Design, synthesis, and evaluation of antitubercular activity of a novel benzothiazole-containing an azetidinone ring

Year 2018, Volume: 48 Issue: 2, 28 - 31, 31.08.2018

Sibaji SARKAR

Abstract

Recent studies have demonstrated that
2-amino-substituted benzothiazole derivatives exhibit significant
antitubercular activity. In this study, new compounds of
benzothiazole-containing azetidinone derivatives were designed and synthesized
using substituted benzaldehydeN-(5fluoro-1,3-benzothiazol-2-yl) semicarbazone,
chloroacetyl chloride, and  triethylamine
in DMF. The structures of the synthesized compounds were characterized by TLC,
IR, elemental analysis, and 1H NMR. In vitro screening data revealed that all
the designed and synthesized compounds A6–A10 exhibited the ability to inhibit
the growth of Mycobacterium tuberculosis in terms of MIC. Variable and modest
activity was observed against the investigated strains of bacteria; however,
the compound A6 exhibited significant antitubercular activity against M.
tuberculosis H37Rv (MTCC 200) compared to that of the reference drugs isoniazid
and rifampicin. These experimental data were consistent with our computational
predictions in terms of the compound A6 that exhibited a satisfactory backbone
for the antitubercular activity, perhaps due to an increase in hydrophobicity
resulting in better penetration through the cell wall of M. tuberculosis.

Keywords

Benzothiazole, azetidinone, Mycobacterium tuberculosis, synthesis

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