55970-10-0

Upstream product

• 24044-46-0 5-(4-bromobenzylidene)-1,3-thiazolidine-2,4-dione 
• 1122-91-4 4-bromo-benzaldehyde 
• 4303-29-1 4-thioxo-2-thiazolidinone 

Relevant academic research and scientific papers

Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids

Abstract: Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(5 R, 6 S, 7 R)-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and β -aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder reaction. The stereochemistry of the cycloaddition was confirmed by NMR spectra. The antioxidant and antimicrobial activity screening identified 7 compounds (3c, 3e, 3f, 3g, 3k, 3l, 3p) with a high level of free radical scavenging (43–77% DPPH assay), and compounds with significant influence on Staphylococcus aureus, Bacillus subtilis and Candida albicans (MIC 3.13–6.25 μ g/mL), but slight effect on Escherichia coli.

Screening of spiro-substituted thiopyrano[2,3-d]thiazoles for their cytotoxic action on tumor cells

Aim. To evaluate the in vitro cytotoxicity of novel spiro-substituted thiopyrano[2,3-d]thiazoles towards tumor cells of different tissue origin. Methods. Organic synthesis; spectral methods; MTT test, statistical analysis. Results. In vitro screening of the cytotoxic activity of the 5’-carboxy-7’-aryl-1-aryl-3’,7’-dihydro-2H,2’H,5H-spiro[pyrolidin-3,6’-thiopyrano[2,3-d] thiazol]-2,2’,5-triones and N-(4-chlorophenyl)-2-[1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3- ylidene]-acetamide was performed using various cancer cell lines (Jurkat human acute T-cell leukemia cell line, MCF-7 human breast adenocarcinoma cell line, Skov3 human ovarian carcinoma cells line, SK-Mel-28 human melanoma cells line, and SW-1573 human non-smallcell lung cancer cell line). The tested compounds possessed different cytotoxic action towards the studied tumor cells. Leukemia cells appeared to be more sensitive for the studied derivatives. The cytotoxic effect of the compound 2 towards Jurkat cells was shown to be dose- and time-dependent (3, 6, 24, 48 and 72 h). This compound demonstrated the cytotoxic action towards Jurkat cells as soon as in 6 h after its addition to the cultured cells (IC50 = 66 μM), and its toxicity towards these cells was more prominent after 24 h treatment (IC50= 40 μM). Conclusions. The panel of thiopyrano[2,3-d]thiazole derivatives was synthesized and screened for their cytotoxic activity in vitro towards tumor cells of different tissue origin. The compound 2 was found to be the most active agent with selectivity for the leukemia cells. This compound inhibits growth of the human acute T-cell leukemia cells of Jurkat line (IC50 = 33.5 μM) and possesses relatively low toxicity towards the pseudo-normal mammalian cells.

Substituted thio-arylidene thiazolidinones: synthesis and structural study

The synthesis and physico-chemical properties of fourteen 4-thio-5-arylidene-thiazolidine-2-ones and eight 3-(4-bromophenacyl)-4-thio-5-arylidene-thiazolidine-2-ones are described. These products were synthetized by the aldolisation-crotonisation reaction between aromatic aldehydes and 4-thio-thiazolidine-2-one followed by N-alkylation of this substituted compounds.