Syntheses of 1-(Phenylsulfonyl)-(1H,3H)-imidazol-2-one Derivatives with Potential Biological Activity

摘要

A series of l-(arylsulfonyl)-3-(2,2-dimethoxyethyl)ureas (2a-e) was obtained by the reaction of l-(phenylsulfonyl)ureas (1a-e) with aminoacetaldehyde dimethyl acetal in boiling dioxane.Cyclocondensation reactions of the l-(arylsulfonyl)-3-(2,2-dimethoxy-ethyl)ureas (2a-e) in 98% H_2SO_4 gave the appropriate l-(arylsulfonyl)-(lH,3H)-imidazol-2-ones (3a-e) in good yields.The subsequent reaction of 3a with methanesulfonyl- or 4-nitrophenylsulfonyl chlorides furnished the 3-(R~4-sulfonyl) derivatives 4 and 5,respectively.Preliminary screening data indicated that the compounds 3c-e,4 and 5 were inactive against three selected human tumor cell lines derived from Breast cancer (MCF7),Lung cancer (NCI-H460) and CNS cancer (SF-268).