Synthesis, Characterization, Molecular Docking, and Anticancer Evaluation of 4‐Thiazolidinone Analogues

Abstract

Scaffolds containing one or more heteroatoms are ubiquitous in nature and are responsible for almost every biological processes in flora and fauna. The fact that heterocyclic cores have high propensity for biological targets, several nitrogen, oxygen, and sulfur‐containing heterocyclic compounds have been reported in the last few decades. One such intriguing class is 4‐thiazolidinone that exhibit diverse range of pharmacological activities. In the present study, we report synthesis, characterization, molecular docking, and anticancer evaluation of 10 new 4‐thiazolidinone analogues (5–14). One of the compounds (11) was structurally characterized using single crystal X structure. Anticancer evaluation against hepatocellular carcinoma cell line (HepG2) revealed that compound (7) was the most potent (IC50 = 75 μM) while other showed moderate to low activity (85–530 μM). To underpin the druggability and possible modes of action, drug‐likeness was determined and docking studies were carried out against β‐carbonic anhydrase receptor (PDB ID: 3IA). Attempts have also been made to establish a structure–activity relationship of the reported compounds.

Quinoline‐based thiazolidinone derivatives as potent cytotoxic and apoptosis‐inducing agents through EGFR inhibition

“…Our results agreed with previous work (Aly et al, 2020; Ding & Nguyen, 2013; Havrylyuk et al, 2012; Mushtaque et al, 2019; Sonego et al, 2020; Yurttaş & Çiftçi, 2018) of the reported history of the tested derivative of quinoline or thiazolidinone‐based derivatives as apoptosis‐inducing agents.…”

“…Over the years, many quinoline derivatives have been synthesized and reported for anticancer activity (Afzal et al, 2015; Gopaul et al, 2015; Mohamed & Abuo‐Rahma, 2020; Solomon & Lee, 2011). It has also been well established that thiazolidines are incorporated in the structure of many promising anticancer compounds (Abumelha & Saeed, 2020; Deep et al, 2016; Havrylyuk et al, 2012; Irfan et al, 2020; Mushtaque et al, 2019; Nirwan et al, 2019; Türe et al, 2020). Quinoline derivatives act actively as anticancer agents through several mechanisms such as interfering with cell migration, growth inhibition, apoptosis induction, and cytotoxicity through DNA intercalation (Jain et al, 2019).…”

4-Thiazolidinone-Bearing Hybrid Molecules in Anticancer Drug Design

“…In [ 49 ], the synthesis and study of molecules 48 and 49 ( Figure 20 ), as modified analogues of hybrids 46 and 47, was reported. The authors applied the bioisosteric replacement of the pyridine core by the substituted benzene ring for the design of novel target molecules with desirable anticancer properties.…”

Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

“…[11] Thiazolidin-4-one and its derivatives have a wide range of pharmacological activities such as anticancer [12][13][14][15][16][17] anti-inflammatory, analgesic, anticonvulsant, antimicrobial, local and spinal anesthetics, central nervous system stimulants, hypnotics, anti-HIV, antidiabetic, follicle-stimulating hormone receptor antagonist. [18][19][20][21][22] The aim of this study is to develop new and effective anticancer agents through the synthesis of thiazolidin-4-one derivatives of 4-furfuryloxy-benzohydrazide. To achieve this, 16 new compounds were synthesized and their cytotoxic effects were tested in vitro against both MCF7 human breast cancer cells and MCF10A human healthy breast tissue.…”