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Diastereoselective Synthesis of Novel Spiro-Phosphacoumarins and Evaluation of Their Anti-Cancer Activity |
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| Authors: | Valeriia V. Sennikova Alena V. Zalaltdinova Yulia M. Sadykova Ayrat R. Khamatgalimov Almir S. Gazizov Alexandra D. Voloshina Anna P. Lyubina Syumbelya K. Amerhanova Julia K. Voronina Elena A. Chugunova Nurbol O. Appazov Alexander R. Burilov Michail A. Pudovik |
| Affiliation: | 1.Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova str. 8, 420088 Kazan, Russia;2.N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Ave. 31, 119991 Moscow, Russia;3.Korkyt Ata Kyzylorda State University, 29A Aiteke Bi St., Kyzylorda 120014, Kazakhstan |
| Abstract: | Herein we present the regio- and diastereoselective synthesis of novel pyrrolidine-fused spiro-dihydrophosphacoumarins via intermolecular [3 + 2] cycloaddition reaction. The presented approach is complementary to existing ones and provides an easy entry to the otherwise inaccessible derivatives. Additionally, the unprecedented pathway of the reaction of 4-hydroxycoumarin with azomethine ylides is described. The anti-cancer activity of the obtained compounds was tested in vitro, the most potent compound being 2.6-fold more active against the HuTu 80 cell line than the reference 5-fluorouracil, with a selectivity index > 32. |
| Keywords: | phosphacoumarin azomethine ylide cycloaddition anti-cancer cytotoxicity quantum chemistry |