Synthesis, Characterization, and Evaluation of Biological Activities of Imidazolyl-Isoxazoline Analogue

Abstract

Synthesis of isoxazoline heterocycle containing benzimidazole moiety with the highest bioactivity using substituted benzaldehyde as starting material is reported in this paper. In the beginning, the precursor benzaldehydes were treated with hydroxylamine hydrochloride to afford respective aldoximes. The resultant compound was subjected to cyclization reaction with allyl chloride in the presence of chloramine-T to afford isoxazoline key intermediate. Finally, benzimidazole was subjected to S-alkylation with isoxazoline moiety to afford the title compound with good yield. This method cultivated many advantages like; short reaction time and easy isolation. All the compounds structurally characterized by 1H NMR, 13C NMR, LCMS, IR spectral data, and elemental analysis. Besides, all the synthesized compounds were tested for their antimicrobial and antioxidant activity. The bioactivity was envisioned that the compound 5a and 5f exhibited excellent antifungal activity, which may be helpful in developing a lead to inhibit microbes.