4120-64-3

Usage

Uses

Used in Scientific Research:
5-[1-(4-NITRO-PHENYL)-METH-(Z)-YLIDENE]-2-THIOXO-THIAZOLIDIN-4-ONE is used as a research chemical for studying its physical and chemical properties, as well as its potential interactions with other compounds. This can be crucial in advancing our understanding of complex organic molecules and their applications in various fields.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 5-[1-(4-NITRO-PHENYL)-METH-(Z)-YLIDENE]-2-THIOXO-THIAZOLIDIN-4-ONE may be utilized as a starting material or intermediate in the synthesis of new drug candidates. Its unique structure could offer novel therapeutic properties, making it a valuable component in the development of innovative medications.
Used in Chemical Synthesis:
5-[1-(4-NITRO-PHENYL)-METH-(Z)-YLIDENE]-2-THIOXO-THIAZOLIDIN-4-ONE can serve as a key component in the synthesis of other complex organic compounds. Its reactivity and structural features may enable the creation of new molecules with specific properties, which could be applied in various industries, such as materials science or specialty chemicals.
Used in Material Science:
In the field of material science, 5-[1-(4-NITRO-PHENYL)-METH-(Z)-YLIDENE]-2-THIOXO-THIAZOLIDIN-4-ONE may be explored for its potential to contribute to the development of new materials with unique properties. Its incorporation into polymers or other materials could lead to advancements in areas such as electronics, coatings, or advanced materials with specific functionalities.

InChI:InChI=1/C10H6N2O3S2/c13-9-8(17-10(16)11-9)5-6-1-3-7(4-2-6)12(14)15/h1-5H,(H,11,13,16)/b8-5+

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 2700-23-4 4-Nitrobenzylidenemalononitrile 
• 19374-88-0 5-(1-methyl-3-oxo-butylidene)-2-thioxo-thiazolidin-4-one 
• 28989-47-1 5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one 

Downstream Products

• 28996-52-3 2-methylsulfanyl-5-(4-nitro-benzylidene)-thiazol-4-one 
• 28996-47-6 3-methyl-5-(4-nitro-benzylidene)-2-thioxo-thiazolidin-4-one 
• 65562-19-8 5-(4-nitro-benzylidene)-3-(tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one 
• 104183-65-5 5-(p-Nitrobenzylidene)-3--4-oxo-thiazolidine-thione 
• 99361-26-9 (5Z)-5-(4-aminobenzylidene)-2-thioxo-1,3-thiazolidin-4-one 
• 1187463-24-6 (Z)-2'-[(5-amino-3-methyl-1-phenylpyrazol-4-yl)imino]-5'-(4-nitrobenzylidene)thiazolidin-4-one 
• 1544401-94-6 (Z)-2-(methylthio)-5-(4-nitrobenzylidene)thiazol-4(5H)-one 

Relevant academic research and scientific papers

Pharmacological characterization of the cardiovascular effect of Nibethione: ex vivo, in vivo and in silico studies

Objective: This work describes the vasorelaxant and antihypertensive effects and the mechanism of action on vascular smooth muscle cells of Nibethione, a synthetic thiazolidinedione derivative. Additionally, evidence of its cytotoxicity is assessed. Methods: Nibethione (NB) was synthesized, and its vasorelaxant effect and mechanism of action were assessed through ex vivo experiments. Molecular docking studies were used to predict the mode of interaction with L-type Ca2+ channel, and in vivo antihypertensive activity was assayed on spontaneously hypertensive rats (SHR). The cytotoxicity potential was evaluated in porcine aortic endothelial cells (PAECs) from primary explants. Key findings: Nibethione vasorelaxant effect was efficient on KCl (80?mm) and NE-contraction. This effect was deleteriously modified in the presence of potassium channel block drugs, while the maximal contraction induced with NE was significantly decreased by NB; the CaCl2-induced contraction was abolished entirely. In vivo experiments showed that NB decreased diastolic blood pressure in 20.3 percent after its administration on SHR. The molecular docking showed that NB blocks L-type Ca2+ channel, and in vitro tests showed that NB did not produce cytotoxic activity on PAECs (IC50 >1000?μm). Conclusions: Nibethione showed in vivo antihypertensive and ex vivo vasorelaxant effects with implication of voltage-dependent L-type Ca2+ channel blocking, and this may contribute to the research of novel antihypertensive drugs.

Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectra

Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative

A simple, efficient and environment-friendly procedure for the synthesis of 5-arylidene rhodanines derivatives via a Knoevenagel type reaction was developed using rhodanine, a variety of differently substituted aldehydes and Na2SO3 a

Synthesis, molecular modeling, selective aldose reductase inhibition and hypoglycemic activity of novel meglitinides

In the present study, a novel generation of selective aldose reductase ALR2 inhibitors with significant hypoglycemic activities was designed and modulated based on rhodanine scaffold joined to an acetamide linker in between two lipophilic moieties. The synthesis of the novel compounds was accomplished throughout simple chemical pathways. Molecular docking was performed on B-cell membrane protein SUR1, aldehyde reductase ALR1 and aldose reductase ALR2 active sites. Compounds 10B, 11B, 12B, 15C, 16C, 26F and 27F displayed the highest hypoglycemic activities with 80.7, 85.2, 87, 82.3, 83.5, 81.4 and 85.3% reduction in blood glucose levels, respectively. They were more potent than the standard hypoglycemic agent repaglinide with 65.4% reduction in blood glucose level. Compounds 12B and 15C with IC50 0.29 and 0.35 μM were more potent than the standard ALR2 inhibitor epalrestat with IC50 0.40 μM. They were selective towards ALR2 over ALR1 134 and 116 folds, respectively. Molecular docking studies matched with the in-vitro and in-vivo results to elucidate the dual activities of both compounds 12B and 15C as potent antagonists for ALR2 over ALR1 and good agonists for the SUR1 protein.

Green synthesis, biological activity evaluation, and molecular docking studies of aryl alkylidene 2, 4-thiazolidinedione and rhodanine derivatives as antimicrobial agents

Aims and Objective: The magic scaffolds rhodanine and thiazolidine are very important heterocyclic compounds in drug design and discovery. Those are important heterocyclic compounds that have attracted a great deal of attention due to the fact that they e

Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase

Broadened antibacterial activity was introduced to rhodanine derivatives targeting Mycobacterial tuberculosis enoyl-acyl carrier protein reductase (Mtb InhA) by recruiting feature of xacins to bring DNA Gyrase B inhibitory capability. This is significant for preventing further bacterial injections in the tuberculosis treatment. The most potent compound Cy14 suggested comparable bioactivity (IC50=3.18μM for Mtb InhA; IC50=10nM for DNA Gyrase B) with positive controls. Structure–activity relationship discussion and molecular docking model revealed the significance of rhodanine moiety and derived methoxyl on meta-position, pointing out orientations for future modification.

Discovery and development of novel rhodanine derivatives targeting enoyl-acyl carrier protein reductase

A series of rhodanine derivatives RB1–RB23 were synthesized through a two-round screening. Their Mycobacterial tuberculosis (Mtb) InhA inhibitory activity and Mtb growth blocking capability were evaluated. The most potent hit compound RB23 indicated compa

Synthesis, in-vitro cytotoxicity and antimicrobial evaluations of some novel thiazole based heterocycles

Condensation of rhodanine (1) with pyrazol-3(2H)-one derivatives (2a-f) gave 5-substituted-2-thioxo-1,3- thiazolidin-4-one derivatives (3a-f). Reaction of compound (1) with 2-arylmethylidene-malononitrile (4a-d) yielded the unexpected derivatives (5a-d). The latter compounds were subjected to cyclization reactions with malononitrile under different basic conditions, hydroxylamine hydrochloride and/or thiourea to furnish the fused thiazole derivatives (6a-d) and (8-10a-d). Coupling of (1) with diazotized aromatic amines (11a-c) in pyridine afforded the arylhydrazones (12a-c). Fusion of latter compounds with malononitrile afforded the thiazolopyridazine derivatives (13a-c). The structures of the newly synthesized compounds were elucidated via spectral data and elemental analyses. The in-vitro cytotoxic activity of compounds (3a-f) against the cell line MCF-7 was evaluated. Also, the synthesized products were investigated for their antibacterial and antifungal activities against six standard organisms including the G- bacteria, Staphylococcus aureus and Bacillus subtilis, G+ bacteria, Escherichia coli and Proteus vulgaris in addition to fungi, Candida albicans and Aspergillus flavus.

A Facial Synthesis and Anticancer Activity of (Z)-2-((5-(4-nitrobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)-substituted Acid

In order to explore the anticancer and antimicrobial activity associated with the thiazole framework, we synthesized the new series (Z)-2-((5-(4-nitrobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)amino)-substituted acid derivatives 6a–l. All the synthesized compounds were evaluated for anticancer and antimicrobial activity in vitro. Among these, the compounds 6a, 6b, 6c, 6e, 6f, 6g, 6h, 6i, 6j, and 6k showed highest antibacterial and antifungal activity. The compound 6a exhibited significant antibacterial activity against Bacillussubtilis, whereas compound 6j displays significant antifungal activity against fungal strains, that is, A.?oryzae. The in vitro anticancer studies revealed that 6e, 6g, 6h, 6k, and 6l are the most active compounds against MCF-7 and BT-474 human breast cancer cell lines, which can be regarded as the promising drug candidate for development of anticancer drugs.

Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents

Twenty novel 2-thioxo-1, 3-thiazolidin-4-one derivatives (5a-5t) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a. All the synthesized compounds were screened for their in-vitro antimycobacterial activity against MTB (H37RV, ATCC No: 27294) by Alamar Blue assay method. Compounds 5r, 5k, 5t displayed most potent in-vitro activity with MICs of 0.05, 0.1, 0.2 μg/ml concentrations respectively which are comparatively potent than the standards. Molecular docking and dynamics simulations were performed to find out the plausible mechanism of the titled compounds.