分子多样性类天然杂环化合物的设计合成及生物活性研究
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摘要
多环吡啶、多环吲哚等天然杂环化合物具有优良的抗菌、抗肿瘤、抗HIV等生物活性。以天然药物分子为先导,采用多样性导向合成策略,简捷高效地设计合成具有分子多样性的类天然杂环化合物并进行生物活性研究,对研究开发自主知识产权的药物具有重要意义。
本文以杂环烯酮缩胺及硝基葡烯糖为主要合成砌块,设计合成三大类共十二类类天然杂环化合物,总计353个化合物。对部分化合物进行了抗菌、抗肿瘤、荧光及细胞成像等生物活性的研究。
一、多环毗啶类化合物的合成及性质
茚并喹啉类化合物：通过串联反应一步法合成分子多样性多环茚并喹啉化合物。产物经体外抗瘤活性筛选,其中10c和10r具有较好细胞毒活性(Scheme1)。
多环咕吨酮及双环吡啶类化合物：构建多环咕吨酮化合物库及双环吡啶化合物库并对其进行荧光光谱性质及细胞成像的研究。部分化合物具有较好的pH荧光探针性能及较好的生物相容性和细胞穿透性(Scheme2)。
吡啶并香豆素类化合物：构建吡啶并香豆素化合物库(Scheme3)。咪唑并吡啶类化合物：构建了咪唑并吡啶类化合物库(Scheme4)。
嘧啶/苯并二氮杂(?)类化合物：合成手性侧链嘧啶/苯并二氮杂(?)类化合物库(Scheme5)。
二、多环吲哚类化合物：螺环吲哚酮化合物和多卤代吲哚化合物的合成
螺环吲哚酮化合物：高立体/区域选择性合成螺环吲哚酮化合物库(Scheme6)。
多卤代吲哚化合物：构建了多卤代吲哚化合物库(Scheme7)。
三、α-位取代杂环烯酮缩胺的合成
2-亚磷酸二乙酯基杂环烯酮缩胺：发展了一种以Mn(OAc)2/KMnO4复合催化体系代替Mn(OAc)3合成2-亚磷酸二乙酯基二甲缩硫醚的方法(Scheme8)。
Z构型杂环烯酮缩胺化合物：构建了2-吡唑啉酮基杂环烯酮缩胺化合物库及2-香豆素基杂环烯酮缩胺化合物库(Scheme9)。
2-亚硝基杂环烯酮缩胺类化合物：发展了一种新型有机亚硝基化试剂并构建了2-亚硝基杂环烯酮缩胺化合物库(Scheme10)。
Natural heterocyclic products such as polycyclic pyridines and polycyclic indoles exhibit a broad range of biological activities, such as antibacterial, antitumor, anti-HIV, and so on. Based on the lead compounds of natural drug molecules, we focused on the design and synthesis of potent activities containing natural-like heterocycles via diversity-oriented synthesis strategies. Moreover, the biological characters of these natural-like heterocycles were evaluated. In thus, it is of great significant in the development of natural-like heterocyclic drugs which possess proprietary intellectual property.
In this thesis, twelve libraries of natural-like heterocycle compounds were rapidly constructed by heterocyclic ketene aminals (HKAs) and2-nitroglycals. Furthermore, the biological activities including antibacterial, antitumor, the properties of fluorescence and cell imaging of some target compounds have been evaluated.
Part one:Synthesis and characterization of polycyclic pyridines
Indenoquinoline compounds:We developed a novel one-pot cascade reaction for the preparation of molecular diversity indenoquinolines. The further preliminary antitumor activities have shown that10c and10r have good cytotoxicity (Scheme1).
Polycyclic xanthone and bicyclic pyridine compounds:In this study, the novel polycyclic xanthones and bicyclic pyridines were designed and synthesized. The fluorescence spectroscopy and cell imaging were studied. The results showed that parts of them have excellent pH-fluorescence properties as well as better biological compatibility and cell penetrating.
Chromeno[3,4-c]pyridine compounds:the library has been built (Scheme3).
Imidazopyridine compounds:the compound library has been constructed (Scheme4).
Pyrimidine/benzodiazepin compounds:the pyrimidine analogues compound with chiral side-chain library has been built (Scheme5).
Part two:Polycyclic indoles-synthesis of spirooxindole and halogenated indole compounds
Spirooxindole compounds:the compound library has been established with high stereo-and region-selectivity (Scheme6).
Halogenated indole compounds:the compound library has been constructed (Scheme7).
Part three:synthesis of a-substituent heterocyclic ketene aminals
The synthetic method of2-diethyl phosphate mercaptals in the presence of complex catalytic systems of Mn(OAc)2/KMnO4instead of Mn(OAc)3was developed (Scheme8).
Z configuration-substituent heterocycle ketene amines:the2-pyrazolone HKA compound library and the2-coumarin HKA compound library have been built (Scheme9).
2-Nitroso heterocyclic ketene amines:the protocol of construction of2-nitroso HKA compound library catalyzed by a novel organic nitro sating reagent was developed (Scheme10).
本文以杂环烯酮缩胺及硝基葡烯糖为主要合成砌块,设计合成三大类共十二类类天然杂环化合物,总计353个化合物。对部分化合物进行了抗菌、抗肿瘤、荧光及细胞成像等生物活性的研究。
一、多环毗啶类化合物的合成及性质
茚并喹啉类化合物：通过串联反应一步法合成分子多样性多环茚并喹啉化合物。产物经体外抗瘤活性筛选,其中10c和10r具有较好细胞毒活性(Scheme1)。
多环咕吨酮及双环吡啶类化合物：构建多环咕吨酮化合物库及双环吡啶化合物库并对其进行荧光光谱性质及细胞成像的研究。部分化合物具有较好的pH荧光探针性能及较好的生物相容性和细胞穿透性(Scheme2)。
吡啶并香豆素类化合物：构建吡啶并香豆素化合物库(Scheme3)。咪唑并吡啶类化合物：构建了咪唑并吡啶类化合物库(Scheme4)。
嘧啶/苯并二氮杂(?)类化合物：合成手性侧链嘧啶/苯并二氮杂(?)类化合物库(Scheme5)。
二、多环吲哚类化合物：螺环吲哚酮化合物和多卤代吲哚化合物的合成
螺环吲哚酮化合物：高立体/区域选择性合成螺环吲哚酮化合物库(Scheme6)。
多卤代吲哚化合物：构建了多卤代吲哚化合物库(Scheme7)。
三、α-位取代杂环烯酮缩胺的合成
2-亚磷酸二乙酯基杂环烯酮缩胺：发展了一种以Mn(OAc)2/KMnO4复合催化体系代替Mn(OAc)3合成2-亚磷酸二乙酯基二甲缩硫醚的方法(Scheme8)。
Z构型杂环烯酮缩胺化合物：构建了2-吡唑啉酮基杂环烯酮缩胺化合物库及2-香豆素基杂环烯酮缩胺化合物库(Scheme9)。
2-亚硝基杂环烯酮缩胺类化合物：发展了一种新型有机亚硝基化试剂并构建了2-亚硝基杂环烯酮缩胺化合物库(Scheme10)。
Natural heterocyclic products such as polycyclic pyridines and polycyclic indoles exhibit a broad range of biological activities, such as antibacterial, antitumor, anti-HIV, and so on. Based on the lead compounds of natural drug molecules, we focused on the design and synthesis of potent activities containing natural-like heterocycles via diversity-oriented synthesis strategies. Moreover, the biological characters of these natural-like heterocycles were evaluated. In thus, it is of great significant in the development of natural-like heterocyclic drugs which possess proprietary intellectual property.
In this thesis, twelve libraries of natural-like heterocycle compounds were rapidly constructed by heterocyclic ketene aminals (HKAs) and2-nitroglycals. Furthermore, the biological activities including antibacterial, antitumor, the properties of fluorescence and cell imaging of some target compounds have been evaluated.
Part one:Synthesis and characterization of polycyclic pyridines
Indenoquinoline compounds:We developed a novel one-pot cascade reaction for the preparation of molecular diversity indenoquinolines. The further preliminary antitumor activities have shown that10c and10r have good cytotoxicity (Scheme1).
Polycyclic xanthone and bicyclic pyridine compounds:In this study, the novel polycyclic xanthones and bicyclic pyridines were designed and synthesized. The fluorescence spectroscopy and cell imaging were studied. The results showed that parts of them have excellent pH-fluorescence properties as well as better biological compatibility and cell penetrating.
Chromeno[3,4-c]pyridine compounds:the library has been built (Scheme3).
Imidazopyridine compounds:the compound library has been constructed (Scheme4).
Pyrimidine/benzodiazepin compounds:the pyrimidine analogues compound with chiral side-chain library has been built (Scheme5).
Part two:Polycyclic indoles-synthesis of spirooxindole and halogenated indole compounds
Spirooxindole compounds:the compound library has been established with high stereo-and region-selectivity (Scheme6).
Halogenated indole compounds:the compound library has been constructed (Scheme7).
Part three:synthesis of a-substituent heterocyclic ketene aminals
The synthetic method of2-diethyl phosphate mercaptals in the presence of complex catalytic systems of Mn(OAc)2/KMnO4instead of Mn(OAc)3was developed (Scheme8).
Z configuration-substituent heterocycle ketene amines:the2-pyrazolone HKA compound library and the2-coumarin HKA compound library have been built (Scheme9).
2-Nitroso heterocyclic ketene amines:the protocol of construction of2-nitroso HKA compound library catalyzed by a novel organic nitro sating reagent was developed (Scheme10).
引文
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