Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Isoxazole Derivatives as Centrally Acting Muscle Relaxants. III. Synthesis and Activity of Conformationally Restricted Analogs
TOCHIRO TATEE, KAZUHISA NARITA, SHUJI KURASHIGE, SHINJI ITO, HIROSHI MIYAZAKI, HIROSHI YAMANAKA, MICHINAO MIZUGAKI, TAKAO SAKAMOTO, HIDEOMI FUKUDA
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Keywords: muscle relaxant, isoxazole derivative, isoxazolo [5, 4-b] pyridine, structure-activity relationship, conformation, conformationally restricted analog, tolperisone, anticonvulsant, anemic decerebrate rigidity
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1987 Volume 35 Issue 9 Pages 3676-3690

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Abstract

Conformationally restricted analogs of muscle-relaxant 3-amino-2-methyl-N- (3-phenyl-5-isoxazolyl) propanamides (1) and 5- (3-aminopropylamino) -3-phenylisoxazoles (2) were prepared, and their muscle-relaxant and other pharmacological activities were tested and compared with those of the corresponding acyclic derivatives. 7- (3-Diethylamino-2-methylpropanoyl) -3-phenyl-4, 5, 6, 7-tetrahydroisoxazolo [5, 4-b] pyridine (8) exhibited muscle-relaxant and anticonvulsant activities comparable with those of corresponding acyclic derivatives, i.e. 3-diethylamino-2-methyl-N- (3-phenyl-5-isoxazolyl) propanamides (1e-g), but other types of compounds showed decreased activities. The preferred conformation of the present isoxazole derivatives for muscle-relaxant activity is discussed.
7-Benzyl-6-methyl-3-phenyl-4-pyrrolidino-4, 5, 6, 7-tetrahydroisoxazolo [5, 4-b] pyridine (3d) showed moderate central nervous system-depressant activity.

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