Synthesis and Antimicrobial Evaluation of Chiral 3, 5-Diaryl-5, 6-dihydrothiazolo[ 2, 3-c][1, 2, 4]triazoles

Author(s): Pawankumar R. Tiwari, Marina E. John, Anil V. Karnik*

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 12 , 2019


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Abstract:

Disclosed herein is a general approach for the synthesis of chiral thiazolo triazoles 5a-e. An efficient 3-step synthetic strategy has been developed to obtain the fused heterocycles in good yields. The key step involves formation of a secondary carbocation under acidic condition and intramolecular attack of the nitrogen of the 1,2,4-triazolo part leads to the formation of fused bicyclic compound in a regioselective manner. A new chiral center was created during the reaction and Chiral HPLC analyses confirmed the presence of the same and the racemic nature of the synthesized compounds. Their antimicrobial activities were evaluated by broth micro-dilution method and expressed as the minimum inhibitory concentration. The preliminary bioassay results demonstrate that most of the target compounds exhibit a significantly wide spectrum activity against S. aureus and E. coli comparable to ampicillin. The efficacies of compounds against C. albicans are either more or similar compared to Griseofulvin.

Keywords: Thaizolo[2, 3-c][1, 2, 4]triazoles, chiral HPLC, antimicrobial activity, intramolecular cyclization, chirality, fused heterocycles.

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Article Details

VOLUME: 16
ISSUE: 12
Year: 2019
Published on: 08 October, 2019
Page: [978 - 982]
Pages: 5
DOI: 10.2174/1570178616666190411102818
Price: $65

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