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Synthesis, structural, conformational and pharmacological study of esters derived from 3‐methyl‐2,4‐diphenyl‐3‐azabicyclo[3.3.1]nonan‐9α‐ol as potential analgesics
Author(s) -
Iriepa I.,
GilAlberdi B.,
Galvez E.,
SanzAparicio J.,
Fonseca I.,
Orjales A.,
Berisa A.,
Labeaga C.
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199802)11:2<125::aid-poc979>3.0.co;2-#
Subject(s) - chemistry , stereochemistry , medicinal chemistry , computational chemistry , combinatorial chemistry
A series of esters derived from 3‐methyl‐2,4‐diphenyl‐3‐azabicyclo[3.3.1]nonan‐9α‐ol ( 1 ) was synthesized and studied by 1 H and 13 C NMR spectroscopy, and the crystal structure of 3‐methyl‐2,4‐diphenyl‐9α‐(3,5‐dimethylbenzoyloxy)‐3‐azabicyclo[3.3.1]nonane ( 2 ) was determined by x‐ray diffraction. The compounds studied display in CDCl 3 a preferred flattened chair–chair conformation. This bicycle conformation is similar to that found for 2 in the crystal state. Pharmacological assays on mice were performed to evaluate drug‐induced behavioral alteration, peripheral or central acute toxicity and analgesic activity. © 1998 John Wiley & Sons, Ltd.