Synthesis, Characterization and Antibacterial Activity of Some New 1,2,4- Triazole Schiff bases and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines

Author(s): Kooi-Mow Sim*, Pei-Qie Chan, Xin-Lik Boo, Ker-Sin Heng, Kah-Whei Lye, Kah-Cheng Teo

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 7 , 2018

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Graphical Abstract:


Background: In the present study, fourteen new 1,2,4-triazole Schiff bases and eight new 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines incorporating a pyrimidine ring were synthesized and evaluated for their antibacterial activity.

Methods: 1,2,4-Triazole Schiff bases were prepared from the condensation of 4-amino-3-mercapto-5- (2-thiomethylpyrimidyl)-1,2,4-triazole with a series of arylaldehydes in the presence of (+)-tartaric acid as catalyst. On the other hand, the reaction of 4-amino-3-mercapto-5-(2-thiomethylpyrimidyl)-1,2,4- triazole with substituted phenacyl bromides afforded the corresponding 1,2,4-triazolo[3,4-b][1,3,4]- thiadiazines.

Results: The structures of 1,2,4-triazole Schiff bases and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines were characterized by IR, NMR and mass spectral data. All the synthesized compounds were screened for their antibacterial activities using 96-well microbroth dilution assay.

Conclusion: Schiff base with p-hydroxylphenyl substituent and triazolothiadiazine containing 4- flurophenyl ring displayed moderate antibacterial activity against Pseudomonas aeruginosa at MIC 62.5 μg/ml.

Keywords: 1, 2, 4-Triazole, pyrimidine, Schiff base, triazolothiadiazine, condensation, antibacterial.

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Article Details

Year: 2018
Page: [575 - 582]
Pages: 8
DOI: 10.2174/1570178614666171129160503
Price: $65

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