4-Thiazolidines, derivatives and analogs

Комарица, И. Д.; Baranov, S. N.; Grishuk, A. P.

doi:10.1007/bf00481594

Cited by 13 publications

(6 citation statements)

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“…The starting compounds, 2,4-thiazolidinedione [21] and 4-thioxo-2-thiazolidinone [22], were obtained as described previously. 5-Arylidene-4-thioxo-2-thiazolidinones 1a-d were prepared by Knoevenagel condensation using method A or B.…”

Section: Experimental Chemistrymentioning

confidence: 99%

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Lozynskyi

Zimenkovsky

Lesyk

2015

Heterocyclic Communications

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Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compoundsAbstract: Novel rel-(5R,6S,7S)-2- oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52-70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.

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Section: Experimental Chemistrymentioning

confidence: 99%

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Lozynskyi

Zimenkovsky

Lesyk

2015

Heterocyclic Communications

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“…[19] Thus, the starting 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones 1a-b were synthesized via Knoevenagel condensation (ethanol medium in the presence of ethylendiaminediacetate). [18] The APAs were synthesized by the reaction of the corresponding aromatic aldehyde with a pyruvic acid in aqueous methanol solution.…”

Section: Resultsmentioning

confidence: 99%

“…1). The starting compounds: 2,4-thiazolidinedione [21] , 4-thioxo-2-thiazolidinone [19] were obtained according to methods described previously. 5-Ylidene-4-thioxo-2-thiazolidinones (1a-1b) were prepared by treating 4-thioxo-2-thiazolidinone with the corresponding aldehydes and refluxed for 10 min in the ethanol medium in the presence of catalytic amount of EDDA according to published procedures.…”

Section: Resultsmentioning

confidence: 99%

Arylidene Pyruvic Acids Motif in the Synthesis of New 2H,5H-Chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles via Tandem Hetero-Diels–Alder-Hemiacetal Reaction

Lozynskyi

Zimenkovsky

Gzella

2015

Synthetic Communications

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1 Arylidene pyruvic acids motif in the synthesis of new 2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles via tandem hetero-Diels-Alderhemiacetal reaction AbstractWe have developed a tandem hetero-Diels-Alder-hemiacetal reaction using arylidene pyruvic acids with 5-(ortho-hydroxybenzylidene)-substituted 4-thioxo-2-thiazolidinones, leading to 6-hydroxy-2-oxo-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano[2,3-d][1,3]thiazole-6-carboxylic acids. The stereochemistry of cycloaddition was confirmed by NMR spectra and a single crystal Xray diffraction analysis.

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“…At VACSERA (holding company for biological products and vaccines Cairo, Egypt), the enzyme inhibition, cell cycle, apoptosis, and caspase-9 were measured. Beginning materials 1 , 2a – e , and 4a – c were acquired using the procedures previously described. − …”

Section: Methodsmentioning

confidence: 99%

Novel Thiopyrano[2,3-d]thiazole-pyrazole Hybrids as Potential Nonsulfonamide Human Carbonic Anhydrase IX and XII Inhibitors: Design, Synthesis, and Biochemical Studies

Metwally

El-Desoky

2023

ACS Omega

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In recent years, molecular hybridization strategies have developed into a potent strategy for drug discovery. A series of novel thiopyrano [2,3-d]thiazoles linked to the pyrazole moiety was designed and developed as anticancer agents by a molecular hybridization. Target compounds were synthesized and characterized by spectroscopic tools as well as X-ray crystallography analysis as in the case of thiopyrano[2,3d]thiazole derivative 5a. The MTT assay was used to demonstrate the in vitro efficacy of compounds 5a−g and 7a−j on MCF-7 and HePG-2. The results showed that some cycloadducts such as bromophenyl-4-thioxo-2-thiazolidinone 3e, 4-methylphenyl derivative of thiopyrano[2,3-d]thiazole 5d, and 6substituted-thiopyrano[2,3-d]thiazoles 7e−j displayed good to excellent IC 50 in the range of 10.08 ± 1.5 to 25.95 ± 2.8 μg/mL against the MCF-7 cell line and from 7.83 ±2.1 to 13.37 ± 1.2 μg/mL against the HePG-2 cell line. To explore the enzymatic tests for isozymes hCAIX and hCAXII, the most promising eight compounds 3e, 5d, and 7e−j with IC 50 ranging from 7.83 ± 2.1 to 25.95 ± 2.8 μM were chosen. Compound 7e exhibited an IC 50 (0.067 ± 0.003 μM) similar to that of the standard drug AZA against CAIX (0.059 ± 0.003 μM)). For CAXII, the compound 7i had an IC 50 equal to 0.123 ± 0.007 μM compared to that of AZA (0.083 ± 0.005 μM). In addition, using flow cytometry, cell cycle analysis and apoptosis studies in HePG-2 were performed for the two potent anticancer and selective carbonic anhydrase agents (7e and 7i). An enzymatic assay of these two compounds against caspase-9 was also examined. Interestingly, the molecular docking studies revealed that compounds 7e and 7i successfully embedded themselves in the active pockets of the CAIX and CAXII enzymes through different interactions. Overall, the novel thiopyrano[2,3-d]thiazole-pyrazole hybrids (7e and 7i) were suggested to be potent and selective inhibitors of CAIX and CAXII.

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4-Thiazolidines, derivatives and analogs

Cited by 13 publications

References 1 publication

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds

Arylidene Pyruvic Acids Motif in the Synthesis of New 2H,5H-Chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles via Tandem Hetero-Diels–Alder-Hemiacetal Reaction

Novel Thiopyrano[2,3-d]thiazole-pyrazole Hybrids as Potential Nonsulfonamide Human Carbonic Anhydrase IX and XII Inhibitors: Design, Synthesis, and Biochemical Studies

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