Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

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.

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

“…Anticancer activity was evaluated against 6 different cancer cell lines. Compound 330 a has shown the highest activity against U937 cells, while the acid derivative of 330 b was effective against Jurkat cells with an IC 50 value of 0.34 nM, and was the highest apoptotic agent with 95 % of late apoptosis in K562 cells [379] …”

“…Compound 330 a has shown the highest against U937 cells, while the acid derivative of 330 b was effective against Jurkat cells with an IC 50 value of 0.34 nM, and was the highest apoptotic agent with 95 % of late apoptosis in K562 cells. [379] Moreover, a selective ring-closing metathesis (RCM) of Nsubstituted-2,4-thiazolidinedione derivatives 332 bearing differ-ent olefins at position 5 has been performed using secondgeneration Grubbs catalyst (G-II) to prepare substituted azaspiro [4.4]non-7-ene-2,4-diones 333 a-c or azaspiro [4.5]dec-7-ene-2,4-diones 333 d (Scheme 119). [380] Spiro-oxindoles are represented in many biologically active natural products such as rhynchophylline, rsorhynchophylline, spirotryprostatins A and B.…”

Contemporary progress in the green synthesis of spiro-thiazolidines and their medicinal significance: a review

“…The synthesized molecules were also subjected to a molecular docking study and the ADME-Tox characteristics of produced drugs were also estimated theoretically. S. Kotha and colleagues 33 described a new synthetic method for assembling spiro-thiazolidinediones using a [2 + 2 + 2] cyclotrimerization, followed by functionalization with DA chemistry and the click reaction (Scheme 3). The novel benzyl alcohol derivatives of thiazolidine-2,4-dione were prepared and they were proved to be effective apoptosis inducers in the Hek293, HeLa, Jurkat, U937, and K562 (cancer) cell lines for the rst time using ow cytometry.…”

“…Spirothiazolidinediones were assembled by S. Kotha and researchers 33 and were evaluated for anticancer efficacy as an efficient apoptosis inducer in the cervical cancer cell line (HeLa), human embryonic kidney cell line (Hek293), human histiocytic lymphoma cell line (U937), T-cell leukemia cell line (Jurkat), and myelogenous leukemia cell line (K562). On Jurkat, K562, HEK293, HELA, A549, and U937 cell lines, anticancer activity was compared to camptothecin and etoposide.…”