Synthesis, Crystal structure, Anticancer evaluation and Hirshfeld surface analysis of novel antipyrine gathered bis-triazoles as breast adenocarcinoma inhibitors

Abstract

A series of novel substituted antipyrine attached bis-triazoles 7(a-h) were synthesized via coupling followed by click chemistry reaction. Their structure was established by means of physico-chemical spectral studies and a single-crystal X-ray diffraction analysis (7c and 7f). X-ray diffraction results exhibited that 7c and 7f were crystallized in triclinic space group P¯1 where a=9.352 (3), b=11.002 (3), c=14.616 (4) Å and also revealed that the bis-triazole ring formed by two terminal alkyne groups joined with substituted azides (6a-h). The Hirshfeld surface analysis of the crystal surface shows that the most contributions for H…H/H…H, C… H/H …C, N…H / H…N, O…H/H…O, and C …C interactions. Breast adenocarcinoma cell line used test the compounds anticancer effects by MTT assay. Compound 7f was found to be most promising scaffold, exhibiting a anticancer effect near to standard imatinib (IC50 at 25.03±0.01 mg). The results exhibited that these analogues could be lead compounds in search for new effective anticancer agents.