Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents

ABSTRACT

One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of –CH₂–R or –O–R/–N–R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10 µM concentration.

GRAPHICAL ABSTRACT

KEYWORDS:

• Anti-proliferative
• benzimidazole
• click reaction
• 1,2,3-triazole

Acknowledgments

Prasanna S. Ghalsasi thanks Department of Science and Technology, New Delhi (SR/S1/IC-43/2009) for financial support. IIS thanks JRF and SRF for UGC-BSR fellowship. The authors thank the National Cancer Institute for 60 human cancer cell line screenings in the NCI’s Developmental Therapeutics Program (DTP) in vitro cell line screening.

Conflict of interest

The authors declare no conflict of interest.