Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

Sambasivarao Kotha; Gaddamedi Sreevani; Lilya U Dzhemileva; Milyausha M Yunusbaeva; Usein M Dzhemilev; Vladimir A D'yakonov

doi:10.3762/bjoc.15.269

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

Beilstein J Org Chem. 2019 Nov 18:15:2774-2781. doi: 10.3762/bjoc.15.269. eCollection 2019.

Authors

Sambasivarao Kotha¹, Gaddamedi Sreevani¹, Lilya U Dzhemileva^{2

3}, Milyausha M Yunusbaeva², Usein M Dzhemilev², Vladimir A D'yakonov²

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India.
² Laboratory of Catalytic Synthesis, Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Prospect Octyabrya, 141, 450075, Ufa, Russian Federation.
³ Department of Immunology and Human Reproductive Health Bashkir State Medical University, Lenin Street, 3, 450003, Ufa, Russian Federation.

Abstract

We report a new synthetic approach to assemble spirothiazolidinediones via a [2 + 2 + 2] cyclotrimerization reaction and the derivatives were further functionalized through DA chemistry and click reaction. Using flow cytometry, it was shown for the first time that the new benzyl alcohol derivatives of thiazolidine-2,4-dione generated here are efficient apoptosis inducers in the HeLa, Hek293, U937, Jurkat, and K562 cell lines.

Keywords: [2 + 2 + 2] cycloaddition; apoptosis; biologically active; flow cytometry; spiro thiazolidinedione.