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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

[ Vol. 15 , Issue. 7 ]

Author(s):

Kooi-Mow Sim*, Pei-Qie Chan, Xin-Lik Boo, Ker-Sin Heng, Kah-Whei Lye and Kah-Cheng Teo   Pages 575 - 582 ( 8 )

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.

Affiliation:

Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Department of Biomedical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak, Department of Biomedical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jalan Universiti, Bandar Barat, 31900 Kampar, Perak

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