Design, synthesis and evaluation of biphenyl imidazole analogues as potent antifungal agents

Zhao, Shizhen; Zhao, Liyu; Zhang, Xiangqian; Peng, Wei; Wu, Mengya; X, Su; Sun, Bin; Zhao, Dongmei; Cheng, Maosheng

doi:10.1016/j.bmcl.2019.07.037

Cited by 18 publications

(8 citation statements)

References 17 publications

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“…Zhao et al used molecular docking of two antifungal isoxazole compounds with AfCYP51B to suggest that their activity was dependent on hydrogen bond interactions between the isoxazole ring oxygen and Y122 [161]. They then focused on identifying biphenyl imidazoles with antifungal activity and used molecular modelling to suggest, despite their lack of activity against A. fumigatus, that the 2-fluorine of the biphenyl would form a hydrogen bond with the Y122 of CYP51B [162]. The same residue is conserved among fungal pathogens and is equivalent to the Y126 in Sc-CYP51 and Y118 in CaCYP51.…”

Section: Screening Techniques For Antifungal Discoverymentioning

confidence: 99%

Roles for Structural Biology in the Discovery of Drugs and Agrochemicals Targeting Sterol 14α-Demethylases

Monk

Keniya

2021

JoF

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Antifungal drugs and antifungal agrochemicals have significant limitations. These include several unintended consequences of their use including the growing importance of intrinsic and acquired resistance. These problems underpin an increasingly urgent need to improve the existing classes of antifungals and to discover novel antifungals. Structural insights into drug targets and their complexes with both substrates and inhibitory ligands increase opportunity for the discovery of more effective antifungals. Implementation of this promise, which requires multiple skill sets, is beginning to yield candidates from discovery programs that could more quickly find their place in the clinic. This review will describe how structural biology is providing information for the improvement and discovery of inhibitors targeting the essential fungal enzyme sterol 14α-demethylase.

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Section: Screening Techniques For Antifungal Discoverymentioning

confidence: 99%

Roles for Structural Biology in the Discovery of Drugs and Agrochemicals Targeting Sterol 14α-Demethylases

Monk

Keniya

2021

JoF

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“…Zhao et al [70] have synthesized biphenyl imidazole derivatives (25 a-x, 26 a-b, and 27 a-b) and evaluated the antifungal activity (Figure 20). Most of the synthesized compounds To further explore the structure activity relationships (SARs) of their previously reported antifungal lead compound 25 a, Zhao et al [71] have synthesized a series of biphenyl imidazole analogs ( 28 a-v ChemMedChem decrease in antifungal activity. Compounds bearing halogens such as À F and À Cl (28 e-f and 28 k-p) at the 2-position or 3position of the central phenyl ring, showed higher antifungal activity than those with electron-donating groups.…”

Section: Imidazolesmentioning

confidence: 99%

SAR Analysis of Heterocyclic Compounds with Monocyclic and Bicyclic Structures as Antifungal Agents

Liu

Sun

et al. 2022

ChemMedChem

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Infections caused by eukaryotic organisms, such as fungi, are generally more difficult to treat than bacterial infections. With the widespread use of antifungal drugs in humans and plants, resistance and toxicity have emerged. Therefore, it is desirable to develop new antifungal drugs with low toxicity that are not susceptible to the development of resistance. This review presents a summary of the past few years (2017-2021) of research on heterocyclic compounds as antifungal agents for use in humans and plants, focusing on the structure-activity relationships (SAR) of these compounds. This review may provide ideas and information for designing and developing new antifungal drugs with fewer side effects compared with currently available drugs.

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“…Many of the synthesized compounds had the good activity against C.albicans, C.tropicalis, C. neoformans. In addition, some compounds showed a low inhibition of various isoforms of human cytochrome P450 and had a low toxicity [9].…”

Section: Antifungal Effectmentioning

confidence: 99%

Review of pharmacological effects of imidazole derivatives

et al. 2022

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Imidazole derivatives are the perspective class of drugs with a broad spectrum of application in medicine. Imidazole is a nitrogen-containing heterocyclic ring; it has two equivalent forms; hydrogen atom may be located on any of two nitrogen atoms. Imidazole ring may interact with various cations and anions, as well as with biomolecules by different reactions; the presence of various groups in the nitrogenous heterocycle structure makes it possible to identify substances with a broad spectrum of pharmacological effects. They are very important for the production of new drugs and recently draw the special interest of scientists due to their properties in the chemistry and pharmacology. Introduction of highly active Imidazole has stimulated the significant achievements in the field of chemotherapeutic agents and plays the very important role in medicine. Therefore, the active search for highly active Imidazole compounds still continues. This article describes the antifungal and antibacterial effects identified in preclinical studies through a literature review. The purpose of this work is to review the principal effects of Imidazole published in the scientific literature in recent years.

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Design, synthesis and evaluation of biphenyl imidazole analogues as potent antifungal agents

Cited by 18 publications

References 17 publications

Roles for Structural Biology in the Discovery of Drugs and Agrochemicals Targeting Sterol 14α-Demethylases

Roles for Structural Biology in the Discovery of Drugs and Agrochemicals Targeting Sterol 14α-Demethylases

SAR Analysis of Heterocyclic Compounds with Monocyclic and Bicyclic Structures as Antifungal Agents

Review of pharmacological effects of imidazole derivatives

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