Base-Catalyzed Reaction of Isatins and (3-Hydroxyprop-1-yn-1-yl)phosphonates as a Tool for the Synthesis of Spiro-1,3-dioxolane Oxindoles with Anticancer and Anti-Platelet Properties

Murashkina, Arina V.; Bogdanov, Andrei V.; Voloshina, Alexandra D.; Lyubina, Anna P.; Samorodov, Alexandr V.; Mitrofanov, Alexander Y.; Beletskaya, Irina P.; Smolyarchuk, Elena A.; Zavadich, Kseniya A.; Valiullina, Zulfiya A.; Nazmieva, Kseniya A.; Korunas, Vladislav I.; Krylova, Irina D.

Base-Catalyzed Reaction of Isatins and (3-Hydroxyprop-1-yn-1-yl)phosphonates as a Tool for the Synthesis of Spiro-1,3-dioxolane Oxindoles with Anticancer and Anti-Platelet Properties

Murashkina, Arina V., Bogdanov, Andrei V., Voloshina, Alexandra D., Lyubina, Anna P., Samorodov, Alexandr V., Mitrofanov, Alexander Y., Beletskaya, Irina P., Smolyarchuk, Elena A., Zavadich, Kseniya A., Valiullina, Zulfiya A., Nazmieva, Kseniya A., Korunas, Vladislav I., Krylova, Irina D.

Publication date: 2024

DOI: 10.3390/molecules29194764

Abstract:

An approach to the synthesis of phosphoryl substituted spiro-1,3-dioxolane oxindoles was developed from the base-catalyzed reaction of various isatins with (3-hydroxyprop-1-yn-1-yl)phosphonates. It was found that various aryl-substituted and N-functionalized isatins with the formation of appropriate products with high yields and stereoselectivity when using t-BuOLi are able to react. Cytotoxic activity evaluation suggests that the most significant results in relation to the HuTu 80 cell line were shown by N-benzylated spirodioxolanes. 5-Cloro-N-unsubstituted spirooxindoles exhibit antiaggregational activity exceeding the values of acetylsalicylic acid. © 2024 by the authors.

Keywords:
anticoagulants, cytotoxicity, isatin, phosphonates, spiro compounds, stereoselectivity, Scopus

Издатель: Multidisciplinary Digital Publishing Institute (MDPI)

Тип: Article

Base-Catalyzed Reaction of Isatins and (3-Hydroxyprop-1-yn-1-yl)phosphonates as a Tool for the Synthesis of Spiro-1,3-dioxolane Oxindoles with Anticancer and Anti-Platelet Properties

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