SYNTHESE ET STRUCTURE DE CHLOROETHYLSULFONYL-ET SULFOXYLUREES DERIVEES DE L'ISOCYANATE DE CHLOROSULFONYLE

Abstract

A partir de l'isocyanate de chlorosulfonyle (C.S.I.), réactif Néctrophile bifonctionnel, on accède à des 2-chloroéthylsulfonylurées et des 2-chloroéthoxysulfonylurées, sur le modèle de nitrososourées aux propriétés oncostatiques. Les composés obtenus, alkylants et carbamylants potentiels, ont été étudiés par IR, RMN, spectrométrie de Masse et diffraction des RX, et ont été soumis à une évaluation biologique.

Nitrosoureas, a major class of cytotoxics and oncostatics, present in clinical uses some secondary iatrogenic effects (e.g., thrombopeniae, myelotoxicity, mutagenicity …). In the field of research of alkylo-carbamoyling non-nitrosed compounds, are presented here two news series which associate ureido group with 2-chloroethyl substituant. Both title's compounds are synthetized from chlorosulfonyl isocyanate (C.S.I.), by regioselective methods. The structure are established by IR, NMR ¹H and ¹³C, Mass spectrometry and RX diffraction data. The biological evaluation towards L1210 does not show significant antimitotic properties for these ureas. This fact is certainly in connection with their polar confirmed structure.

Key Words:

• Chlorosulfonyl isocyanate
• Chloroethylsulfonylureas
• Chloroethylsulfoxylureas
• Crystallographic data
• antimitotic screening.