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

Abstract

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-(2H,5H)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.

Keywords:

• Alkylation
• antibacterial
• synthetic
• 3-thioxo-124-triazino[56-b]indole

Acknowledgments

The authors would like to thank DSc. Prof Reda M. Abdel-Rahman, for all his generous effort and support to present this work. Thanks to Dr. I. Ismail, Biochemistry. Ain shams university, Egypt, for biological screening.

Disclosure statement

There are no conflicts of interest.