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
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 line were shown by N-benzylated spirodioxolanes. 5-Cloro-<i>N</i>-unsubstituted spirooxindoles exhibit antiaggregational activity exceeding the values of acetylsalicylic acid.
Authors
- Anna P. Lyubina (ORCID: https://orcid.org/0000-0002-2816-8142)
- I. P. Beletskaya (ORCID: https://orcid.org/0000-0001-9705-1434)
- Vladislav I. Korunas (ORCID: https://orcid.org/0000-0001-6809-5892)
- Irina D. Krylova (ORCID: https://orcid.org/0000-0001-8979-9135)
- Александр Владимирович Самородов (ORCID: https://orcid.org/0000-0001-9302-499X)
- K. A. Nazmieva (ORCID: https://orcid.org/0000-0001-6745-219X)
- Alexander Yu. Mitrofanov (ORCID: https://orcid.org/0000-0003-3141-3599)
- Alexandra D. Voloshina (ORCID: https://orcid.org/0000-0002-3540-8554)
- Arina V. Murashkina (ORCID: https://orcid.org/0000-0002-4288-8912)
- Andrei V. Bogdanov (ORCID: https://orcid.org/0000-0002-2483-4742)
- Е. А. Smolyarchuk (ORCID: https://orcid.org/0000-0002-2615-7167)
- Zulfiya A. Valiullina
- Kseniya A. Zavadich
Institutions
- Sechenov University (RU)
- Lomonosov Moscow State University (RU)
- Kazan Federal University (RU)
- Bashkir State Medical University (RU)
- A.E. Arbuzov Institute of Organic and Physical Chemistry (RU)
Publication Details
- Journal
- Molecules
- Published
- 2024-10-08
- DOI
- https://doi.org/10.3390/molecules29194764
- Citations
- 2
- Primary Topic
- Phosphorus compounds and reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Russian Science Foundation