Benzylpiperazine Derivatives. II. Syntheses and Cerebral Vasodilating Activities of 1-[ (3-Alkyl-3-hydroxy-3-phenyl) propyl] -4-benzylpiperazine Derivatives

HIROSHI OHTAKA; YOSHIAKI FUJIMOTO; KENJI YOSHIDA; TOSHIRO KANAZAWA; KEIZO ITO; GORO TSUKAMOTO

doi:10.1248/cpb.35.2782

HIROSHI OHTAKA, YOSHIAKI FUJIMOTO, KENJI YOSHIDA, TOSHIRO KANAZAWA, KEIZO ITO, GORO TSUKAMOTO

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Keywords: piperazine, homopiperazine, benzylpiperazine, acylation, alkylation, Grignard reaction, cerebral vasodilator

JOURNAL FREE ACCESS

1987 Volume 35 Issue 7 Pages 2782-2791

DOI https://doi.org/10.1248/cpb.35.2782

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Abstract

Analogs of 1-[ (3-alkyl-3-hydroxy-3-phenyl) propyl]-4- (2, 3, 4-trimethoxybenzyl) piperazine (1) were prepared and tested for cerebral vasodilating activity. It was found that the potency depends positively on the number of methoxyl groups on the benzyl moiety, and the homopiperazine analogs seem to be equipotent to the corresponding piperazines.
From the standpoints of potency and ease of synthesis, 8k was selected for further study. Further analogs, which have various substituents in place of the benzyl moiety of 8k, were prepared and tested for cerebral vasodilating activity. These analogs were less potent than 8k. It was suggested that the benzyl moiety of 8k plays an important role in the high cerebral vasodilating activity.

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