Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists
文献类型：期刊论文
| 作者 | Gao, Linghuan1,2; Li, Min1; Meng, Tao1 ; Peng, Hongli1; Xie, Xin1; Zhang, Yongliang1; Jin, Yu1; Wang, Xin1; Zou, Libo2; Shen, Jingkang1
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| 刊名 | EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
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| 出版日期 | 2011-11 |
| 卷号 | 46期号:11页码:5310-5316 |
| ISSN号 | 0223-5234 |
| 关键词 | Anti-obesity CB1 receptor Antagonist Asymmetric synthesis Enantiomer |
| DOI | 10.1016/j.ejmech.2011.08.030 |
| 文献子类 | Article |
| 英文摘要 | We recently discovered and reported a novel series of benzhydrylpiperazine derivatives bearing an asymmetric carbon atom that are potent and selective hCB1 inverse agonists. In the present study, we used Davis-Ellmann-type sulfonamide chemistry to asymmetrically synthesize two enantiomers of the most potent racemic N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide [14]. Enantiomer separation and configuration assignment were carried out. Our results indicate that the R-configuration is the more active enantiomer, displaying enhanced antagonistic activity for hCB1 receptor, better oral bioavailability, and greater efficacy in the reduction of body weight in diet-induced obese mice. (C) 2011 Elsevier Masson SAS. All rights reserved. |
| WOS关键词 | TERT-BUTANESULFINYL IMINES ; CB1 RECEPTOR ; FOOD-INTAKE ; RIMONABANT ; WEIGHT ; DISCOVERY ; EFFICACY ; AMINES ; DRUG |
| 资助项目 | 863 Program (National High Technology Research and Development Program of China)[2007AA02Z308] ; National Natural Science Foundation of China[81001355] ; National Natural Science Foundation of China[30873162] ; Shanghai Commission of Science and Technology[08JC1407701] |
| WOS研究方向 | Pharmacology & Pharmacy |
| 语种 | 英语 |
| 出版者 | ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER |
| WOS记录号 | WOS:000298120500007 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278342]  |
| 专题 | 药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Meng, Tao |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Shenyang Pharmaceut Univ, Sch Life Sci & Biopharmaceut, Dept Pharmacol, Shenyang 110016, Peoples R China |
| 推荐引用方式 GB/T 7714 | Gao, Linghuan,Li, Min,Meng, Tao,et al. Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2011,46(11):5310-5316. |
| APA | Gao, Linghuan.,Li, Min.,Meng, Tao.,Peng, Hongli.,Xie, Xin.,...&Shen, Jingkang.(2011).Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,46(11),5310-5316. |
| MLA | Gao, Linghuan,et al."Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 46.11(2011):5310-5316. |
入库方式： OAI收割
来源：上海药物研究所
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