Computer-aided molecular design, synthesis and evaluation of antifungal activity of heterocyclic compounds

•Virtual screening techniques were applied for the identification of novel hits.•Heterocyclic compounds were synthesized and tested in vitro as antifungal agents.•Some compounds showed promising activity against seven fungal species.•Minimal inhibitory concentration (MIC) values ranged from 0.12 to...

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Bibliographic Details
Published inJournal of molecular structure Vol. 1267; p. 133573
Main Authors Oliveira, Nereu Junio Cândido, Teixeira, Iasmin Natália Santos, Fernandes, Philipe Oliveira, Veríssimo, Gabriel Corrêa, Valério, Aline Dias, Moreira, Carolina Paula de Souza, Freitas, Túlio Resende, Fonseca, Anna Clara Ventura, Sabino, Adriano de Paula, Johann, Susana, Maltarollo, Vinicius Gonçalves, de Oliveira, Renata Barbosa
Format Journal Article
LanguageEnglish
Published Elsevier B.V 05.11.2022
Subjects
Antifungals
Candida
Computational studies
Cryptococcus
Thiazolylhydrazones
Antifungals
Cryptococcus
Computational studies
Candida
Thiazolylhydrazones
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Summary:•Virtual screening techniques were applied for the identification of novel hits.•Heterocyclic compounds were synthesized and tested in vitro as antifungal agents.•Some compounds showed promising activity against seven fungal species.•Minimal inhibitory concentration (MIC) values ranged from 0.12 to 250 µM.•Results provided evidence of the importance of thiazolylhydrazone as pharmacophore. Outpatient complications for fungal infections in immunocompromised patients and the development of antimicrobial drug resistance mechanisms demonstrate the need to develop new antifungal agents. In this perspective, heterocyclic compounds namely thiazolylhydrazones, furan, tetrazole, triazole and thiadiazoline derivatives were synthesized and tested in vitro against seven clinical importance Cryptococcus and Candida species. In this study, virtual screening techniques were applied using a scaffold-hopping database, FDA approved drugs and a ZINC subset. Some of the compounds evaluated showed promising antifungal activity against C. albicans, C. glabrata, C. krusei, C. parapsilosis, C. tropicalis, C. neoformans and C. gatti, displaying minimal inhibitory concentration (MIC) values in the range of 0.12–250 µM. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2022.133573