3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitor.

Indolizines and pyrazolo[1,5-a]pyridines were prepared via [3 + 2]-cycloaddition of pyridinium ylides to 1-chloro-2-nitrostyrenes. The synthesized molecules were evaluated for antiproliferative activities against a BE(2)-C neuroblastoma cell line with several compounds decreasing the viability of cancer cells. Indolizine 9db showed higher potency than that of all-trans-retinoic acid, an approved cancer drug. Mechanistically, it was found to inhibit tubulin polymerization and it is thus proposed that the discovered chemistry can be exploited for the development of novel microtubule-targeting anticancer agents.

Citation

Alexander V Aksenov, Nikolai A Arutiunov, Nikita K Kirilov, Dmitrii A Aksenov, Igor Yu Grishin, Nicolai A Aksenov, Huifen Wang, Liqin Du, Tania Betancourt, Stephen C Pelly, Alexander Kornienko, Michael Rubin. 3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitor. Organic & biomolecular chemistry. 2021 Sep 07;19(33):7234-7245

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PMID: 34387294

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