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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.

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.

SUBMITTER: Murashkina AV 

PROVIDER: S-EPMC11477635 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature

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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 AV   Bogdanov Andrei V AV   Voloshina Alexandra D AD   Lyubina Anna P AP   Samorodov Alexandr V AV   Mitrofanov Alexander Y AY   Beletskaya Irina P IP   Smolyarchuk Elena A EA   Zavadich Kseniya A KA   Valiullina Zulfiya A ZA   Nazmieva Kseniya A KA   Korunas Vladislav I VI   Krylova Irina D ID  

Molecules (Basel, Switzerland) 20241008 19

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 <i>t</i>-BuOLi are able to react. Cytotoxic activity evaluation suggests that the most significant results in relation to the HuTu 80 cell l  ...[more]

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