As a part of our research on chemical and biological properties of 2-mercaptobenzenesulfonamides with potential anticancer and/or anti-HIV activities [1-4], the syntheses of N,S-substituted benzenesulfonamide derivatives were performed. Reactions of the previously described 2-(2-mercaptobenzenesulfonylimino)tetrahydropyrimidines [5] or 1-(2-mercaptobenzenesulfonyl)-2-imidazolidinone [6] with the appropriate 2-bromoacetophenones afforded 4-chloro-N-(tetrahydropyrimidin-2-ylidene) -5-methyl-2-[2-oxo-2-(4-R²-phenyl)ethylsulfanyl]benzenesulfonamides 1-3 and 1-{4-chloro-5-methyl-2-[2-oxo-2-(4-R²-phenyl)ethylsulfanyl]benzenesulfonyl}imidazolidin-2- ones 4-5, respectively. The subsequent reactions of sulfonamides 1-3 with suitable semicarbazones or hydrazines and 4,5 with hydrazines led to the target title compounds of type A, B and C. The structures of new compounds were determined by analytical and spectral methods.

Ten of the obtained compounds were screened at Institute of Pharmacy University of Greifswald for their in vitro activity against a panel of 12 human cancer cell lines. The prominent benzenesulfonamide showed the selective activity toward cell lines of bladder cancer (IC₅₀ values in range 2.9-8.1 μM).

References
[1] E. Pomarnacka, Acta Polon. Pharm.Drug Research, 55, 1998, 481-486.
[2] E. Pomarnacka, A. Kornicka, Farmaco, 56, 2001, 571-577.
[3] Z. Brzozowski, J. Sławiński, Polish J. Chem., 80, 2006, 1807-1815.
[4] E. Pomarnacka, Polish J. Chem., 81, 2007, 345-352.
[5] E. Pomarnacka Acta Polon. Pharm. Drug Research, 53, 1996, 373-378.
[6] E. Pomarnacka, Sci. Pharm. 55,1987 Wien,121-126.

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1. SYNTHESIS AND ANTI-HIV ACTIVITY OF 4-CHLORO-2-MERCAPTO-N-(1,4,5,6-TETRA- HYDRO-1,2,4-TRIAZIN-3-YL)BENZENESUL- FONAMIDES
2. SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL ACTIVITY OF COPPER (II) COMPLEXES WITH CHELATING BIDENTATE 2-SUBSTITUTED BENZIMIDAZOLE LIGANDS.