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Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles
Chemistry Department, Faculty of Science, Alexandria University, Ibrahimia P.O. Box 426, Alexandria 21321, Egypt
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Received: 18 March 2011; in revised form: 2 June 2011 / Accepted: 7 June 2011 / Published: 28 June 2011
Abstract: 2-Amino-5-(2-aryl-2H-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles 2-4 have been synthesized by the reaction of 2-aryl-2H-1,2,3-triazole-4-carboxylic acids 1 with thiosemicarbazide. Their reaction with phenacyl (p-substituted phenacyl) bromides led to formation of the respective 6-aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)imidazo[2,1-b]-1,3,4-thiadiazoles 5. Reactivity of the latter fused ring towards reaction with different electrophilic reagents afforded the corresponding 5-substituted derivatives 6-8. The structure of the above compounds was confirmed from their spectral characteristics. Some of these compounds were found to possess slight to moderate activity against the microorganisms Staphylococcus aureus, Candida albicans, Pseudomonas aeruginosa, and Escherichia coli.
Keywords: 1,3,4-thiadiazole; imidazo[2,1-b]thiadiazole; electrophile; thiosemicarbazide; phenacyl bromide; antimicrobial activity
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Atta, K.F.M.; Farahat, O.O.; Ahmed, A.Z.A.; Marei, M.G. Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles. Molecules 2011, 16, 5496-5506.
Atta KFM, Farahat OO, Ahmed AZA, Marei MG. Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles. Molecules. 2011; 16(7):5496-5506.
Atta, Kamal F. M.; Farahat, Omaima O.M.; Ahmed, Alaa Z. A.; Marei, Mohamed G. 2011. "Synthesis and Antibacterial Activities of Novel Imidazo[2,1-b]-1,3,4-thiadiazoles." Molecules 16, no. 7: 5496-5506.