Synthesis, Characterization and Biological Application of Pyrazolo[1,5-a]pyrimidine Based Organometallic Re(I) Complexes

Abstract

The neutral rhenium(I) complexes (I-VI) of type [ReCl(CO) 3 L n ] {where L 1 = 7-phenyl-5-(pyridin-2-yl)pyrazolo[1,5-a] pyrimidine, L 2 = 7-(4-bromophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimi-dine, L 3 = 7-(4-chlorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L 4 = 7-(2-chlorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L 5 = 7-(4-methoxyphenyl)-5-(pyridin-2-yl)pyrazolo [1,5-a]pyrimidine, L 6 = 5-(pyridin-2-yl)-7-(p-tolyl)pyrazolo[1,5-a]py-rimidine} were synthesized and characterized by 13 C-APT, 1 H-NMR, IR, electronic spectra, magnetic moment and conductance measurement. The anti-proliferative activity on HCT116 cells by MTT assay suggests potent cytotoxic nature of complexes, some complexes even have better activity than standard drug cisplatin, oxaliplatin, and carboplatin. The complexes were found to have better antimicrobial activity compare to pyrazolo pyrimidine ligands. The theoretical study of compounds-DNA interactions was examined by molecular docking as a supportive tool to the experimental data, which suggests the groove mode of binding. The values of docking energy for compounds-DNA interaction were found in the range of-230.31 to-288.34 kJ/mol. The intrinsic binding constant values of complexes (1.1-3.5 × 10 5 M-1) were found higher than the ligands (0.32-1.8 × 10 5 M-1).

Synthesis and Antimicrobial Evaluation of Some New Pyrazolo[1,5-a]pyrimidine and Pyrazolo[1,5-c]triazine Derivatives Containing Sulfathiazole Moiety

“…It has been found that pyrazolopyrimidines 23,24 and pyrazolotriazines 25 have major biological and medical activities as adenine analogs, antagonists and antitumor agents. [26][27][28][29] Therefore, we intend to prepare analogues of these compounds from 5-aminopyrazole derivatives (3) in high yield.…”