38728-36-8Relevant academic research and scientific papers
Novel anti-melanogenic compounds, (Z)-5-(substituted benzylidene)-4-thioxothiazolidin-2-one derivatives: In vitro and in Silico Insights
Choi, Heejeong,Choi, Inkyu,Chun, Pusoon,Hong, Sojeong,Hwang, Yeji,Jeong, Yeongmu,Jinjung, Hee,Jung, Yunjin,Kim, Min-Soo,Moon, Hyung Ryong,Park, Yujin,Ryu, Il Young,Ullah, Sultan,Yoo, Jin-Wook,Yoon, In-Soo,Yun, Hwayoung
, (2021/08/30)
To confirm that the β-phenyl-α,β-unsaturated thiocarbonyl (PUSTC) scaffold, similar to the β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold, acts as a core inhibitory structure for tyrosinase, twelve (Z)-5-(substituted benzylidene)-4-thioxothiazolidin-2-
Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
Lozynskyi, Andrii,Zasidko, Viktoria,Atamanyuk, Dmytro,Kaminskyy, Danylo,Derkach, Halyna,Karpenko, Olexandr,Ogurtsov, Volodymyr,Kutsyk, Roman,Lesyk, Roman
, p. 427 - 436 (2017/05/29)
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
Zelisko,Finiuk,Shvets,Medvid, Yu. O.,Stoika,Lesyk
, p. 282 - 290 (2017/12/18)
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.
Synthesis, anticancer and antiviral activities of novel thiopyrano[2,3-d]thiazole-6-carbaldehydes
Lozynskyi, Andrii,Golota, Sergii,Zimenkovsky, Borys,Atamanyuk, Dmytro,Gzella, Andrzej,Lesyk, Roman
, p. 1245 - 1249 (2016/08/31)
Novel rel-(6R,7R)-2-oxo-7-phenyl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-6-carbaldehydes were synthesized via regio- and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with acrolein. The synthesized compou
Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds
Lozynskyi, Andrii,Zimenkovsky, Borys,Nektegayev, Ihor,Lesyk, Roman
, p. 55 - 59 (2015/02/19)
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.
A simple green synthesis of (Z)-5-arylmethylene-4-thioxothiazolidines and thiopyrano[2,3-d]thiazolidine-2-thiones in PEG-400 under catalyst-free conditions
Metwally, Nadia Hanafy
, p. 528 - 537 (2014/08/18)
An improved Knoevenagel condensation of various aromatic aldehydes with thiazolidine-2,4-dithione and with 4-thioxothiazolidin-4-one can be achieved at room temperature in polyethylene glycol-400 without catalyst to afford (Z)-5-arylmethylene-4-thioxothia
Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels-Alder reaction and related tandem processes
Zelisko, Nataliya,Atamanyuk, Dmytro,Vasylenko, Olexandr,Bryhas, Andriy,Matiychuk, Vasyl,Gzella, Andrzej,Lesyk, Roman
, p. 720 - 729 (2014/02/14)
Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54-86% yields via hetero-Diels-Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2- thiazolidinones with crotonic, prop
Microwave-assisted synthesis, antimicrobial and cytotoxic activities of some 4-thioxo-thiazolidine-2-one derivatives
Alegaon, Shankar G.,Alagawadi, Kallanagouda R.
experimental part, p. 612 - 618 (2012/05/05)
A series of (Z)-5-arylidene-4-thioxo-thiazolidine-2-ones (4a-o) were synthesized using microwave irradiation technique. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR spectral studies and elemental analysis. All compounds were evaluated for their preliminary in vitro antimicrobial and cytotoxic activities. The investigation of antimicrobial activity profile revealed that compounds 4d, 4f, 4g, and 4h exhibited marked activity against S. aureus and E. faecalis as compared with the standard while compounds 4d and 4h exhibited good antifungal activities against C. albicans, A. flavus, A. niger and C. neoformans. In preliminary MTT cytotoxicity studies, the (Z)-5- arylidene-4-thioxo-thiazolidine-2-one derivatives (4k, 4l and 4m) were found most potent. Compound 4m inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with an IC50 values of 23, 22, 20 and 20 μM, respectively.
Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3 + 2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives
Murugan, Ramalingam,Anbazhagan,Sriman Narayanan
scheme or table, p. 3272 - 3279 (2009/10/17)
The synthesis of a series of novel dispiropyrrolidines has been accomplished by 1,3-dipolar cycloaddition reaction with 5-arylidene-1,3-thiazolidine-2,4-dione and 5-arylidene-4-thioxo-1,3-thiazolidine-2-one derivatives as dipolarophiles. The structure and stereochemistry of the cycloadduct have been established by single crystal X-ray structure and spectroscopic techniques. Molecular docking studies were performed on 1FM9 protein. The synthesized compounds were screened for their antidiabetic activity on male Wistar rats.
Substituted thio-arylidene thiazolidinones: synthesis and structural study
Albuquerque,Galdino,Chantegrel,Thomasson,Pitta,Luu-Duc
, p. 201 - 205 (2007/10/03)
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.
