Synthesis and nicotinic acetylcholine receptor affinity of bivalent tropane-3-carboxylates

Suhong Zhang, Sari Izenwasser, Dean Wade, Jie Cheng, Ying Liu, Liang Xu, Mark L. Trudell

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Abstract

(Chemical Equation Presented) A series of diol di-(tropane-3α- carboxylate) esters and diol di-(tropane-3β-carboxylate) esters were synthesized from 3-tropene-3-carboxylic acid and tropane-3β-carboxylic acid, respectively. The bivalent tropane-3-carboxylates were evaluated for their ability to inhibit [3H]cytisine binding at rat brain nicotinic acetylcholine receptors (nAChRs). In general the (3β,3β′)- isomers were more potent than (3α,3α′)-isomer and the (3β,3β′)-decyl derivative (n = 10, Ki = 145 nM) exhibited the most potent affinity for nAChRs of the series.

Original languageEnglish (US)
Pages (from-to)1425-1430
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume44
Issue number6
DOIs
StatePublished - Jan 1 2007

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ASJC Scopus subject areas

  • Organic Chemistry

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