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Molecules 2016, 21(4), 505; doi:10.3390/molecules21040505

A Green Ultrasound Synthesis, Characterization and Antibacterial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Tethering Bioactive Benzothiazole Nucleus

1
Department of Chemistry, Faculty of Sciences, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia
2
Laboratoire de Chimie & Electrochimie des Complexes Métalliques (LCECM), USTO-MB, Department of Chemistry, Faculty of Sciences, University of Sciences, and Technology Mohamed Boudiaf, B.p. 1505 El M′nouar, Oran 31000, Algeria
Academic Editor: Richard A. Bunce
Received: 11 March 2016 / Revised: 8 April 2016 / Accepted: 12 April 2016 / Published: 18 April 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [3695 KB, uploaded 18 April 2016]   |  

Abstract

The synthesis of N-(benzo[d]thiazol-2-yl)-2-(4-substituted-1H-1,2,3-triazol-1-yl)acetamides 5a–r via the 1,3-dipolar cycloaddition reaction between 2-azido-N-(benzo[d]thiazol-2-yl)acetamide derivatives 3a–c and different alkynes were performed in the presence and absence of ultrasound irradiation. The synthesis was carried out using t-BuOH/H2O (1:1, v/v) as reaction solvents and CuSO4·5H2O/sodium ascorbate as the catalyst. The copper catalyst was implemented to provide the regioselective 1,4-disubstituted 1,2,3-triazoles 5a–r. Significant reductions in reaction times with comparably higher yields were observed when the reactions were carried out under ultrasound irradiation. The structures of the newly synthesized 1,2,3-triazoles were elucidated by IR, NMR, MS, and elemental analyses. They were also screened for their antimicrobial activity against three gram-positive (Streptococcus pneumonia, Bacillus subtilis, and Staphylococcus aureus), three gram-negative (Pseudomonas aeuroginosa, Escherichia coli, and Klebsiella pneumonia), and two fungal strains (Aspergillus fumigates and Candida albicans). Most of the tested compounds displayed promising antimicrobial activities at a Minimum Inhibition Concentration (MIC) of 4–16 μg/mL. View Full-Text
Keywords: 1,2,3-triazole; benzothiazole; 1,3-dipolar cycloaddition; ultrasound; antimicrobial activity 1,2,3-triazole; benzothiazole; 1,3-dipolar cycloaddition; ultrasound; antimicrobial activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Rezki, N. A Green Ultrasound Synthesis, Characterization and Antibacterial Evaluation of 1,4-Disubstituted 1,2,3-Triazoles Tethering Bioactive Benzothiazole Nucleus. Molecules 2016, 21, 505.

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