Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents

Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents

In this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute...

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Main Authors: Hossein Sadeghpour, Soghra Khabnadideh, Kamiar Zomorodian, Keyvan Pakshir, Khadijeh Hoseinpour, Nabiollah Javid, Ehsan Faghih-Mirzaei, Zahra Rezaei
Format: Article
Language:English
Published: MDPI AG 2017-07-01
Series:Molecules
Subjects:
fluconazole
synthesis
antifungal
lanosterol 14α-demethylase
docking
nitrotriazole
Online Access:https://www.mdpi.com/1420-3049/22/7/1150
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spelling doaj-fe5eaf9f89944432856476d4d53631a42020-11-25T02:31:02ZengMDPI AGMolecules1420-30492017-07-01227115010.3390/molecules22071150molecules22071150Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal AgentsHossein Sadeghpour0Soghra Khabnadideh1Kamiar Zomorodian2Keyvan Pakshir3Khadijeh Hoseinpour4Nabiollah Javid5Ehsan Faghih-Mirzaei6Zahra Rezaei7Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz 7146864685, IranDepartment of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz 7146864685, IranDepartment of Medical Mycology and Parasitology, School of Medicine, Shiraz University of Medical Sciences, Shiraz 7134845794, IranDepartment of Medical Mycology and Parasitology, School of Medicine, Shiraz University of Medical Sciences, Shiraz 7134845794, IranDepartment of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz 7146864685, IranDepartment of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz 7146864685, IranDepartment of Medicinal Chemistry, School of Pharmacy, Kerman University of Medical Sciences, Kerman 7616911319, IranDepartment of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz 7146864685, IranIn this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute, La Jolla, CA, USA). The structures of synthesized compound were confirmed by various methods including elemental and spectral (NMR, CHN, and Mass) analyses. Then antifungal activities of the synthesized compound were tested against several natural and clinical strains of fungi using a broth microdilution assay against several standard and clinical fungi. Nitrotriazole derivatives showed excellent and desirable antifungal activity against most of the tested fungi. Among the synthesized compounds, 5a–d and 5g, possessing nitrotriazole moiety, showed maximum antifungal activity, in particular against several fluconazole-resistant fungi.https://www.mdpi.com/1420-3049/22/7/1150fluconazolesynthesisantifungallanosterol 14α-demethylasedockingnitrotriazole
collection DOAJ
language English
format Article
sources DOAJ
author Hossein Sadeghpour
Soghra Khabnadideh
Kamiar Zomorodian
Keyvan Pakshir
Khadijeh Hoseinpour
Nabiollah Javid
Ehsan Faghih-Mirzaei
Zahra Rezaei
spellingShingle Hossein Sadeghpour
Soghra Khabnadideh
Kamiar Zomorodian
Keyvan Pakshir
Khadijeh Hoseinpour
Nabiollah Javid
Ehsan Faghih-Mirzaei
Zahra Rezaei
Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
Molecules
fluconazole
synthesis
antifungal
lanosterol 14α-demethylase
docking
nitrotriazole
author_facet Hossein Sadeghpour
Soghra Khabnadideh
Kamiar Zomorodian
Keyvan Pakshir
Khadijeh Hoseinpour
Nabiollah Javid
Ehsan Faghih-Mirzaei
Zahra Rezaei
author_sort Hossein Sadeghpour
title Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
title_short Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
title_full Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
title_fullStr Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
title_full_unstemmed Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents
title_sort design, synthesis, and biological activity of new triazole and nitro-triazole derivatives as antifungal agents
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2017-07-01
description In this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute, La Jolla, CA, USA). The structures of synthesized compound were confirmed by various methods including elemental and spectral (NMR, CHN, and Mass) analyses. Then antifungal activities of the synthesized compound were tested against several natural and clinical strains of fungi using a broth microdilution assay against several standard and clinical fungi. Nitrotriazole derivatives showed excellent and desirable antifungal activity against most of the tested fungi. Among the synthesized compounds, 5a–d and 5g, possessing nitrotriazole moiety, showed maximum antifungal activity, in particular against several fluconazole-resistant fungi.
topic fluconazole
synthesis
antifungal
lanosterol 14α-demethylase
docking
nitrotriazole
url https://www.mdpi.com/1420-3049/22/7/1150
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