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Bioorg Med Chem Lett. 2006 Mar 1;16(5):1358-61. Epub 2005 Dec 5.

Synthesis and SAR of 1,2-trans-(1-hydroxy-3-phenylprop-1-yl)cyclopentane carboxamide derivatives, a new class of sodium channel blockers.

Author information

1
Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA. dong_ok@merck.com

Abstract

Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na(V)1.7 and off-target activity against the cardiac potassium channel hERG. The stereochemistry of the hydroxyl group and substitution on the phenyl rings with either fluorinated O-alkyl or alkyl groups were found to be critical for conferring potency against Na(V)1.7. A benchmark compound from this series displayed efficacy in rat models of inflammatory and neuropathic pain.

PMID:
16337121
DOI:
10.1016/j.bmcl.2005.11.051
[Indexed for MEDLINE]

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