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Synthesis of 1‐Methyl‐5‐(pyrazol‐3‐ and ‐5‐yl‐ and 1, 2, 4‐triazol‐3‐ and 5‐yl)‐1, 2, 3, 6‐tetrahydropyridine Derivatives and Their Evaluation as Muscarinic Receptor Ligands
Author(s) -
Del Giudice Maria Rosaria,
Mustazza Carlo,
Borioni Anna,
Gatta Franco,
Tayebati Khosrow,
Amenta Francesco,
Tucci Paolo,
Pieretti Stefano
Publication year - 2003
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200390013
Subject(s) - chemistry , in vivo , pirenzepine , muscarinic acetylcholine receptor , cholinergic , stereochemistry , arecoline , in vitro , chemical synthesis , receptor , pharmacology , biochemistry , endocrinology , biology , microbiology and biotechnology
A series of 1‐methyl‐5‐(pyrazol‐3‐ and ‐5‐yl‐ and 1, 2, 4‐triazol‐3‐ and 5‐yl)‐1, 2, 3, 6‐tetrahydropyridine derivatives structurally related to arecoline were synthesized and evaluated on M 1 , M 2 , and M 3 muscarinic receptors using [ 3 H] pirenzepine and [ 3 H] NMS as ligands. The binding affinity depended on the position and size of the substituents. The most interesting compounds were further evaluated in functional studies on isolated organs and in vivo for cholinergic side effects. Compounds 5l and 6i good M 1 and M 3 antagonistic properties in vitro and were devoid of cholinergic side effects in vivo.