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

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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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
Pages (from-to)1425-1430
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume44
Issue number6
StatePublished - Nov 1 2007

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Tropanes
Nicotinic Receptors
Carboxylic Acids
Isomers
Esters
Rats
Brain
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Zhang, S., Izenwasser, S. E., Wade, D., Cheng, J., Liu, Y., Xu, L., & Trudell, M. L. (2007). Synthesis and nicotinic acetylcholine receptor affinity of bivalent tropane-3-carboxylates. Journal of Heterocyclic Chemistry, 44(6), 1425-1430.

Synthesis and nicotinic acetylcholine receptor affinity of bivalent tropane-3-carboxylates. / Zhang, Suhong; Izenwasser, Sari E; Wade, Dean; Cheng, Jie; Liu, Ying; Xu, Liang; Trudell, Mark L.

In: Journal of Heterocyclic Chemistry, Vol. 44, No. 6, 01.11.2007, p. 1425-1430.

Research output: Contribution to journalArticle

Zhang, S, Izenwasser, SE, Wade, D, Cheng, J, Liu, Y, Xu, L & Trudell, ML 2007, 'Synthesis and nicotinic acetylcholine receptor affinity of bivalent tropane-3-carboxylates', Journal of Heterocyclic Chemistry, vol. 44, no. 6, pp. 1425-1430.
Zhang, Suhong ; Izenwasser, Sari E ; Wade, Dean ; Cheng, Jie ; Liu, Ying ; Xu, Liang ; Trudell, Mark L. / Synthesis and nicotinic acetylcholine receptor affinity of bivalent tropane-3-carboxylates. In: Journal of Heterocyclic Chemistry. 2007 ; Vol. 44, No. 6. pp. 1425-1430.
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