Anti-cancer and Antimicrobial Activity, In-Silico ADME and Docking Studies of Biphenyl Pyrazoline Derivatives

Abstract

The present study deals with the multicomponent Michal addition reaction of xenyl chalcone (10-17) reacting with hydrazine hydrate in the presence of ethane carboxylic acid. It afforded new pyrazoline compounds. The propane pyrazoline derivatives (18-25) skeleton structure was confirmed by spectral studies like Fourier-Transform Infrared spectroscopy, 1H NMR, 13C NMR, and CHN analysis. The adsorption, distribution, metabolism, and excretion (ADME) properties of the synthesized molecules were investigated. The results obtained in-silico demonstrated that these molecules could be considered as orally active drug candidates due to their physical and chemical properties. The compounds (18-25) were subjected to docking prediction studies by protein (1UAG) and breast cancer protein (1OQA). While Comparing with the drug ciprofloxacin, among the series of eight compounds (18-25), compound 19, 20, and 24 have the best binding affinity score (-8.5 kcal/mol). We have selected only the compound 21 (4-Cl (electronegativity group)) compound for MTT assay of breast cancer cell line studies because it has the best binding affinity score in the binding study of the compound with 1OQA protein. Synthesized pyrazoline compound (18-25) also obeys the Lipinski rule of five and other criteria of drug-likeness properties. Among the synthesized pyrazoline compound (18-25), especially compound 21 (electronegativity group (4-Cl) has the best drug-likeness property and has a value of 7.16. Furthermore, antimicrobial activity of these compounds has been evaluated against five microbial strains, and from this result, some of the newly synthesized compounds exhibit good activity.