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Design, synthesis and binding affinity of acetylcholine carbamoyl analogues.

Abstract：

:A series of acetylcholine carbamoyl analogues, cyclised at the carbamate moiety or at the cationic head or at both, were tested for binding affinity at muscarinic and neuronal nicotinic receptors (nAChRs). While no muscarinic affinity was found, submicromolar Ki values, similar to that of carbachol, were measured at α4β2 nAChRs for the enantiomers of 5-dimethylaminomethyl- and 5-trimethylammoniomethyl-2-oxazolidinone, 2 and 2a, and for (S)-N-methylprolinol carbamate (S)-3. Methylation of oxazolidinone nitrogen of 2 and 2a and of N-methylprolinol nitrogen of (S)-3 and, even more, hybridization of cyclic carbamate substructure (oxazolidinone) with cyclic cationic head (N-methylpyrrolidine) markedly lower the nicotinic affinity. Docking results were consistent with SAR analysis highlighting the interaction capabilities of (R)-2a and (S)-3 and the negative effect of intracyclic nitrogen methylation and of double cyclisation.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Bolchi C,Valoti E,Binda M,Fasoli F,Ferrara R,Fumagalli L,Gotti C,Matucci R,Vistoli G,Pallavicini M

doi

10.1016/j.bmcl.2013.09.023

subject

Has Abstract

pub_date

2013-12-01 00:00:00

pages

6481-5

issue

23

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(13)01097-4

journal_volume

23

pub_type

杂志文章

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