Synthesis, antimicrobial activities, docking studies and computational calculations of new bis-1,4-phenylene -1H-1,2,3-triazole derivatives utilized ultrasonic energy.

ABSTRACT

In this elucidation, we studied the utility of condensation reaction between 1,4-phenylenediamine (1) with acetyl acetone (2) with hydrazine hydrate utilized ultrasonic energy in one step reaction to afford the corresponding 1,1'-(1,4-phenylenebis (5-methyl-1H-1,2,3-triazole-1,4-diyl))bis(ethan-1-one) (4) in excellent yield. The ethanol solution of bis triazole (4) and different aldehyde derivatives were sonicated at 75 °C for 2 h to afford chalcone derivatives 5a-d which were confirmed via spectral data such as FTIR, 1HNMR, 13CNMR and mass spectra. Moreover, the intermolecular cyclization of chalcone (5a) with NH2NH2 in sodium hydroxide solution to give the corresponding 4,5-dihydro-1H-pyrazol-5-yl)-1H-indole (6) using ultrasonic energy for 4 h, while the Michael addition of chalcones (5a) and (5 b) with thiourea in basic condition to afford the corresponding pyrimidine-2-thiol derivatives (7) and (9). Treatment of compound (7) with NH2NH2 to afford 1,4-bis(4-(2-hydrazineyl-6-(1H-indol-3-yl)pyrimidin-4-yl) derivatives (8). The synthesized compounds were screened against various microbial strains and displayed excellent antimicrobial potential. Additionally, the docking studies of these nine compounds were carried out with (PDB ID3t88), (PDB ID2wje), (PDB ID4ynt) and (PDB ID1tgh) which were attached with different amino acids with shortage bond length, and it was noticed that PMTS1, PMTS2 and PMTS3 were the most stable compounds with the lowest energy affinity which is compatible with biological study. Furthermore, the theoretical investigation of bis-triazole compounds were optimized via DFT/B3LYP/6-31G(d) level which showed the hyperconjugation of nitrogen atoms and elucidated their physical parameters and NBO charges and confirmed their stability and biological activity.Communicated by Ramaswamy H. Sarma.