Evaluation of anticancer activity of 4-vinyl-1-arylsulfonylimidazolidinones

• Published in: Archives of pharmacal research Vol. 29; no. 9; pp. 721 - 727
• Main Authors: Kwak, Son-Hyok, Bang, Seong-Cheol, Seo, Hyun-Hee, Shin, Hye-Rim, Lee, Ki-Cheul, Hoang, Le Tuan Anh, Jung, Sang-Hun
• Format: Journal Article
• Language: English
• Published: Korea (South) 대한약학회 01.09.2006
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Drug Screening Assays, Antitumor; Humans; Hydantoins - chemical synthesis; Hydantoins - pharmacology; Spectrophotometry, Ultraviolet; Structure-Activity Relationship; Tetrazolium Salts; Thiazoles; Vinyl Compounds - chemical synthesis; Vinyl Compounds - pharmacology; 약학
• ISSN: 0253-6269; 1976-3786
• DOI: 10.1007/BF02974070

To continue exploration of structure activity relationship of novel 1-(indoline-5-sulfonyl)-4-phenylimidazolidinones (1) reported as anticancer agent with broad spectrum, three 1-(arylsulfonyl)-4-vinylimidazolidinones (2) were synthesized from methyl serinate (3) in 8 steps. Reaction of intermediate 2-phenoxycarbonylaminobut-3-enyl p-toluenesulfonate (10) with arylsulfonamide in the presence of potassium carbonate produced corresponding 2 and N-(4-vinyloxazolidin-2-yl)arylsulfonamide 11 in approximately equal ratio. This reaction is believed to undergo through urea intermediate 16 as shown in scheme 3. 1-Arylsufonyl-4-vinylimidazolidinones 2 show much reduced activity against human colon carcinoma (Colo205), human chronic myelogenous leukemia (K562), and human ovarian adenocarcinoma (SK-OV-3) and compatible activity against human lung carcinoma (A549) compared to 1. Therefore phenyl at 4-position should be the optimum planar motif for the activity of 1.