Synthesis and In Vitro Evaluation of Some Isatin-Thiazolidinone Hybrid Analogues as Anti-Proliferative Agents

Abstract

A range of isatin-thiazolidinone hybrid analogues were synthesized and their cytotoxicity was evaluated against several cancer cell lines in vitro. The acute toxicity studies in mice models revealed that these analogues possess low systemic toxicity and are safe up to 1600mg/Kg. Among the compounds synthesized, 5-(2-nitrobenzylidene)-2-(isatin-3-azino)-thiazolidin-4-one (CI) has been shown to be the most active, highly promising compound which induced S phase arrest in cell cycle in a time dependent manner. Our initial analysis indicate that incorporation of electron withdrawing group at ortho position of the ring favors over the meta and para positions for eliciting its cytostatic effect. Overall, the in vitro biological evaluation suggests that the growth inhibitory effect of CI is promising and can be studied further.

Synthesis and Anticancer Activity of Indolin‐2‐one Derivatives Bearing the 4‐Thiazolidinone Moiety

“…Interestingly, compound 5i, possessing 5-methylindolin-2-one ring and phenyl ring without substitutions, exhibited the most potent cytotoxicity against MDA-MB-231 cancer cell line. Therefore, we tentatively concluded that the electronic influences of the substituent in the phenyl ring appear to play an important role in activity, and this behavior depends on the cancer cell lines to which they are In the present study, the coupling between indolin-2-one and 5-benzylidene-4-thiazolidinone systems led to several compounds with better anticancer activity than the previously reported analogues [15,23,24]. Two neutral conjugate systems integrated at the 4-thiazolidinone moiety may contribute to the anticancer activity of these compounds, which has already been partially confirmed by anticancer activity of the rhodacyanine dyes [25].…”

Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents

“…Several research groups adopted hybridization approach for the design of isatin-thiazolidine/thiazolidinone hybrid analogues as potent antiproliferative agents [22][23][24][25][26]. Lee and co-workers reported two studies about the design, synthesis and cytotoxicity evaluation of two different series of isatin-benzothiazole and isatin-linked chalcones analogs against three human breast cancer cell lines.…”

Allyl‐isatin suppresses cell viability, induces cell cycle arrest, and promotes cell apoptosis in hepatocellular carcinoma HepG2 cells

“…Indole compounds have recently become a hot topic in the study of antitumor drugs because of their low toxicity . ISA is a monomer of indirubin, which is an antitumor drug developed in China for the clinical treatment of chronic myelocytic leukemia .…”