Benzylpiperazine Derivatives. VI. Design and Syntheses of Vinylogs of 1-Benzyl-4-diphenylmethylpiperazine Derivatives and Their Cerebral Vasodilating Activities

• Published in: Chemical & pharmaceutical bulletin Vol. 35; no. 10; pp. 4124 - 4129
• Main Authors: OHTAKA, HIROSHI, KANAZAWA, TOSHIRO, ITO, KEIZO, TSUKAMOTO, GORO
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01.10.1987; Maruzen; Japan Science and Technology Agency
• Subjects: Animals; Benzylidene Compounds - chemical synthesis; Benzylidene Compounds - pharmacology; Benzylidene Compounds - toxicity; cerebral vasodilating activity; Cerebrovascular Circulation - drug effects; Chemical Phenomena; Chemistry; cinnamylpiperazine; cinnarizine; diphenylmethylpiperazine; Dogs; Exact sciences and technology; Female; flunarizine; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; lead development; Male; Organic chemistry; Piperazines - chemical synthesis; Piperazines - pharmacology; Piperazines - toxicity; Preparations and properties; Vasodilator Agents - chemical synthesis; Vasodilator Agents - toxicity; Chemical reduction; Nitrogen heterocycle; Six membered ring; Vinylic compound; Carboxamide; Benzenic compound; Cerebral vasodilator; Biological activity
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.35.4124

As a lead development based on the previous quantitative structure-activity relationship (QSAR) results on cerebral vasodilating activities of 1-benzyl-4-diphenylmethylpiperazines, 1- cinnamyl-4-diphenylmethylpiperazines having electron-donating groups on the cinnamyl moiety were designed. Two methods of synthesis were developed. As expected from the QSAR results, these compounds exhibited stronger potency and longer-lasting effect than cinnarizine and flunarizine.