Synthesis, molecular structure and anticancer activity of 1-allyl-3-amino-2-(4-chloro-2-mercaptobenzenesulphonyl)guanidine derivatives

A series of 3-allylamino-6-chloro-7-R-1.1-dioxo-1.4.2-benzodithiazines (2a-e) vas obtained by the reaction of 6-chloro-3-methylthio- 1.4.2-benzodithiazine-1. 1-dioxides (1a-e) with allylamine. Selective hydrazinolysis of the allylaminobenzodithiazines (2a-e) gave the appropriate 1-allyl 1-3-amino-2-(4-chloro-2-mercaptobenzenesulphonyl)guanidines (3a-e) in good yields. The reaction of 3a with dimethylsulphate under alkaline conditions provided the methylthio derivative 4. The structures of these compounds were confirmed on the basis of elemental analysis. spectral data (IR. H-1- and C-13-NMR) and X-ray analysis. Screening data indicated that the compounds 3a and 3d exhibited significant in vitro activities against numerous human tumour cell lines, whereas compounds 3b and 3c showed a moderate activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.