Abstract
The neutral rhenium(I) complexes (I-VI) of type [ReCl(CO)3Ln-] where L1 = 7-phenyl-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L2 = 7-(4-bromophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimi- dine, L3 = 7-(4-chlorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L4 = 7-(2-chlorophenyl) -5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L5 = 7-(4-methoxyphenyl)-5-(pyridin-2-yl)pyrazolo [1,5-a]pyrimidine, L6 = 5-(pyridin-2-yl)-7-(p-tolyl)pyrazolo[1,5-a]pyrimidine were synthesized and characterized by 13C-APT, 1H-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, even some complexes have better activity than standard drug cisplatin, oxaliplatin, and carboplatin. The complexes 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 (1.1-3.5×105 M-1) were found higher than the ligands (0.32-1.8×105 M-1).
Highlights
Metal carbonyl moieties, such as {M(CO)3} (M= Cr, Mn, Re, Fe), can attach to the biomolecules capable of molecular recognition, to label and assay, specific biological receptors
[Co2(CO)6(HC2C-CH2O2CC6H4-2OH)] is more active than cisplatin on the human mammary tumor cell lines MCF-7 and MDA-MB-231.4 [{η5(4-Me2N{CH2}4OC6H4)-(4-HOC6H4)CHCHEtC5H4} Re(CO)3] has been shown to behave to tamoxifen, and it appears that the observed antiproliferative effect is dependent on the oestradiol receptor α
Materials and methods: All the chemicals and solvents were of reagent grade, 2-acetyl thiophene, substituted aldehyde were purchased from Merck Limited (India), different substituted phenyl hydrazine were purchased from Thirumalai Chemicals Ltd. (TCL), potassium-tert-butoxide, potassium hydroxide purchased from Sisco Research Laboratories Pvt
Summary
Metal carbonyl moieties, such as {M(CO)3} (M= Cr, Mn, Re, Fe), can attach to the biomolecules capable of molecular recognition, to label and assay, specific biological receptors. [Total signal observed = 16: signal of C = 6 (p‐CH3 phenyl ring‐C = 2, pyrazolo[1,5‐a]pyrimidine‐C = 3, pyridine ring‐C = 1), signal of CH = 9 (pyrazolo[1,5‐a]pyrimidine‐CH = 3, p‐CH3-phenylring‐CH = 2, pyridine ring‐ CH = 4), –CH3 = 1]; IR (KBr, 4000–400 cm– 1): 2923 ν(=C‐H)ar., 1551 ν(C=N), 1512 (C‐H) bending, 1196 ν(C‐N), 1597 ν(C=C) conjugated alkenes, 764 ν(Ar‐H) adjacent hydrogen.
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