合.化学进展,2015,27:704-743]
218 Zhou F,Zanganeh S,Mohammad I,Dietz C,Abuteen A,Smith MB,Zhu Q.Org Biomol Chem,2015,13:11220-11227
219 Xu Y,Zanganeh S,Mohammad I,Aguirre A,Wang T,Yang Y,Kuhn L,Smith MB,Zhu Q.J Biomed Opt,2013,18:066009
220 Ao X,Bright SA,Taylor NC,Elmes RBP.Org Biomol Chem,2017,15:6104-6108
221 Feng W,Wang Y,Chen S,Wang C,Wang S,Li S,Li H,Zhou G,Zhang J.Dyes Pigments,2016,131:145-153
222 Evans SM,Kim K,Moore CE,Uddin MI,Capozzi ME,Craft JR,Sulikowski GA,Jayagopal A.Bioconjug Chem,2014,25:2030-2037
223 Saini N,Varshney R,Tiwari AK,Kaul A,Ishar MPS,Mishra AK.RSC Adv,2015,5:97102-97112
224 Zhang J,Liu W,Wang B,Liu J.Sci Sin Chim,2018,48:231-242(in Chinese)[张鉴泽,刘文贤,王兵庆,刘军枫.中国科学:化学,2018,48:231-242]
225 Dong BX,Pan YM,Liu WL,Teng YL.Cryst Growth Des,2018,18:431-440
226 Yang J,Zhang YB,Liu Q,Trickett CA,Gutiérrez-Puebla E,Monge Má,Cong H,Aldossary A,Deng H,Yaghi OM.J Am Chem Soc,2017,139:6448-6455
227 Orsi A,Price DJ,Kahr J,Pillai RS,Sneddon S,Cao S,Benoit V,?ozińska MM,Cordes DB,Slawin AMZ,Llewellyn PL,Casely I,Ashbrook SE,Maurin G,Wright PA.CrystEngComm,2017,19:1377-1388
228 Ban Y,Li Y,Peng Y,Jin H,Jiao W,Liu X,Yang W.Chem Eur J,2014,20:11402-11409
229 Van der Perre S,Bozbiyik B,Lannoeye J,De Vos DE,Baron GV,Denayer JFM.J Phys Chem C,2015,119:1832-1839
230 Kasik A,Dong X,Lin YS.Microporous Mesoporous Mater,2015,204:99-105