Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol
文献类型：期刊论文
| 作者 | Zhao, Yu1; Guo, Na1; Lou, Li-Guang3 ; Cong, Yu-Wen2; Peng, Li-Yan1; Zhao, Qin-Shi1
|
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY
 |
| 出版日期 | 2008-05-01 |
| 卷号 | 16期号:9页码:4860-4871 |
| 关键词 | derivatives of taxchinin A and brevifoliol synthesis cytotoxicity SAR |
| ISSN号 | 0968-0896 |
| DOI | 10.1016/j.bmc.2008.03.041 |
| 文献子类 | Article |
| 英文摘要 | Twenty-one derivatives of taxchinin A (1) and brevifoliol (2) were synthesized and evaluated for cytotoxicity against human non-small lung cancer (A549) cell line. Nine derivatives showed potent activity with IC(50) values from 0.48 to 6.22 mu M. 5-Oxo-13-TBDMS-taxchinin A (11) and5-oxo-13,15-epoxy-13-epi-taxchinin A (15) are the most potent derivatives, with IC(50) at 0.48 and 0.75 mu M, respectively. The structure - activity relationship (SAR) of these compounds established that exocyclic unsaturated ketone at ring C is the key structural element for the activity, while the alpha,beta-unsaturated ketone positioned at ring A has no effect for the activity. The significant cytotoxicity of derivatives 11 and 15 may be due to the conformational change in the taxane rings. The 3D-QSAR study was conducted on this series of compounds, which provided optimal predictive comparative molecular field (CoM-FA) model with cross-validated r(2) (q(2)) value of 0.64. (c) 2008 Elsevier Ltd. All rights reserved. |
| WOS关键词 | RHINOVIRUS 3C PROTEASE ; BIOLOGICAL EVALUATION ; TAXOIDS ; INHIBITORS ; ANALOGS ; DESIGN ; TAXANE ; POTENT |
| WOS研究方向 | Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000255605600008 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/272923]  |
| 专题 | 药理学第一研究室 |
| 通讯作者 | Zhao, Qin-Shi |
| 作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China; 2.Acad Mil Med Sci, Inst Radiat Med, Beijing 100850, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 200032, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Zhao, Yu,Guo, Na,Lou, Li-Guang,et al. Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2008,16(9):4860-4871. |
| APA | Zhao, Yu,Guo, Na,Lou, Li-Guang,Cong, Yu-Wen,Peng, Li-Yan,&Zhao, Qin-Shi.(2008).Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol.BIOORGANIC & MEDICINAL CHEMISTRY,16(9),4860-4871. |
| MLA | Zhao, Yu,et al."Synthesis, cytotoxic activity, and SAR analysis of the derivatives of taxchinin A and brevifoliol".BIOORGANIC & MEDICINAL CHEMISTRY 16.9(2008):4860-4871. |
入库方式： OAI收割
来源：上海药物研究所
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