Design, synthesis, anticancer activity and molecular docking analysis of novel dinitrophenylpyrazole bearing 1,2,3-triazoles

A novel series of dinitrophenylpyrazole bearing triazole scaffolds were designed and synthesized with appreciable yields. The structures of all the target molecules (9a-j) were confirmed and characterized by H-1 NMR, C-13 NMR, FT-IR and HR-MS spectral techniques. These novel molecules were tested for their anti-cancer activity (in vitro) using three tumor cell lines indicating breast adenocarcinoma (MCF-7), cervical carcinoma (HeLa), and human epithelial colorectal adenocarcinoma (Caco-2) via the MIT approach. Compounds 9e, 9f, and 9 h showed the high potency growth inhibitory activity against the HeLa cell line (IC50 = 4.0 mu M, 5.0 mu M and 6.0 mu M) higher than that of Combretastatin-A4 (IC50 = 9.0 mu M) as reference drug. Besides, compound 9 h was found to be highly potent against MCF-7 cell line IC50 value of 8.0 mu M. Additionally, in this manuscript, the structure-activity relationship (SAR) analysis is reported. Molecular docking studies also confirm the experimental findings and explains the most probable interaction pattern. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

A novel series of anti-cancer molecules with dinitrophenylpyrazole bearing triazole scaffolds were designed and synthesized, showing high potency growth inhibitory activity against cervical carcinoma and breast adenocarcinoma cell lines. Compound 9h demonstrated significant activity against both cell lines.