Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4: Synthesis and structure-activity relationships for 1-[N(methyl)-N-(phenylsulfonyl)amino]-2-(phenyl)-4-(4-(N-(alkyl)-N- (benzyloxycarbonyl)amino)piperidin-1-yl)butanes

Authors
Finke, PE Oates, B Mills, SG MacCoss, M Malkowitz, L Springer, MS Gould, SL DeMartino, JA Carella, A Carver, G Holmes, K Danzeisen, R Hazuda, D Kessler, J Lineberger, J Miller, M Schleif, WA Emini, EA
Citation
Pe. Finke et al., Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4: Synthesis and structure-activity relationships for 1-[N(methyl)-N-(phenylsulfonyl)amino]-2-(phenyl)-4-(4-(N-(alkyl)-N- (benzyloxycarbonyl)amino)piperidin-1-yl)butanes, BIOORG MED, 11(18), 2001, pp. 2475-2479
Citations number
15
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
18
Year of publication
2001
Pages
2475 - 2479
Database
ISI
SICI code
0960-894X(20010917)11:18<2475:AOTHCR>2.0.ZU;2-M
Abstract
(2S)-2-(3-Chlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[spiro(2,3 -dihydrobenzthiophene-3,4 ' -piperidin-1 ' -yl)]butane S-oxide (lb) has bee n identified as a potent CCR5 antagonist having an IC50 = 10 nM. Herein, st ructure-activity relationship studies of non-spiro piperidines are describe d, which led to the discovery of 4-(N-(alkyl)-N-(benzyloxy-carbonyl)amino)p iperidine derivatives (3-5) as potent CCR5 antagonists. (C) 2001 Elsevier S cience Ltd. All rights reserved.