Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.
Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol...
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| Format: | Article |
| Language: | English |
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Wiley
2017-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2017/5207439 |
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| author | Larissa Incerti Santos de Carvalho Dalila Junqueira Alvarenga Letícia Cruz Ferreira do Carmo Lucas Gomes de Oliveira Naiara Chaves Silva Amanda Latércia Tranches Dias Luiz Felipe Leomil Coelho Thiago Belarmino de Souza Danielle Ferreira Dias Diogo Teixeira Carvalho |
| author_facet | Larissa Incerti Santos de Carvalho Dalila Junqueira Alvarenga Letícia Cruz Ferreira do Carmo Lucas Gomes de Oliveira Naiara Chaves Silva Amanda Latércia Tranches Dias Luiz Felipe Leomil Coelho Thiago Belarmino de Souza Danielle Ferreira Dias Diogo Teixeira Carvalho |
| author_sort | Larissa Incerti Santos de Carvalho |
| collection | DOAJ |
| description | Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b′, 5c, and 5d′) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b′ and 5d′) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization. |
| format | Article |
| id | doaj-art-73bada5974674d09b1819d22695ab038 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2017-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-73bada5974674d09b1819d22695ab0382025-02-03T07:26:07ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/52074395207439Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.Larissa Incerti Santos de Carvalho0Dalila Junqueira Alvarenga1Letícia Cruz Ferreira do Carmo2Lucas Gomes de Oliveira3Naiara Chaves Silva4Amanda Latércia Tranches Dias5Luiz Felipe Leomil Coelho6Thiago Belarmino de Souza7Danielle Ferreira Dias8Diogo Teixeira Carvalho9Department of Foods and Drugs, Faculty of Pharmaceutical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Foods and Drugs, Faculty of Pharmaceutical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Foods and Drugs, Faculty of Pharmaceutical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Foods and Drugs, Faculty of Pharmaceutical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Microbiology and Immunology, Institute of Biomedical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Microbiology and Immunology, Institute of Biomedical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Microbiology and Immunology, Institute of Biomedical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilInstitute of Chemistry, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilInstitute of Chemistry, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilDepartment of Foods and Drugs, Faculty of Pharmaceutical Sciences, Federal University of Alfenas, 37130-001 Alfenas, MG, BrazilEugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b′, 5c, and 5d′) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b′ and 5d′) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.http://dx.doi.org/10.1155/2017/5207439 |
| spellingShingle | Larissa Incerti Santos de Carvalho Dalila Junqueira Alvarenga Letícia Cruz Ferreira do Carmo Lucas Gomes de Oliveira Naiara Chaves Silva Amanda Latércia Tranches Dias Luiz Felipe Leomil Coelho Thiago Belarmino de Souza Danielle Ferreira Dias Diogo Teixeira Carvalho Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. Journal of Chemistry |
| title | Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. |
| title_full | Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. |
| title_fullStr | Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. |
| title_full_unstemmed | Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. |
| title_short | Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp. |
| title_sort | antifungal activity of new eugenol benzoxazole hybrids against candida spp |
| url | http://dx.doi.org/10.1155/2017/5207439 |
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