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1 Polish Journal of Chemistry

1 2003

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Syntheses of a New Series of N-Amino-N"-(benzenesulphonyl)guanidine Derivatives with Potential Antitumor Activity

Sławiński J., Bednarski P., Grunert R., Reszka P.

Polish Journal of Chemistry

2003

Vol. 77 / nr 1

53-64

Syntheses of novel N-amino-N_-(benzenesulphonyl)guanidines (4a-h, 5a-g) from N- (benzenesulphonyl)cyanamide potassium salt and hydrazine derivatives are described. Compounds 4b, 5a-c and 5e were evaluated by in vitro assays of growth inhibition against several human tumor cell lines. The highest in vitro cytotoxic activities were found for 3-phenylamino-1-(2-benzylthio-4-chloro-5-methylbenzenesulphonyl)guanidine (5b) (IC50 = 2.35-8.14 _M) and 3-phenylamino-1-(4-chloro-2-ethoxycarbonylmethylthio- 5-methylbenzenesulphonyl)guanidine (5c) (IC50 = 2.74-10.6 _M), while other tested compounds (5a, 5e) showed the moderate cytotoxic activities.The molecular orbital calculation of the possible tautomeric forms of the benzenesulphonylguanidine derivatives were also presented.