Please use this identifier to cite or link to this item:
http://hdl.handle.net/10773/41860
Title: | 6-[(2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde |
Author: | Sousa, Joana L. C. Albuquerque, Hélio M. T. Silva, Artur M. S. |
Keywords: | Voriconazole Late-stage functionalization Hydroxymethylation Photoredox reaction Oxidation NMR spectroscopy |
Issue Date: | Mar-2023 |
Publisher: | MDPI |
Abstract: | Voriconazole (VN) is an antifungal drug indicated for the treatment of several fungal infections. Due to its side effects, some works involving late-stage functionalization of VN have been reported in the literature. Here, we disclose a new VN derivative, the 6-[(2S,3R)-3-(2,4-difluorophenyl)- 3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde (VNCHO). This compound results from the photoredox-catalyzed hydroxymethylation of VN, affording a hydroxymethylated derivative (VN-CH2OH), followed by oxidation of the former CH2OH group. VN-CHO was obtained in good yield (70% yield) and its structure was unveiled by 1D (1H and 13C) and 2D (HSQC and HMBC) NMR techniques. The introduction of a formyl group in VN structure creates a very promising site for further functionalization in a molecule which originally does not have many active sites. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/41860 |
DOI: | 10.3390/M1603 |
Appears in Collections: | DQ - Artigos REQUIMTE - Artigos |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Molbank 2023, 2023, M1603.pdf | 1.12 MB | Adobe PDF | View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.