Synthesis and in vitro biological evaluation of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives as antifungal compounds fluconazole analogues View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-03-09

AUTHORS

Armando Zambrano-Huerta, Damián David Cifuentes-Castañeda, Joanatan Bautista-Renedo, Hugo Mendieta-Zerón, Roberto Carlos Melgar-Fernández, Sergio Pavón-Romero, Macario Morales-Rodríguez, Bernardo A. Frontana-Uribe, Nelly González-Rivas, Erick Cuevas-Yañez

ABSTRACT

A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-aryl-1,3-diazidopropan-2-ol derivatives and diverse alkynes using copper catalyzed azide-alkyne cycloaddition in the key step. Most of synthesized compounds showed high activity against Candida spp. strains at a 0.04–0.5 μg/mL concentration range compared to Itraconazole and Fluconazole (MIC 2.56 and 1.28 μg/mL, respectively), which were used as reference compounds. A 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivative (R1 = F and R2 = cyclopropyl) displayed an outstanding selectivity against Candida albicans and Candida krusei (MIC = 0.0075 µg/mL). Moreover, Artemia salina bioassay on 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives revealed low toxicity in this kind of compounds. In addition, molecular docking studies suggest good binding affinity of halogen atoms in some 1-aryl-1,3-diazidopropan-2-ol derivatives to HEME group present in 14-alpha demethylase (CYP51), which might explain the high antifungal activity found in these compounds. More... »

PAGES

571-579

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00044-019-02317-5

DOI

http://dx.doi.org/10.1007/s00044-019-02317-5

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1112672564


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