Synthesis of 2-(2-hydroxyalkylidene)cyclopentanones and their bio-antimutagenic activity.
2-(2-Hydroxyalkylidene)cyclopentanones (1) and 5-(2-hydroxyoctylidene)-2-cyclopentenone (2) were synthesized by the aldol reaction of cyclopentanone-enolate (3)/cyclopentenone-enolate (19) with 2-bromoalkanals (4)/2-bromooctanal (4c) and subsequent treatment of the products with sodium acetate. The stereochemistry of the condensation, substitution and elimination was elucidated. The bio-antimutagenic activity of 1 increased as the 2-hydroxyalkylidene group increased in length up to = CHCH(OH)C8H17.
Iriye
R
R
Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University, Nagano, Japan.
Nakamura
A
A
Takeshita
M
M
D016587:Antimutagenic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects / Q000235:genetics / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D013329:Structure-Activity Relationship; D014466:Ultraviolet Rays
D016587:Antimutagenic Agents; D003517:Cyclopentanes