Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists
文献类型：期刊论文
| 作者 | Feng, Dong-Zhi; Song, Yan-Li; Jiang, Xiao-Hua; Chen, Li; Long, Ya-Qiu |
| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2007 |
| 卷号 | 5期号:16页码:2690-2697 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/b707175b |
| 文献子类 | Article |
| 英文摘要 | Piperazinopiperidine amide analogs are among the most promising CCR5 antagonists. As an effective extension of a previously- reported methodology to synthesize such compounds, forward- and reverse- syntheses were successfully developed in which the convergent synthesis of the piperazinopiperidine nucleus, with a building block of 4- substituent- 4- aminopiperidine, served as a common key step. The two- way approach affords a comprehensive access to the piperazinopiperidine templated library with variation on the pharmacophore sites. Thus, a SAR study of our synthesized piperazinopiperidine- based CCR5 antagonists was conducted with respect to the structure and con. guration of the substituent on the piperazine ring. The S- con. guration of the benzylic- substituent is vital for the CCR5 binding, and the bulky or aryl substituent on the 2- position in the piperazine ring is detrimental to the activity. By using the forward- synthesis approach, the best compound in the chiral piperazine- based CCR5 antagonist series, Sch- D ( Vicriviroc), was conveniently synthesized in an excellent yield. |
| WOS关键词 | HIV-1 INHIBITORS ; DISCOVERY ; POTENT ; DERIVATIVES ; INFECTION ; DESIGN |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000248559900021 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/273415]  |
| 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, Ya-Qiu |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Biochem & Cell Biol, Shanghai 200031, Peoples R China |
| 推荐引用方式 GB/T 7714 | Feng, Dong-Zhi,Song, Yan-Li,Jiang, Xiao-Hua,et al. Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2007,5(16):2690-2697. |
| APA | Feng, Dong-Zhi,Song, Yan-Li,Jiang, Xiao-Hua,Chen, Li,&Long, Ya-Qiu.(2007).Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists.ORGANIC & BIOMOLECULAR CHEMISTRY,5(16),2690-2697. |
| MLA | Feng, Dong-Zhi,et al."Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists".ORGANIC & BIOMOLECULAR CHEMISTRY 5.16(2007):2690-2697. |
入库方式： OAI收割
来源：上海药物研究所
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