Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. IV. Modification of the Phenylpiperazino Moiety of 2- (Phenylpiperazino-alkoxyphenyl) thiazolidine-3-carbothioamides and the Corresponding Carboxamides
HIROYUKI NATE, AKISHIGE WATANABE, KENJI MATSUKI, ISAO INOUE, HISAO OHTSUKA, YASUO SEKINE, KUNIYUKI ODA, YASUSHI HONMA, AKIHIKO ISHIDA, TAKESHI KANNO, MIKIHIKO KONDA, HIDEO NAKAI, HIROSHI WADA, MIKIO TAKEDA, HIDEO YABANA, TAKU NAGAO
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Keywords: 2- (phenylpiperidinoalkoxyphenyl) thiazolidine-3-carbothioamide, 2- (phenylpiperidinoalkoxyphenyl) thiazolidine-3-carboxamide, 2- (tetrahydropyridylalkoxyphenyl) thiazolidine-3-carbothioamide, 2- (tetrahydropyridylalkoxyphenyl) thiazolidine-3-carboxamide, 2- (phenylhomopiperazinoalkoxyphenyl) thiazolidine-3-carboxamide, 2-phenylthiazolidine, structure-activity relationship, positive inotropic activity, cardiotonic agent
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1987 Volume 35 Issue 7 Pages 2825-2839

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Abstract

Examination of the structure-activity relationships of 2- (phenylpiperazinoalkoxyphenyl) -thiazolidine-3-carbothioamides and the corresponding carboxamides (1) as new cardiotonic agents was extended by the chemical modification of the phenylpiperazino moiety. The 4-phenylpiperidine (13), 4-phenyltetrahydropyridines (17), and related derivatives were prepared from the chlorides (10) through several intermediates (12, 14, and 16) and tested for cardiotonic activity. Generally, both the 4-phenylpiperidine (13) and 4-phenyltetrahydropyridine (17) derivatives exhibited potent positive inotropic activity comparable to that of 1. The N-phenylpiperidines (9) and amide derivatives (22, 25, and 28) exhibited no significant positive inotropy. This is also the case for the phenylpropylamines (29) and the ethylenediamines (30), which are pseudo-ring analogues of 1 with respect to the piperazine moiety. The activity of the homopiperazine derivative (23) was approximately one-thirtieth of that of the corresponding piperazine derivative (1). Thus, the presence of the six-membered, basic azacycloalkane ring (piperidine or piperazine) with a 4-phenyl group at the end of the alkoxy side chain appears to be essential for the appearance of potent positive inotropic activity in this series of compounds.

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