3-Allyl-2-(allylthio)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one: Synthesis, spectroscopic characterization, crystal structure, computational investigations, antibacterial activity and ADMET studies

Abstract

In this investigation, we successfully synthesized a novel thiohydantoin derivative, 3-allyl-2-(allylthio)-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one (AM1). The compound underwent comprehensive characterization using various analytical techniques, including FT-IR, 1H NMR, 13C NMR, HRMS-ESI and X-ray crystal structure analysis. In the crystal, the 5-membered ring is planar with the allylthio group largely coplanar with it and the other allyl group rotated well out of the plane. Quantum computational methods were used to further information on the structure of the compound. The density functional theory was applied to optimize the structure. Using the optimized structure, vibration frequencies and global index parameters were computed, UV–Vis spectrum was simulated, and NBO analysis was carried out. Furthermore, we conducted an evaluation of its antibacterial activity against three different strains. The alkylation of thiohydantoin (AM0) resulted in a heightened antibacterial activity, leading to an increase in the inhibition zone from 13.25 ± 0.35 to 14.25±0.35 mm against Rhodococcus sp GK3. Similarly, an elevation from 12.75±0.35 to 14.15±0.35 mm was noted against Rhodococcus sp GK1. Additionally, ADMET studies were conducted to explore the potential of the title compound for use as an antibacterial drug. In silico ADMET study was also performed for predicting pharmacokinetic and toxicity profile of the title compound which expressed good drug-like behavior and a non-toxic nature.