2021
DOI: 10.3390/molecules26103057
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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 mea… Show more

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Cited by 16 publications
(11 citation statements)
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“…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].…”
Section: O Hmentioning
confidence: 99%
See 1 more Smart Citation
“…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].…”
Section: O Hmentioning
confidence: 99%
“…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].…”
mentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%