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
Arina V. Murashkina,
Andrei V. Bogdanov,
Alexandra D. Voloshina,
Anna P. Lyubina,
Alexandr V. Samorodov,
Alexander Y. Mitrofanov,
Irina P. Beletskaya,
Elena A. Smolyarchuk,
Kseniya A. Zavadich,
Zulfiya A. Valiullina,
Kseniya A. Nazmieva,
Vladislav I. Korunas,
Irina D. Krylova
Affiliations
Arina V. Murashkina
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia
Andrei V. Bogdanov
A. M. Butlerov Institute of Chemistry, Kazan Federal University, 420008 Kazan, Russia
Alexandra D. Voloshina
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, Russia
Anna P. Lyubina
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, Russia
Alexandr V. Samorodov
Department of Pharmacology, Bashkir State Medical University, 450008 Ufa, Russia
Alexander Y. Mitrofanov
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia
Irina P. Beletskaya
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia
Elena A. Smolyarchuk
The A.P. Nelyubin Institute of Pharmacy, Sechenov First Moscow State Medical University (Sechenov University), 119571 Moscow, Russia
Kseniya A. Zavadich
The A.P. Nelyubin Institute of Pharmacy, Sechenov First Moscow State Medical University (Sechenov University), 119571 Moscow, Russia
Zulfiya A. Valiullina
Department of Pharmacology, Bashkir State Medical University, 450008 Ufa, Russia
Kseniya A. Nazmieva
Department of Pharmacology, Bashkir State Medical University, 450008 Ufa, Russia
Vladislav I. Korunas
Department of Pharmacology, Bashkir State Medical University, 450008 Ufa, Russia
Irina D. Krylova
Department of Pharmacology, Bashkir State Medical University, 450008 Ufa, Russia
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.
