Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives

Novel 2-(aryloxymethyl)aziridines and 2((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, C-13 NMR, and H-1 NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTh H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 mu g/mL) than the standard drugs ethambutol (MIC = 1.56 mu g/mL) and ciprofloxacin (MIC = 1.56 mu g/mL). (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

Novel 2-(aryloxymethyl)aziridines and 2((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were synthesized and evaluated for their antitubercular activities, showing promising results with some compounds exhibiting three-times more activity than standard drugs.