Syntheses and Anti-histaminic and Anti-allergic Activities of Hexahydro-4-hydroxy-1-benzofuran-2-ones

• Published in: Chemical & pharmaceutical bulletin Vol. 32; no. 6; pp. 2249 - 2261
• Main Authors: TAKEUCHI, NAOKI, KASAMA, TOSHIO, IKEDA, RIKA, SHIMIZU, KAZUE, HATAKEYAMA, KUMIKO, AIDA, YOKO, KANEKO, YOKO, TOBINAGA, SEISHO
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01.01.1984; Maruzen; Japan Science and Technology Agency
• Subjects: Animals; Benzofurans - chemical synthesis; Benzofurans - pharmacology; Chemical Phenomena; Chemistry; Exact sciences and technology; Guinea Pigs; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Histamine Antagonists - chemical synthesis; Hypersensitivity - prevention & control; In Vitro Techniques; Male; Muscle Contraction - drug effects; Muscle, Smooth - drug effects; Organic chemistry; Passive Cutaneous Anaphylaxis - drug effects; Preparations and properties; Rats; Rats, Inbred Strains; Schultz-Dale reaction; Schultz Dale reaction; Bicyclic compound; Lactone; Dehydration; Oxygen heterocycle; Antihistaminic; Biological activity; Antiallergic
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.32.2249

The hexahydro-4-hydroxy-1-benzofuran-2-ones 3a, 4a, and 5a (related to the 6β-hydroxyeremophilenolides 1 and 2, which show anti-histaminic and anti-allergic activities) were synthesized from dimedone through the compounds 18a, 23a, and 24a, followed by dehydration reactions. Pharmacological investigations of 3a, 4a, 5a, 18a, 23a, and 24a showed that compounds 4a and 5a have anti-histaminic activity and cause marked inhibition in the Schultz-Dale reaction.