Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones

Abstract

A series of novel 5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-thiazolidinones (Ciminalum–thiazolidinone hybrid molecules) have been synthesized. Anticancer activity screening toward the NCI60 cell lines panel, gastric cancer (AGS), human colon cancer (DLD-1), and breast cancer (MCF-7 and MDA-MB-231) cell lines allowed the identification of 3-{5-[(Z,2Z)-2-chloro-3-(4-nitrophenyl)-2-propenylidene]-4-oxo-2-thioxothiazolidin-3-yl}propanoic acid (2h) with the highest level of antimitotic activity with mean GI50/TGI values of 1.57/13.3 μM and a certain sensitivity profile against leukemia (MOLT-4, SR), colon cancer (SW-620), CNS cancer (SF-539), melanoma (SK-MEL-5), gastric cancer (AGS), human colon cancer (DLD-1), and breast cancers (MCF-7 and MDA-MB-231) cell lines. The hit compounds 2f, 2i, 2j, and 2h have been found to have low toxicity toward normal human blood lymphocytes and a fairly wide therapeutic range. The significant role of the 2-chloro-3-(4-nitrophenyl)prop-2-enylidene (Ciminalum) substituent in the 5 position and the substituent’s nature in the position 3 of core heterocycle in the anticancer cytotoxicity levels of 4-thiazolidinone derivatives have been established

Anticancer Profile of Rhodanines: Structure–Activity Relationship (SAR) and Molecular Targets—A Review

“…Both compound 40 and compound 41 had low toxi levels towards normal human blood lymphocytes and a broad range of therapeutic effe These data suggest that the presence of a ciminalum moiety in the C-5 position of th thioxo-4-thiazolidinone ring is a very interesting possibility for designing novel and tentially active agents, as high cytotoxicity of the tested 5-[(Z,2Z)-2-chloro-3-(4-ni phenyl)-2-propenylidene]-2-thioxo-4-thiazolidinone-3-carboxylic acids against seve cancer cell lines have been established. Buzun et al [44] designed and synthesized a series of new 5-[(Z,2Z)-2-chloro-3-(4nitrophenyl)-2-propenylidene]-thiazolidinones, which are a combination of a thiazolidinone core and a structural fragment of the ciminalum, namely(2Z)-2-chloro-3-(4-nitrophenyl) prop-2-enal. Ciminalum is an active Gram-positive and Gram-negative antimicrobial factor [45].…”

“…Figure 20. The structures of 5-arylidenerhodanine-3-carboxylic acids.Buzun et al[44] designed and synthesized a series of new 5-[(Z,2Z)-2-chloro-3 nitrophenyl)-2-propenylidene]-thiazolidinones, which are a combination of a thiaz dinone core and a structural fragment of the ciminalum, namely(2Z)-2-chloro-3-(4-ni phenyl)prop-2-enal. Ciminalum is an active Gram-positive and Gram-negative antimic bial factor[45].…”

Synthesis, Biological Evaluation and Molecular Docking Studies of 5-Indolylmethylen-4-oxo-2-thioxothiazolidine Derivatives

“…As is known, rhodanine derivatives are synthesized by several methods, in particular by dithiocarbamate, bis(carboxymethyl)trithiocarbonate (the Holmberg method), and thiocyanate [ 35 ]. The starting 3-arylrhodanines were synthesized using the Holmberg method, making it possible to obtain compounds based on arylamines in high yields and sufficient purity, avoiding the formation of thiourea impurities.…”

Discovery of Cinnamylidene Derivative of Rhodanine with High Anthelmintic Activity against Rhabditis sp.

“…Our interest is focused on rhodanine (2-sulfanylidene-1,3-thiazolidin-4-one) derivatives, which were synthesized in our laboratory and tested for their biological activities [ 9 , 10 , 11 , 12 , 13 ]. Derivatives of rhodanine show a broad spectrum of biological activities, e.g., antibacterial, antifungal, antitubercular, anticancer, antidiabetic, anti-inflammatory and antiparasitic activities [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Given the high potency of rhodanine derivatives as bioactive agents, we have evaluated cinnamylidene derivatives of rhodanine towards their anthelmintic activity.…”