Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis and Muscarinic Properties of (1S, 3R, 5R)-Trimethyl(1-methyl-6-oxabicyclo[3.1.0]hex-3-yl)methyl Ammonium Iodide
Mario GIANNELLAAlessandro PIERGENTILIMaria PIGINIWilma QUAGLIAGiovanni RAFAIANISeyed K. TAYEBATI
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1994 Volume 42 Issue 6 Pages 1286-1290

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Abstract

To acquire more information about the so-called "muscarinic subsite", compound 4 was synthesized and tested.The results show that in comparison with deoxamuscarine (23) the muscarinic potency of 4 on M2 and M3 subtypes is not significantly altered by the presence of an epoxidic function, which confirms the donor-acceptor hydrogen bonding charactor of this receptive site. Conversely, there is a negative influence on the transduction prosesses. In addition, a second hydroxylic function bound on the carbon carrying the terminal methyl of the fourth substituent on the nitrogen dramatically affects the muscarinic behavior; the resulting compounds (11-1) lack any agonist or antagonist activity.

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© The Pharmaceutical Society of Japan
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