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Synthetic approaches and structural diversity of triazolylbutanols derived from voriconazole in the antifungal drug development

Voriconazole (VCZ) was the first approved triazole antifungal drug with 1-(1H-1,2,4-triazol-1-yl)butan-2-ol substructure. This drug showed a broad spectrum of activity, especially against yeasts and molds, and opened a new avenue toward the novel class of systemic antifungal agents. Modification of...

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Published in:European journal of medicinal chemistry 2022-03, Vol.231, p.114161-114161, Article 114161
Main Authors: Ghobadi, Elham, Saednia, Shahnaz, Emami, Saeed
Format: Article
Language:English
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Summary:Voriconazole (VCZ) was the first approved triazole antifungal drug with 1-(1H-1,2,4-triazol-1-yl)butan-2-ol substructure. This drug showed a broad spectrum of activity, especially against yeasts and molds, and opened a new avenue toward the novel class of systemic antifungal agents. Modification of 2-fluoropyrimidine in the side chain of VCZ resulted in a newer generation of triazolylbutanols including efinaconazole, albaconazole, ravuconazole, and isavuconazole with the favorable antifungal spectrum, enhanced pharmacokinetic properties, and tolerable toxicity profiles. Due to the importance of triazolylbutanols in the discovery and development of new antifungal agents, in this review we have focused on the synthetic approaches and structural diversity of triazolylbutanols derived from voriconazole. This comprehensive review provides highlighting scope for medicinal chemists for the design, synthesis and development of novel potential antifungal drugs having better activity, pharmacokinetic property and toxicity profile. [Display omitted] •Voriconazole (VCZ) was the first triazole antifungal with triazolylbutanol structure.•Newer triazolylbutanols were derived from VCZ by replacing its 2-fluoropyrimidine.•The synthetic approaches and structural diversity of triazolylbutanols have been highlighted.•Design, synthesis, SAR analysis and development of novel antifungals were discussed.•Besides drugs developed, numerous leads and drug candidates have been introduced.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2022.114161