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SYNTHESIS AND ANTITUBERCULAR EVALUATION OF CERTAIN PYRROLE DERIVATIVES

Authors: Sandhya Chinnamulagund, Ashwini S. Joshi;

SYNTHESIS AND ANTITUBERCULAR EVALUATION OF CERTAIN PYRROLE DERIVATIVES

Abstract

A series of 2-aryl-5-[4-(1H-pyrrol-1-yl)phenyl]-1,3,4-oxadiazole derivatives (VIa-g) have been synthesized in good yields. These compounds were synthesized with an approach to reduce the growing anti-tubercular resistance and to develop more potent and less side effects having antitubercular activity. The reaction of 2,5-dimethoxytetrahydro furan with 4-aminobenzoate (II) in presence of ethanol, which yields ethyl 4-pyrrol-1-yl benzoate (III). This ethyl-4-pyrrol-1-yl benzoate (III) on reaction with hydrazine hydrate produced 4-pyrrol-1-yl benzoic acid hydrazide (IV). This carbohydrazide on treatment with different substituted benzoyl chlorides gave intermediates (Va-g), which on cyclisation with P2O5 in the presence of DMF yielded of 2-aryl-5-[4-(1Hpyrrol-1-yl)phenyl]-1,3,4-oxadiazoles VI(a-g). Structure of newly synthesized pyrrole derivatives were confirmed on the basis of physicochemical and spectral data (IR, 1H-NMR, 13C-NMR and Mass spectra). All the synthesized compounds were screened for their antitubercular activity using Microplate Alamar Blue Assay (MABA) method. Compounds showed anti-tubercular activity at MIC values between 1.6 to 12.5 µg/ml, compounds VIb,VIc and VId showed highest activity of 1.6 µg/ml. Selected compounds were evaluated for anti-bacterial activity against gram positive (S. aureus) and gram negative (E. coli). Compounds showed moderate activity. Physicochemical properties of the selected compounds satisfieds with the Lipinski’s rule of 5.

Keywords

Pyrrole, Antitubercular activity, Antibacterial activity.

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selected citations
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This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
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