3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines

Önen-Bayram, F. Esra; Buran, Kerem; Durmaz, İrem; Berk, Barkın; Cetin-Atalay, Rengül

doi:10.1039/c4md00306c

Cited by 17 publications

(6 citation statements)

References 21 publications

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“…[38][39][40] We also presented the anticarcinogenic property of an acetylenic thiazolidine, namely, the ALC67 molecule in a previous study, 29 and showed recently that 3-propionyl-thiazolidine-4-carboxylic acid ethyl esters can be classified as a family of antiproliferative compounds. 41 Given the potency of this core structure, we wanted to investigate the mutagenicity and the genotoxicity of these acetylenic thiazolidine, choosing ALC67 molecule as the reference molecule.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the mutagenic and genotoxic effects of the ALC67 thiazolidine compound in Salmonella strains and human lymphocytes in vitro

et al. 2016

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ALC67 is an N-acylated thiazolidine compound with promising anticancer activity that led to the recent discovery of a series of 3-propionyl thiazolidine-4-carboxylic acid ethyl esters as a family of novel antiproliferative agents. Since the mutagenic and genotoxic properties of marketed anticancer molecules constitute a main issue to be addressed, this study focused on the analysis of the mutagenicity, antimutagenecity, and genotoxicity of this molecule. The mutagenicity and antimutagenicity of ALC67 were evaluated by Ames test performed on Salmonella TA98 and TA100 strains. The genotoxicity of this molecule was investigated in the chromosomal aberration assay on human lymphocytes. All results revealed that the analyzed structure is not mutagenic in the two Salmonella strains tested and was not genotoxic in human lymphocytes in vitro. On the other hand, it showed a weak antimutagenic effect in these two bacterial strains. The above results indicate that after performing some more mutagenicity assays using the other recommended strains, this compound can be safely used for the development of new structures exhibiting anticancer activities.

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Section: Discussionmentioning

confidence: 99%

Evaluation of the mutagenic and genotoxic effects of the ALC67 thiazolidine compound in Salmonella strains and human lymphocytes in vitro

et al. 2016

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“…The 1,3-thiazolidin-4-one derivatives are very important core structures of many heterocyclic compounds. Thiazolidinone and its analogues have outstanding biological activity, they are reported as antiinflammatory [15], antimicrobial [16], antidiabetic [17], anticancer [18], antioxidants [19]. On the other hand, thiazole is a well-known heterocyclic aromatic compound containing sulphur and nitrogen atoms at positions 1 and 3 of its five-member ring, respectively [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Thiazolidinones and Thiazoles in Indole Series

Vanelle

Khanoussi

Benmohammed

et al. 2023

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Recent findings confirm that thiosemicarbazones and thiazoles offer a wide range of biological properties. We report here the synthesis of two series of highly functionalized thiazole-derived compounds from the reactions of various indole-derived thiosemicarbazones with diethyl acetylenedicarboxylate and 4-bromophenacyl bromide. As a result, a series of new derivatives of thiosemicarbazone, thiazolidinone, and thiazole bearing an indole moiety was synthesized and developed in good yields.

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“…Numerous heterocyclic compounds containing nitrogen, sulfur, and oxygen heteroatoms have attracted the attention of chemists over the years because of their biological properties. In particular, the thiazolidin-4-ones, a privileged pharmacophore possesses an array of biological activities including anti-inflammatory [ 9 ], antimicrobial [ 10 ], antibiofilm [ 11 ], antiparasitic [ 12 ], anticancer [ 13 ], anti-viral [ 14 ], antidiabetic [ 15 ], antiarthritic [ 16 ], FSH agonist [ 17 ], JNK stimulating phosphatase-1 (JSP-1) [ 18 ], CNS-penetrant [ 19 ], CDK1/Cyclin B inhibition [ 20 ], COX-2 inhibitor [ 21 ] and hypoglycemia [ 22 ] properties. In the last few years, Kucukguzel et al developed substituted 4-thiazolidinones and among them compounds 1 and 4 exhibited excellent antitubercular activity with 90% and 98% inhibitions at 6.25 µg/mL, respectively [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

et al. 2020

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A search for potent antitubercular agents prompted us to design and synthesize sulfamethaoxazole incorporated 4-thiazolidinone hybrids (7a–l) by using a cyclocondensation reaction between 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) resulting in good to excellent yields. All the newly synthesized 4-thiazolidinone derivatives were screened for their in vitro antitubercular activity against M. Bovis BCG and M. tuberculosis H37Ra (MTB) strains. The compounds 7d, 7g, 7i, 7k, and 7l revealed promising antimycobacterial activity against M. Bovis and MTB strains with IC90 values in the range of 0.058–0.22 and 0.43–5.31 µg/mL, respectively. The most active compounds were also evaluated for their cytotoxicity against MCF-7, HCT 116, and A549 cell lines and were found to be non-cytotoxic. Moreover, the synthesized compounds were also analyzed for ADME (absorption, distribution, metabolism, and excretion) properties and showed potential as good oral drug candidates.

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3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines

Abstract: Modification at the 2-position of the apoptosis-inducing compound ALC 67 enables tuning of its physicochemical properties.

Cited by 17 publications

References 21 publications

Evaluation of the mutagenic and genotoxic effects of the ALC67 thiazolidine compound in Salmonella strains and human lymphocytes in vitro

Evaluation of the mutagenic and genotoxic effects of the ALC67 thiazolidine compound in Salmonella strains and human lymphocytes in vitro

Synthesis of New Thiazolidinones and Thiazoles in Indole Series

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

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