Overman rearrangement and Pomeranz-Fritsch reaction for the synthesis of benzoazepinoisoquinolones to discover novel antitumor agents
文献类型：期刊论文
| 作者 | Li, Bo4; Wang, Gaihong4; Yang, Mu3; Xu, Zhijian4 ; Zeng, Bubing2; Wang, Heyao4; Shen, Jingshan4; Chen, Kaixian1,4; Zhu, Weiliang4
|
| 刊名 | EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
 |
| 出版日期 | 2013-12 |
| 卷号 | 70页码:677-684 |
| 关键词 | Benzoazepinoisoquinolone N-Allylated 3-arylisoquinolone Overman rearrangement Pomeranz-Fritsch reaction Antitumor |
| ISSN号 | 0223-5234 |
| DOI | 10.1016/j.ejmech.2013.10.049 |
| 文献子类 | Article |
| 英文摘要 | The B-ring of Benzoazepinoisoquinolones 1a-b was successfully constructed by Pomeranz-Fritsch reaction. The key intermediates 5a-b could be transformed from 9a-b via Overman rearrangement. The bioassay showed that 11 compounds are more active than sorafenib (IC50 = 7.56 mu M) against A375 melanoma cell line, among which 1a, 5a, 8a and 10c with IC50 values of 0.59, 0.20, 0.17 and 0.11 mu M, respectively, showed potent cytotoxicity close to or even stronger than the anti-melanoma drug vemurafenib (IC50 = 0.18 mu M). In addition, 5a, 8a and 10c are more active than both vemurafenib and sorafenib on HCT116 colon cell line (IC50 values: 0.86, 0.65, 0.42, >30 and 5.65 mu M for 5a, 8a, 10c, vemurafenib and sorafenib). Therefore, these compounds are promising candidates for further drug development. (C) 2013 Elsevier Masson SAS. All rights reserved. |
| WOS关键词 | TOLUAMIDE-BENZONITRILE CYCLOADDITION ; ALKALOIDS ; PROTOBERBERINE ; 8-OXOBERBERINE ; INHIBITOR ; CANCER ; KINASE |
| 资助项目 | Ministry of Science and Technology[2012AA01A305] ; National Major Project[2012ZX09301001-004] ; National Major Project[2012ZX09103001-001] ; National Natural Science Foundation[81273435] ; National Natural Science Foundation[91013008] |
| WOS研究方向 | Pharmacology & Pharmacy |
| 语种 | 英语 |
| WOS记录号 | WOS:000330554400064 |
| 出版者 | ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277340]  |
| 专题 | 药物发现与设计中心 药理学第三研究室 |
| 通讯作者 | Zeng, Bubing |
| 作者单位 | 1.Shanghai Univ Tradit Chinese Med, Shanghai 201203, Peoples R China 2.E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China; 3.Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China; 4.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Li, Bo,Wang, Gaihong,Yang, Mu,et al. Overman rearrangement and Pomeranz-Fritsch reaction for the synthesis of benzoazepinoisoquinolones to discover novel antitumor agents[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2013,70:677-684. |
| APA | Li, Bo.,Wang, Gaihong.,Yang, Mu.,Xu, Zhijian.,Zeng, Bubing.,...&Zhu, Weiliang.(2013).Overman rearrangement and Pomeranz-Fritsch reaction for the synthesis of benzoazepinoisoquinolones to discover novel antitumor agents.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,70,677-684. |
| MLA | Li, Bo,et al."Overman rearrangement and Pomeranz-Fritsch reaction for the synthesis of benzoazepinoisoquinolones to discover novel antitumor agents".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 70(2013):677-684. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。