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 \(P\bar{1}\) where a = 9.352(3) Å, b = 11.002(3) Å, 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.