Molecular modification of anticholinergics as probes for muscarinic receptors. 1. Amino esters of .alpha.-substituted phenylacetic acid and related analogs

Two series of compounds having the general structure of C6H5CRR'COOCH2CH2NEt2 were synthesized and examined for their antispasmodic activities. These compounds were selected as structural probes for exploring the nature of muscarinic cholinergic receptor binding sites that interact with atropin...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1987-02, Vol.30 (2), p.273-278
Main Authors: Lu, Matthias C, Wung, Walley E, Shih, Lisa B, Callejas, Soledad, Gearien, James E, Thompson, Emmanuel B
Format: Article
Language:English
Subjects:
Alkylation
Animals
Esters - chemical synthesis
Esters - pharmacology
Ethanolamines - chemical synthesis
Ethanolamines - pharmacology
Indicators and Reagents
Kinetics
Magnetic Resonance Spectroscopy
Male
Mass Spectrometry
Muscle Contraction - drug effects
Muscle, Smooth - physiology
Parasympatholytics - chemical synthesis
Phenylacetates - chemical synthesis
Phenylacetates - pharmacology
Rats
Rats, Inbred Strains
Receptors, Muscarinic - drug effects
Receptors, Muscarinic - metabolism
Structure-Activity Relationship
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Summary:Two series of compounds having the general structure of C6H5CRR'COOCH2CH2NEt2 were synthesized and examined for their antispasmodic activities. These compounds were selected as structural probes for exploring the nature of muscarinic cholinergic receptor binding sites that interact with atropine-like anticholinergics. These studies indicate a rather strict size limitation for the hydrophobic region of the receptor and suggest intramolecular hydrogen bonding as a possible means to explain the observed stereoselectivity.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00385a008