Facile synthesis of 4-substituted-4-aminopiperidine derivatives, the key building block of piperazine-based CCR5 antagonists
文献类型：期刊论文
| 作者 | Jiang, XH; Song, YL; Long, YQ |
| 刊名 | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
 |
| 出版日期 | 2004-07-16 |
| 卷号 | 14期号:14页码:3675-3678 |
| 关键词 | 4-substituted-4-aminopiperidine piperazine-based CCR5 antagonist curtius rearrangement building block convergent synthesis HIV-1 entry inhibitor |
| ISSN号 | 0960-894X |
| DOI | 10.1016/j.bmcl.2004.05.014 |
| 文献子类 | Article |
| 英文摘要 | 4-Substituted-4-aminopiperidine is an interesting structural motif found in a number of bioactive compounds. An efficient and convenient method for the synthesis of 4-differently substituted-4-aminopiperidine derivatives was described, employing isonipecotate as a starting material and Curtius rearrangement as a key step. The alkylation of isonipecotate could introduce various substituents at the 4-position of the piperidine ring. With this key building block, we are able to efficiently synthesize piperazino-piperidine based CCR5 antagonist in a highly convergent manner free of using toxic reagents such as diethylaluminum cyanide. The concise synthesis of a potent bioavailable CCR5 antagonist as HIV-1 entry inhibitor, Sch-350634 (1) was accomplished in excellent yield using N'-Boc-4-methyl-4-aminopiperidine 5a as a smart building block. The new methodology provides a facile and practical access to the piperazino-piperidine amide analogs as HIV-1 entry inhibitors. (C) 2004 Elsevier Ltd. All rights reserved. |
| WOS关键词 | HIV-1 INHIBITORS ; RECEPTOR LIGANDS ; DISCOVERY ; PROGRESS |
| WOS研究方向 | Pharmacology & Pharmacy ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000222367300011 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/274045]  |
| 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 | Long, YQ |
| 作者单位 | CAS, Shanghai Inst Biol Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jiang, XH,Song, YL,Long, YQ. Facile synthesis of 4-substituted-4-aminopiperidine derivatives, the key building block of piperazine-based CCR5 antagonists[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2004,14(14):3675-3678. |
| APA | Jiang, XH,Song, YL,&Long, YQ.(2004).Facile synthesis of 4-substituted-4-aminopiperidine derivatives, the key building block of piperazine-based CCR5 antagonists.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,14(14),3675-3678. |
| MLA | Jiang, XH,et al."Facile synthesis of 4-substituted-4-aminopiperidine derivatives, the key building block of piperazine-based CCR5 antagonists".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 14.14(2004):3675-3678. |
入库方式： OAI收割
来源：上海药物研究所
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