Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists

	Forward- and reverse-synthesis of piperazinopiperidine amide analogs: a general access to structurally diverse 4-piperazinopiperidine-based CCR5 antagonists
	Feng, DZ; Song, YL; Jiang, XH; Chen, L; Long, YQ
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2007
卷号	5 期号:16 页码:2690-2697
通讯作者	Long, YQ (reprint author), Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China.,yqlong@mail.shcnc.ac.cn
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.
学科主题	Chemistry
类目[WOS]	Chemistry, Organic
关键词[WOS]	HIV-1 INHIBITORS ; DISCOVERY ; POTENT ; DERIVATIVES ; INFECTION ; DESIGN
收录类别	SCI
语种	英语
WOS记录号	WOS:000248559900021
内容类型	期刊论文
版本	出版稿
源URL	[http://202.127.25.143/handle/331003/1625]
专题	上海生化细胞研究所_上海生科院生化细胞研究所
推荐引用方式 GB/T 7714	Feng, DZ,Song, YL,Jiang, XH,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, DZ,Song, YL,Jiang, XH,Chen, L,&Long, YQ.(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, DZ,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.