Open AccessSynthesis, Characterization, and Evaluation of Biological Activities of Imidazolyl-Isoxazoline Analogue
Author(s) -
Narayana Kudva N,
Sumana Y. Kotian,
Vrushabendra Basavanna,
Shayan Byrappa,
Srikantamurthy Ningaiah,
Turuvekere Chaitra,
Srinivasa Murthy,
K. Byrappa,
K. M. Lokanatha
Publication year - 2020
Publication title -
biointerface research in applied chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.216
H-Index - 11
ISSN - 2069-5837
DOI - 10.33263/briac106.71877197
Subject(s) - moiety , chemistry , benzaldehyde , benzimidazole , yield (engineering) , antimicrobial , combinatorial chemistry , antifungal , proton nmr , hydroxylamine , organic chemistry , alkylation , catalysis , materials science , medicine , dermatology , metallurgy
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.