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Diethyl (5-Benzyl-2-(4-(<i>N</i>′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate
oleh: Oscar Leonardo Avendaño Leon, Christophe Curti, Fabiana Maia Santos Urbancg Moncorvo, Youssef Kabri, Sébastien Redon, Eduardo Caio Torres-Santos, Romain Paoli-Lombardo, Patrice Vanelle
Format: | Article |
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Diterbitkan: | MDPI AG 2023-10-01 |
Deskripsi
As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(<i>N</i>′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote form of <i>Leishmania amazonensis</i>. Compounds containing both amidoxime and phosphonyl functional groups in dihydrofuran scaffolds are relatively rare, despite the extensive study of this heterocycle in various biological applications. Therefore, this work makes a valuable contribution to the fight against <i>Leishmania</i> spp. as a neglected disease. The cyclized 4,5-dihydrofuran intermediate scaffold was obtained via a three-step synthetic route that had previously been developed for accessing other derivatives, including the sulfone moiety. This synthesis was performed using a manganese-based free radical oxidative method under microwave irradiation. The intermediary 4,5-dihydrofuran, which included a nitrile group, tolerated the subsequent reaction with hydroxylamine hydrochloride, resulting in the formation of the target product. The target compound showed moderate activity in vitro against the promastigote form of <i>L. amazonensis</i> (IC<sub>50</sub> = 91.1 µM).