Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation.
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TLDR
An efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2-4-Triazole-benzothiazole molecular conjugates, recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.Abstract:
The present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles 4a-e through a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involves in situ generation of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates 6a-o were recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.read more
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Design, synthesis, DNA binding, modeling, anticancer studies and DFT calculations of Schiff bases tethering benzothiazole-1,2,3-triazole conjugates
Meshal A. Almehmadi,Ateyatallah Aljuhani,Shaya Y. Al-Raqa,Imran Ali,Imran Ali,Nadjet Rezki,Mohamed Reda Aouad,Mohamed Hagar,Mohamed Hagar +8 more
TL;DR: In this paper, focused thiopropargylated benzothiazole was reacted with ethyl azidoacetate and/or ethyl Azidobenzoate to yield newer 1,2,3-triazole-benzothiazoles conjugates bearing ester functionality through click chemistry approach.
Journal ArticleDOI
Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles
Mohamed Reda Aouad,Mohamed Reda Aouad,Meshal A. Almehmadi,Nadjet Rezki,Nadjet Rezki,Fawzia F. Al-blewi,Mouslim Messali,Imran Ali,Imran Ali +8 more
TL;DR: In this paper, a series of benzothiazole-1,2,3-triazoles were designed and synthesized through the click chemistry approach; the DNA binding constants (Kb) were in the range of 1.732
Journal ArticleDOI
Novel scaffold hopping of potent benzothiazole and isatin analogues linked to 1,2,3-triazole fragment that mimic quinazoline epidermal growth factor receptor inhibitors: Synthesis, antitumor and mechanistic analyses.
Nadjet Rezki,Meshal A. Almehmadi,Saleh Ihmaid,Ahmed M. Shehata,Abdelsattar M. Omar,Hany E.A. Ahmed,Hany E.A. Ahmed,Mohamed Reda Aouad +7 more
TL;DR: Novel triazole-sulpha drug hybrid for the first time as EGFR inhibitors are introduced and the results indicate that the newly discovered inhibitors have significant potential for anticancer treatment.
Journal ArticleDOI
Design, Synthesis and Anticancer Screening of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids
Mohamed Reda Aouad,Moataz A. Soliman,Muath O Alharbi,Sanaa K. Bardaweel,Pramod K. Sahu,Adeeb A. Ali,Mouslim Messali,Nadjet Rezki,Nadjet Rezki,Yaseen A. Al-Soud +9 more
TL;DR: A library of novel regioselective 1,4,5-trisubstituted-1,2,3-triazole based benzothiazole-piperazine conjugates designed and synthesized using the click synthesis approach in the presence and absence of the Cu(I) catalyst found good agreement with in vitro activity.
Journal ArticleDOI
Design, synthesis, ADME prediction and pharmacological evaluation of novel benzimidazole-1,2,3-triazole-sulfonamide hybrids as antimicrobial and antiproliferative agents.
Fawzia F. Al-blewi,Meshal A. Almehmadi,Mohamed Reda Aouad,Mohamed Reda Aouad,Sanaa K. Bardaweel,Pramod K. Sahu,Mouslim Messali,Nadjet Rezki,Nadjet Rezki,El Sayed H. El Ashry +9 more
TL;DR: The results showed that the benzimidazole-1,2,3-triazoles-sulfonamide hybrids inhibited microbial and fungal strains within MIC values from 32 to 64 μg/mL, and compound 6a emerged as the most potent antimicrobial agent.
References
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Efficient Conversion of Aromatic Amines into Azides: A One-Pot Synthesis of Triazole Linkages
TL;DR: An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described.
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Isavuconazole: A New Broad-Spectrum Triazole Antifungal Agent
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2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents.
TL;DR: One member of this series, compound 22, was selected for further evaluation in an electrophysiological model where it was found to reduce norepinephrine function in the cerebellum as measured by the NE augmentation of GABA inhibition of Purkinje neurons.
Journal ArticleDOI
1,2,3-Triazole derivatives as antitubercular agents: synthesis, biological evaluation and molecular docking study
Mubarak H. Shaikh,Dnyaneshwar D. Subhedar,Laxman Nawale,Dhiman Sarkar,Firoz A. Kalam Khan,Jaiprakash N. Sangshetti,Bapurao B. Shingate +6 more
TL;DR: Based on the results from the anti-tubercular activity, SAR for the synthesized series has been developed and this series is considered as a starting point for the development of novel and more potent anti-Tubercular agents in the future.
Journal ArticleDOI
Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports
Dinesh Kumar,Mukesh Digambar Sonawane,Brahmam Pujala,Varun Jain,Srikant Bhagat,Asit K. Chakraborti +5 more
TL;DR: In this article, the catalytic potential of various protic acids has been assessed for the one pot tandem condensation-cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones.