6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde
Voriconazole (<b>VN</b>) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of <b>VN</b> have been reported in the literature. Here, we disclose a new <b>VN</b>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/1/M1603 |
| _version_ | 1797609969547214848 |
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| author | Joana L. C. Sousa Hélio M. T. Albuquerque Artur M. S. Silva |
| author_facet | Joana L. C. Sousa Hélio M. T. Albuquerque Artur M. S. Silva |
| author_sort | Joana L. C. Sousa |
| collection | DOAJ |
| description | Voriconazole (<b>VN</b>) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of <b>VN</b> have been reported in the literature. Here, we disclose a new <b>VN</b> derivative, the 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde (<b>VN-CHO</b>). This compound results from the photoredox-catalyzed hydroxymethylation of <b>VN</b>, affording a hydroxymethylated derivative (<b>VN-CH<sub>2</sub>OH</b>), followed by oxidation of the former CH<sub>2</sub>OH group. <b>VN-CHO</b> was obtained in good yield (70% yield) and its structure was unveiled by 1D (<sup>1</sup>H and <sup>13</sup>C) and 2D (HSQC and HMBC) NMR techniques. The introduction of a formyl group in <b>VN</b> structure creates a very promising site for further functionalization in a molecule which originally does not have many active sites. |
| first_indexed | 2024-03-11T06:08:53Z |
| format | Article |
| id | doaj.art-fd7983c3f1084217a0727f67fd5f8199 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:53Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-fd7983c3f1084217a0727f67fd5f81992023-11-17T12:50:01ZengMDPI AGMolbank1422-85992023-03-0120231M160310.3390/M16036-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehydeJoana L. C. Sousa0Hélio M. T. Albuquerque1Artur M. S. Silva2LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalLAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, PortugalVoriconazole (<b>VN</b>) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of <b>VN</b> have been reported in the literature. Here, we disclose a new <b>VN</b> derivative, the 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde (<b>VN-CHO</b>). This compound results from the photoredox-catalyzed hydroxymethylation of <b>VN</b>, affording a hydroxymethylated derivative (<b>VN-CH<sub>2</sub>OH</b>), followed by oxidation of the former CH<sub>2</sub>OH group. <b>VN-CHO</b> was obtained in good yield (70% yield) and its structure was unveiled by 1D (<sup>1</sup>H and <sup>13</sup>C) and 2D (HSQC and HMBC) NMR techniques. The introduction of a formyl group in <b>VN</b> structure creates a very promising site for further functionalization in a molecule which originally does not have many active sites.https://www.mdpi.com/1422-8599/2023/1/M1603voriconazolelate-stage functionalizationhydroxymethylationphotoredox reactionoxidationNMR spectroscopy |
| spellingShingle | Joana L. C. Sousa Hélio M. T. Albuquerque Artur M. S. Silva 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde Molbank voriconazole late-stage functionalization hydroxymethylation photoredox reaction oxidation NMR spectroscopy |
| title | 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
| title_full | 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
| title_fullStr | 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
| title_full_unstemmed | 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
| title_short | 6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
| title_sort | 6 2 i s i 3 i r i 3 2 4 difluorophenyl 3 hydroxy 4 1 i h i 1 2 4 triazol 1 yl butan 2 yl 5 fluoropyrimidine 4 carbaldehyde |
| topic | voriconazole late-stage functionalization hydroxymethylation photoredox reaction oxidation NMR spectroscopy |
| url | https://www.mdpi.com/1422-8599/2023/1/M1603 |
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