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A novel  N2 -alkyl-3-thioxo-8-nitro-1,2,4-triazino[5,6- b ]indoles and 3-alkylated 3-thioxo-8-nitro-1,2,4-triazino[5,6- b ]indoles ( 2–13 ) were obtained by treatment of 8-nitro-1,2,4-triazino[5,6- b ]indole-3-(2 H, 5 H )thione ( 1 ) using various alkylating agents and different regioselective conditions. The chemical reactivity of compound  1  toward some nucleophilic and electrophilic compounds such as isothiocyanates, primary amines, and sulfonamides was investigated. The structures of the synthesized compounds were confirmed by spectral data and elemental analysis. The biological activity of the new compounds was tested and revealed the promising antibacterial activity of  6 ,  8 , and  4  were when Ampicillin was used as a reference.

Regioselective Synthesis of Some 3-Thioxo-8-Nitro-(2H)-1,2,4-Triazino[5,6- b ]Indole Derivatives and Their Antibacterial Activity