In this study, whole cells of marine-derived fungi were used to reduce isatin (1H-indole-2,3-dione) to dioxindole (3-hydroxyindolin-2-one) for 7 days at 32 °C. The screening showed that several strains could reduce isatin and produce the enantioenriched dioxindole. The best conversions were obtained by Cladosporium sp. CBMAI 1237 and Westerdykella sp. CBMAI 1679, however, the best enantiomeric excess was obtained only by Aspergillus sydowii CBMAI 935 (66% ee). In conclusion, marine-derived fungi show potential for asymmetric and chemoselective reduction of isatin (1H-indole-2,3-dione).
As isatinas e os 1H-1,2,3-triazóis são duas classes de compostos com grande destaque na síntese orgânica e na química medicinal uma vez que são núcleos heterociclos com elevada reatividade, que permitem a obtenção de diversos compostos com importantes propriedades biológicas. Neste artigo, a síntese de novos 5`-(4-alquil/aril-1H-1,2,3-triazóis)-isatina via reação de cicloadição 1,3-dipolar catalisada por ácido acético é descrita. Isatin and 1H-1,2,3-triazoles are two classes of compounds with great prominence in organic synthesis and medicinal chemistry as they are heterocycle nuclei with a high reactivity allowing to obtain several compounds with important biological properties. Herein, the synthesis of novel 5'-(4-alquil/aril-1H-1,2,3-triazole)-isatin via reaction of 1,3-dipolar cycloaddition catalyzed by acetic acid is reported.
This short report describes the preparation of twelve isatin derivatives, 5'-(4-alkyl/aryl-1H-1,2,3-triazoles), using 5-azido-spiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one in the presence of various alkynes under acidic conditions and ultrasound irradiation. Compared with conventional methods, yields increased to 78-98%, and reaction times decreased to 5 min. Besides time and energy saving, there was no need for purification of the product by column chromatography on silica gel, generating less waste and spent solvent.
Because of the efficiency and selectivity that some of these derivatives have shown, it can be concluded that thio-and semicarbazones constitute promising chemical scaffolds in the search for new anti-parasitic agents.
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