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Paper | Regular issue | Vol 85, No. 11, 2012, pp.2723-2734
Published online, 26th September, 2012
DOI: 10.3987/COM-12-12568
Oximes of 3-Hydroxyprenylflavanones and Their Cytotoxic Activities

Sanit Thongnest, Ranu Sawangsri, Korakot Navakhun, Jantana Yahuafai, Pongpun Siripong, and Somyote Sutthivaiyakit*

*Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Ramkhamhaeng Road, Bangkapi, Bangkok 10240, Thailand

Abstract

Oximination of 3-hydroxyprenylflavanones using hydroxylamine hydrochloride yielded 4-hydroxy-3-oxime and 3-hydroxy-4-oxime derivatives. The 3β-O-acetylhydroxyprenylflavanones, under similar reaction condition, yielded corresponding 4-O-acetyl-3-oximes. The configurations at C-4 of the 4-hydroxy-3-oximes obtained from both 3α- and 3β-hydroxyprenylflavanones and of 4-O-acetyl-3-oxime derivative from 3β-O-acetylprenylflavanones were proposed. Cytotoxic activities of the oximes and their parent compounds were evaluated against a panel of human cancer cell lines.