Synthesis and Antifungal Activity of Novel Triazole Compounds Containing Piperazine Moiety

Wang, Yanwei; Xu, Kehan; Bai, Guojing; Huang, Lei; Wu, Qiuye; Pan, Weihua; Yu, Shichong

doi:10.3390/molecules190811333

Cited by 39 publications

(20 citation statements)

References 16 publications

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“…8,9) Moreover, CYP51 has been regarded by many researchers as a target for molecular docking and widely applied in the rational design of antifungal compounds. [10][11][12][13][14][15] Studies showed that 16) the antifungal triazoles featured a core structure composed of a triazole, a halophenyl ring, while differing in the side chains. The development of triazole drugs is primarily driven through structure optimization especially of the side chains as well as structure-activity relationship (SAR) study.…”

Section: Introductionmentioning

confidence: 99%

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

et al. 2020

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Invasive fungal disease constitutes a growing health problem and development of novel antifungal drugs with high potency and selectivity are in an urgent need. In this study, a novel series of triazole derivatives containing different ester skeleton were designed and synthesized. Microdilution broth method was used to investigate antifungal activity. Significant inhibitory activity of compounds 5c, 5d, 5e, 5f, 5m and 5n was evaluated against the Candida albicans (I), Candida albicans clinical isolate (II), Candida glabrata clinical isolate (I), and Candida glabrata (II) with minimum inhibitory concentrations (MIC 80 ) values ranging from 2 to 16 µg/mL. Notably, compounds 5e and 5n showed the best inhibition against Candida albicans (II), Candida glabrata (I), and Candida glabrata (II) at the concentrations of 2 and 8 µg/mL, respectively. Molecular docking study revealed that the target compounds interacted with CYP51 mainly through hydrophobic and van der Waals interactions. The results indicated that these novel triazole derivatives could serve as promising leads for development of antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

et al. 2020

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“…On the other hand, azole system is a structural element of many drugs that have antifungal activity such as fluconazole 6, itraconazole, voriconazole and posaconazole are widely used for treatment of invasive fungal infections (IFIs) [22]. They exerted their antifungal activity by inhibition of ergosterol synthesis, a major component of fungal membrane, through blocking the P450dependent enzyme, lanosterol 14-α-demethylase (CYP 51) [22], where the azole ring bonded to the heme iron of CYP 51. Lack of ergosterol and accumulation of 14-α-demethylase lead to loss of the function of several enzymes located in membrane that result in inhibition of fungal growth and DNA replication [23].…”

Section: Introductionmentioning

confidence: 99%

“…SAR study of the different antifungal agents indicates that the triazole ring, the difluorophenyl group, and the hydroxyl group are the important pharmacophores for the antifungal activity. Development in biological and pharmacological activities against resistant fungal strains can be obtained by modification of substituents on their side chain [22]. Similarly, 1,3,4oxadiazole as a bioisoster of 1,2,4 triazole represents an important motif in medicinal chemistry, some 1,3,4-oxadiazole derivatives experienced good antifungal activity when bonded to fluoroquinolones [36 , 37].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antifungal Activity of 1,2,4-Triazole/ or 1,3,4- Oxadiazole-ciprofloxacin hybrids

Ezelarab

Hassan

Abbas

et al. 2018

Journal of advanced Biomedical and Pharmaceutical Sciences

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Due to the rapid development of fungal strains resistance, there is become great demand of newer agents that can withstand these resistant strains. This study involves design of ciprofloxacin-triazole or ciprofloxacin-oxadiazole hybrids as potential antifungal agents for the purpose of synergism. Results showed that combination of 1,2,4-triazole or its bioisoster oxadiazole with ciprofloxacin can enhance antifungal activity against Candida albicans. The triazole hybrid 11 experienced comparable antifungal activity with itroconazole (MIC = 10.23 and 11.22 µg/mL, respectively). Molecular docking study showed that hybrid 11 can bind to the active site of lanosterol 14-α-demethylase CYP 51 with reasonable docking scores.

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“…Coumarin derivatives incorporating the 1,2,3-triazole moiety showed antifungal activity [32]. Hybrids of fluconazole with 1,2,3-triazole were proved to possess satisfactory activity [33].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antifungal Activity of Novel Benzofuran-Triazole Hybrids

Liang

Tian

et al. 2016

Molecules

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Abstract:A series of novel benzofuran-triazole hybrids was designed and synthesized by click chemistry, and their structures were characterized by HRMS, FTIR and NMR. The in vitro antifungal activity of target compounds was evaluated using the microdilution broth method against five strains of pathogenic fungi. The result indicated that the target compounds exhibited moderate to satisfactory activity. Furthermore, molecular docking was performed to investigate the binding affinities and interaction modes between the target compound and N-myristoyltransferase. Based on the results, preliminary structure activity relationships (SARs) were summarized to serve as a foundation for further investigation.

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Synthesis and Antifungal Activity of Novel Triazole Compounds Containing Piperazine Moiety

Cited by 39 publications

References 16 publications

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

Design, Synthesis and Antifungal Activity of 1,2,4-Triazole/ or 1,3,4- Oxadiazole-ciprofloxacin hybrids

Design, Synthesis and Antifungal Activity of Novel Benzofuran-Triazole Hybrids

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