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Bioorg Med Chem Lett. 2008 Jan 15;18(2):586-95. Epub 2007 Nov 28.

From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part II: Acyclic replacements for the (3S)-3-benzylpiperidine in a series of potent CCR3 antagonists.

Author information

1
Bristol-Myers Squibb Company, R & D, PO Box 4000, Princeton, NJ 08543-4000, USA.

Abstract

Conformational analysis of the 3-benzylpiperidine in CCR3 antagonist clinical candidate 1 (BMS-639623) predicts that the benzylpiperidine may be replaced by acyclic, conformationally stabilized, anti-1,2-disubstituted phenethyl- and phenpropylamines. Ab initio calculations, enantioselective syntheses, and evaluation in CCR3 binding and chemotaxis assays of anti-1-methyl-2-hydroxyphenethyl- and phenpropylamine-containing CCR3 antagonists support this conformational correlation.

PMID:
18160284
DOI:
10.1016/j.bmcl.2007.11.087
[Indexed for MEDLINE]

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