Analogues of Capsaicin with Agonist Activity as Novel Analgesic Agents; Structure—Activity Studies. 3. The Hydrophobic Side-Chain “C-Region”

Christopher S.J. Walpole, Roger Wrigglesworth, Stuart Bevan, Elizabeth A. Campbell, Andy Dray, Iain F. James, Kay J. Masdin, Martin N. Perkins, Janet Winter

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Abstract

Structural variants of the hydrophobic side chain (“C region”) of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (45Ca2+ influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the “C-region” of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.

Original languageEnglish
Pages (from-to)2381-2389
Number of pages9
JournalJournal of Medicinal Chemistry
Volume36
Issue number16
DOIs
StatePublished - 1993
Externally publishedYes

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