SYNTHESIS, REACTIONS, AND BIOLOGICAL ACTIVITY OF SOME TRIAZINE DERIVATIVES CONTAINING SULFA DRUG MOIETIES

2015 M. R. E. Aly*, **, #, A. A. Gobouri*, S. H. Abdel Hafez*, ***, and H. A. Saad*, ****

#E-mail: h_saadzag@yahoo.com

*Department of Chemistry, Faculty of Science, Taif University, Taif, 21974 Kingdom of Saudi Arabia;
**Department of Chemistry, Faculty of Applied Science, Port Said University, Port Said, Egypt;
***Department of Chemistry, Faculty of Science, Assiut University, Assiut, Egypt;
****Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511 Egypt

Received August 8, 2014; in final form February 13, 2015

Thienyl-triazine-sulphonamide conjugates were prepared from their precursor amines using triethyl orthoformate or ethyl chloroformate as cross coupling reagents. The progress of these reactions was investigated by spectral (IR, NMR, MS) and microanalytical techniques. The synthesized compounds were in vitro screened for antibacterial, antifungal, antioxidant, and anticancer activity. 4-[({[3-Mercapto-5-oxo-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-4(5H)-yl]imino}methyl)amino]-benzenesulfonamide turned out to be a powerful antibacterial agent, while all the compounds prepared were inactive against fungal species tested. 4-{[({8-Cyano-4-oxo-3-[2-(2-thienyl)vinyl]-4H,8H-[1,2,4]triazino[3,4-b][1,3,4]thiadiazin-7-yl}amino)(ethoxy)methyl]amino}benzenesulfonamide displayed in vitro promising cytotoxicity against Ehrlich ascites carcinoma cell line with concurrent attenuation of malonodinitrile and it was unique among other compounds being unable to increase glutathione S-transferase and reduced glutathione S-transferase activities. This compound exhibited also good antioxidant properties that together with its cytotoxicity nominated it for further investigation in cancer research.

Keywords: 1,2,4-triazine, triazinothiadiazine, triazinecarbonitrile, sulfa drugs, biological activity.