Triazole Antifungals. IV. Synthesis and Antifungal Activities of 3-Acylamino-2-aryl-2-butanol Derivatives

• Published in: Chemical & pharmaceutical bulletin Vol. 39; no. 10; pp. 2581 - 2589
• Main Authors: KONOSU, Toshiyuki, TAJIMA, Yawara, TAKEDA, Noriko, MIYAOKA, Takeo, KASAHARA, Mayumi, YASUDA, Hiroshi, OIDA, Sadao
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1991; Maruzen; Japan Science and Technology Agency
• Subjects: 1, 2, 4-triazole; 3-acylamino-2-aryl-1-(triazol-1-yl)-2-butanol; antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Candida albicans; Candida albicans - drug effects; Candida albicans - enzymology; Chemistry; Cytochrome P-450 Enzyme Inhibitors; cytochrome P-450 inhibitor; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; oral activity; Organic chemistry; Oxidoreductases - antagonists & inhibitors; Preparations and properties; Sterol 14-Demethylase; Structure-Activity Relationship; Triazoles - chemical synthesis; Triazoles - pharmacology; Five membered ring; Nitrogen heterocycle; Chlorine Organic compounds; Absolute configuration; Lactam; Bicyclic compound; Enzyme inhibitor; Alcohol; Carboxamide; Benzenic compound; Fluorine Organic compounds; Biological activity
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.39.2581

New triazole compounds were designed and synthesized as potential inhibitors of the fungal cytochrome P-450 14α-demethylase. In testing for antifungal activity against a mouse systemic Candida albicans infection, (2R, 3R)-3-acylamino-2-aroyl-2-butanol derivatives III exhibited remarkably high efficacy after oral or parenteral administration. The structure-activity relationships of these amidoalcohols were evaluated.