Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro- N-(4,5-dihydro-5-oxo-1 H-1,2,4-triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activity

Jarosław Sławiński; Beata Żołnowska; Czesława Orlewska; Jarosław Chojnacki

doi:10.1007/s00706-012-0849-7

Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro- N-(4,5-dihydro-5-oxo-1 H-1,2,4-triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activity

Monatsh Chem. 2012;143(12):1705-1718. doi: 10.1007/s00706-012-0849-7. Epub 2012 Sep 25.

Authors

Jarosław Sławiński¹, Beata Żołnowska¹, Czesława Orlewska¹, Jarosław Chojnacki²

Affiliations

¹ Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.
² Department of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80233 Gdańsk, Poland.

Abstract

Abstract: A series of novel 4-chloro-N-(4,5-dihydro-5-oxo-1-R²-1H-1,2,4-triazol-3-yl)-5-methyl-2-(R¹-methylthio)benzenesulfonamide derivatives have been synthesized as potential anticancer agents. The in vitro antitumor activity of some compounds was evaluated in the US National Cancer Institute (NCI) against the NCI-60 cell line panel. The most prominent compound showed remarkable activity against 13 human tumor cell lines representing lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast at low micromolar GI₅₀ level in the range of 1.9-3.0 μM.

Keywords: Anticancer; Cyclization; Isocyanate; Sulfonamide; Triazolone.