Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity

Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity Publisher Pubmed

Hashemi SM¹ ; Badali H² ; Faramarzi MA³ ; Samadi N⁴ ; Afsarian MH^{2, 6} ; Irannejad H⁵ ; Emami S⁵

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1. Student Research Committee, Mazandaran University of Medical Sciences, Sari, Iran
2. Department of Medical Mycology & Parasitology/Invasive Fungi Research Center (IFRC), Mazandaran University of Medical Sciences, Sari, Iran
3. Department of Pharmaceutical Biotechnology, Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
4. Department of Drug and Food Control, Pharmaceutical Quality Assurance Research Center, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Mazandaran University of Medical Sciences, Sari, Iran
6. Departments of Microbiology, Fasa University of Medical Sciences, Fasa, Iran

Source: Molecular Diversity Published:2015

Abstract

A series of new triazole alcohol antifungals were designed by replacing one of the triazolyl moiety from fluconazole with a distinct 4-amino-3-mercapto-1,2,4-triazole motif, which is found in some antimicrobial agents. The antimicrobial susceptibility testing of target compounds demonstrated that the direct analogs of fluconazole (difluorophenethyl-triazoles) were less active against fungi, while compound 10h containing dichloro substitutions on both phenyl rings of the molecule had potent activity against yeasts including Candida albicans (four strains) and Cryptococcus neoformans (MICs = 2–8 μg/mL). Also, compound 10h was active against Candida parapsilosis, Epidermophyton floccosum, and Trichophyton mentagrophytes, while it showed no activity against Gram-positive and Gram-negative bacteria. Finally, a molecular docking study suggested that compound 10h interacts suitably with lanosterol 14α-demethylase, which is the key enzyme in ergosterol biosynthesis. © 2014, Springer International Publishing Switzerland.

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Alireza Foroumadi (1)

Style	Citing Format
MLA	Hashemi SM, et al.. "Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity." Molecular Diversity, vol. 19, no. 1, 2015, pp. 15-27.
APA	Hashemi SM, Badali H, Faramarzi MA, Samadi N, Afsarian MH, Irannejad H, Emami S (2015). Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity. Molecular Diversity, 19(1), 15-27.
Chicago	Hashemi SM, Badali H, Faramarzi MA, Samadi N, Afsarian MH, Irannejad H, Emami S. "Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity." Molecular Diversity 19, no. 1 (2015): 15-27.
Harvard	Hashemi SM et al. (2015) 'Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity', Molecular Diversity, 19(1), pp. 15-27.
Vancouver	Hashemi SM, Badali H, Faramarzi MA, Samadi N, Afsarian MH, Irannejad H, et al.. Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity. Molecular Diversity. 2015;19(1):15-27.
BibTex	@article{ author = {Hashemi SM and Badali H and Faramarzi MA and Samadi N and Afsarian MH and Irannejad H and Emami S}, title = {Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity}, journal = {Molecular Diversity}, volume = {19}, number = {1}, pages = {15-27}, year = {2015} }
RIS	TY - JOUR AU - Hashemi SM AU - Badali H AU - Faramarzi MA AU - Samadi N AU - Afsarian MH AU - Irannejad H AU - Emami S TI - Novel Triazole Alcohol Antifungals Derived From Fluconazole: Design, Synthesis, and Biological Activity JO - Molecular Diversity VL - 19 IS - 1 SP - 15 EP - 27 PY - 2015 ER -

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