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Synthesis of H-bonding probes of alpha7 nAChR agonist selectivity.

Abstract：

:The alpha7 subtype of the nicotinic acetylcholine receptor (nAChR) is the target of studies aimed at identifying features that will lead to the development of selective therapeutics. Five arylidine anabaseines, three with pyridine rings and two with the pyrrole rings, were synthesized in 35-65% yield via aldol condensation. The compounds are homologs of benzylidine anabaseine and were chosen for synthesis because they provide either a hydrogen bond acceptor (pyridines) or hydrogen bond donor (pyrroles) that may interact with the receptor within the benzylidine selectivity motif. Initial analysis of the new compounds at 100 microM concentration reveal that the two pyrrole anabaseines are good partial agonists of the alpha7 nAChR, having 40% of the efficacy of ACh, efficacy comparable to 4OH-GTS-21, and dramatically enhanced efficacy relative to the 2- and 4-pyridinyl compounds. The pyrrole compounds were confirmed to be alpha7 selective, displaying preference for this receptor over muscle and heteromeric neuronal receptor subtypes.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Wang J,Papke RL,Horenstein NA

doi

10.1016/j.bmcl.2008.11.044

subject

Has Abstract

pub_date

2009-01-15 00:00:00

pages

474-6

issue

2

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)01422-4

journal_volume

19

pub_type

杂志文章

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