Design, synthesis and antitrypanosomal activity of heteroaryl-based 1,2,4-triazole and 1,3,4-oxadiazole derivatives

Shaykoon, Montaser Sh. A.; Marzouk, Adel A.; Soltan, Osama M.; Wanas, Amira S.; Radwan, Mohamed M.; Gouda, Ahmed M.; Youssif, Bahaa G.M.; Abdel‐Aziz, Mohamed

doi:10.1016/j.bioorg.2020.103933

Cited by 33 publications

(23 citation statements)

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“…Continuing our quest to find a compound with improved antimicrobial properties [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], the current study describes the synthesis and structure elucidation of Fluoroquinolone(ciprofloxacin)-based hybrids containing various heterocycle derivatives, as well as antimicrobial activity evaluation using various strains of Gram-positive ( S. aureus and B. subtilis ), Gram-negative ( E. coli and P. aeruginosa ), and fungi ( A. flavus and C. albicans ). In addition, the inhibitory activity of the most active compounds against E. coli DNA gyrase and topoisomerase IV has been identified as a potential molecular target.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

et al. 2021

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A novel series of ciprofloxacin hybrids comprising various heterocycle derivatives has been synthesized and structurally elucidated using 1H NMR, 13C NMR, and elementary analyses. Using ciprofloxacin as a reference, compounds 1–21 were screened in vitro against Gram-positive bacterial strains such as Staphylococcus aureus and Bacillus subtilis and Gram-negative strains such as Escherichia coli and Pseudomonas aeruginosa. As a result, many of the compounds examined had antibacterial activity equivalent to ciprofloxacin against test bacteria. Compounds 2–6, oxadiazole derivatives, were found to have antibacterial activity that was 88 to 120% that of ciprofloxacin against Gram-positive and Gram-negative bacteria. The findings showed that none of the compounds tested had antifungal activity against Aspergillus flavus, but did have poor activity against Candida albicans, ranging from 23% to 33% of fluconazole, with compound 3 being the most active (33% of fluconazole). The most potent compounds, 3, 4, 5, and 6, displayed an IC50 of 86, 42, 92, and 180 nM against E. coli DNA gyrase, respectively (novobiocin, IC50 = 170 nM). Compounds 4, 5, and 6 showed IC50 values (1.47, 6.80, and 8.92 µM, respectively) against E. coli topo IV in comparison to novobiocin (IC50 = 11 µM).

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

et al. 2021

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“…Triazole derivatives showed greater activity, but among the compounds with 1,3,4-oxadiazole, the most active derivative against T. brucei was 62 (Figure 21) (IC50 = 3.94 µM). It was stronger than α-difluoromethylornithine (DFMO) which was used as a control (IC50 = 6.1 µM) [97].…”

Section: Antitrypanocidal Activity Of 134-oxadiazole Derivativesmentioning

confidence: 99%

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

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2021

IJMS

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The worldwide development of antimicrobial resistance forces scientists to search for new compounds to which microbes would be sensitive. Many new structures contain the 1,3,4-oxadiazole ring, which have shown various antimicrobial activity, e.g., antibacterial, antitubercular, antifungal, antiprotozoal and antiviral. In many publications, the activity of new compounds exceeds the activity of already known antibiotics and other antimicrobial agents, so their potential as new drugs is very promising. The review of active antimicrobial 1,3,4-oxadiazole derivatives is based on the literature from 2015 to 2021.

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“…Pyrazole is an interesting heterocycle to investigate. It has also gotten a lot of interest because it is being studied for a broad-spectrum biological property. − The 1,3,4-oxadiazole is being studied because of its potentially relevant pharmacological activity. − …”

Section: Introductionmentioning

confidence: 99%

Conventional and Microwave-Assisted Synthesis, Antitubercular Activity, and Molecular Docking Studies of Pyrazole and Oxadiazole Hybrids

et al. 2021

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Microwave-assisted organic reaction enhancement (MORE) has become more important in synthetic organic chemistry for efficient resource utilization. In this study, we synthesized bioactive compounds using both traditional and microwave methods. Microwave-assisted synthesis takes less time and produces higher yields and quality than conventional approaches. We reported the synthesis of N′-(1-(2-(3-(4chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazol-3(2H)yl)ethylidene) substituted hydrazides (4a−t). We also tested them against two strains: M. tuberculosis H 37 Ra and M. bovis BCG. Against M. tuberculosis H 37 Ra, the compounds 4e, 4h, 4k, 4p, and 4s were the most effective. Compounds 4f, 4g, and 4s showed significant activity against M. bovis BCG. The structures of newly synthesized molecules were determined using spectral methods. Furthermore, molecular docking investigations into the active site of mycobacterial InhA yielded well-clustered solutions for these compounds' binding modalities producing a binding affinity in the range of −10.366 to −8.037. Theoretical results were in good accord with the observed experimental values. The docking score of compound 4e was −10.366, and the Glide energy was −66.459 kcal/mol.

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Design, synthesis and antitrypanosomal activity of heteroaryl-based 1,2,4-triazole and 1,3,4-oxadiazole derivatives

Cited by 33 publications

References 46 publications

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors

Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives

Conventional and Microwave-Assisted Synthesis, Antitubercular Activity, and Molecular Docking Studies of Pyrazole and Oxadiazole Hybrids

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