5350-09-4

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one is used as a key intermediate in the synthesis of various pharmaceuticals due to its versatile chemical structure and biological activity. Its anti-inflammatory, antioxidant, and antitumor properties make it a valuable component in the development of new drugs targeting a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one is utilized as a building block for the creation of novel agrochemicals. Its potential applications include the development of pesticides and other compounds that can protect crops from pests and diseases, thereby enhancing agricultural productivity.
Used in Antioxidant Applications:
3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one is employed as an antioxidant agent for its ability to combat oxidative stress. This makes it useful in the formulation of health supplements and nutraceuticals aimed at promoting overall health and well-being by reducing the negative effects of free radicals in the body.
Used in Anti-Inflammatory and Antitumor Therapies:
3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one is used as an anti-inflammatory and antitumor agent in the development of therapeutic treatments. Its potential to modulate inflammatory responses and inhibit tumor growth makes it a candidate for use in medications targeting inflammatory diseases and various types of cancer.
Used in Treatment of Oxidative Stress-Related Diseases:
3-(4-methoxyphenyl)-2-thioxo-1,3-thiazolidin-4-one is being studied for its potential role in treating diseases associated with oxidative stress, such as diabetes and neurodegenerative disorders. Its antioxidant properties could contribute to the management and mitigation of these conditions, offering new avenues for treatment and patient care.

InChI:InChI=1/C13H20O2S/c1-2-3-9-16-11-12(14)10-15-13-7-5-4-6-8-13/h4-8,12,14H,2-3,9-11H2,1H3

Upstream product

• 75-15-0 carbon disulfide 
• 104-94-9 4-methoxy-aniline 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 3926-62-3 sodium monochloroacetic acid 
• 43009-18-3 4-methoxyphenyl dithiocarbamic acid triethylammonium 
• 79-11-8 chloroacetic acid 
• 68-11-1 mercaptoacetic acid 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 

Downstream Products

• 52494-38-9 3-(4-methoxy-phenyl)-5-(3-oxo-3H-isobenzofuran-1-ylidene)-2-thioxo-thiazolidin-4-one 
• 18331-90-3 5-(6-fluoro-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-91-4 5-(6-chloro-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-92-5 5-(6-bromo-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-94-7 5-(5,6-dichloro-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-95-8 5-(5,6-dibromo-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-96-9 5-(5,6-diiodo-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-93-6 5-(6-iodo-2-oxo-acenaphthen-1-ylidene)-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 18331-89-0 3-(4-methoxy-phenyl)-5-(2-oxo-acenaphthen-1-ylidene)-2-thioxo-thiazolidin-4-one 
• 126751-06-2 3-(4-Methoxy-phenyl)-2-thioxo-2,3-dihydro-furo[2,3-d]thiazol-6-one 
• 106515-65-5 2-(p-anisyl)-5-nitrosorhodanine 
• 245096-15-5 3-(4-methoxyphenyl)-5-cinnamylidenerhodanine 
• 158979-75-0 5-[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 
• 158979-74-9 5-[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-3-(4-methoxy-phenyl)-2-thioxo-thiazolidin-4-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors

Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.

Synthesis and supramolecular self-assembly of thioxothiazolidinone derivatives driven by H-bonding and diverse π–hole interactions: A combined experimental and theoretical analysis

Two new 3-aryl-5-(4-nitrobenzylidene)-2-thioxothiazolidin-4-one derivatives (1 & 2) were synthesized by the Knoevenagel condensation reaction of 3-(4-aryl)-2-thioxo-1,3-thiazolidin-4-ones with 4-nitrobenzaldehyde. Both products were isolated as orange cry

Unexpected Synthesis of 2,3,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence

Bis adducts derived from a double Michael addition of rhodanine to an azo-ene system of two molecules of 1,2-diaza-1,3-dienes (DDs) have furnished the corresponding 2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.

Methods of Making and Using Thioxothiazolidine and Rhodanine Derivatives as HIV-1 and JSP-1 Inhibitors

The present invention provides methods of making and using 5-(2-(indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one derivatives having HIV-1 or JSP-1 inhibitory activity.

Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

Aqueous microwave-assisted one-pot synthesis of N-substituted rhodanines

Two aqueous, one-pot, microwave-assisted methods for the rapid synthesis of N-substituted rhodanines from amine substrates are described. Alkyl- and benzylamines could be converted into the corresponding rhodanines with an atom-efficient one-pot, three-step protocol based on carbon disulfide and chloroacetic acid in short reaction times and good to excellent yields. An alternative, microwave-assisted one-pot, one-step protocol using bis(carboxymethyl)trithiocarbonate in water was developed for the synthesis of N-arylrhodanines from anilines.

Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors

We have previously reported the discovery of a new class of potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) derived from benzylidene oxazolidinedione and thiazolidinedione scaffolds. In this study, these analogs were designed, synthesized, and evaluated in a human cell-based assay. The detailed structure-activity relationship (SAR) surrounding this pharmacophore were developed, and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg, 16 showed approximately two times more potent testosterone (T)-lowering effect against a positive control in the luteinizing hormone-releasing hormone (LH-RH)-induced T production assay. The T-lowering effect continued at ca 10% level of control over 4 h after administration. The nonsteroidal molecules based on this series have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer.

An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors

(Z)-5-(2-(1H-Indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4- one (7a-q) derivatives have been synthesized by the condensation reaction of 3-phenyl-2-thioxothiazolidin-4-ones (3a-h) with suitably substituted 2-(1H-indol-3-yl)-2-oxoacetaldehyde (6a-d) under microwave condition. The thioxothiazolidine-4-ones were prepared from the corresponding aromatic amines (1a-e) and di-(carboxymethyl)-trithiocarbonyl (2). The aldehydes (6a-h) were synthesized from the corresponding acid chlorides (5a-d) using HSnBu 3.

Design, synthesis and biological evaluation of 3-substituted 2,5-dimethyl-N-(3-(1H-tetrazol-5-yl)phenyl)pyrroles as novel potential HIV-1 gp41 inhibitors

Based on the structure of HIV-1 gp41 binding site for small-molecule inhibitors, optimization of lead 2 resulted in the discovery of a new series of 2,5-dimethyl-3-(5-(N-phenylrhodaninyl)methylene)-N-(3-(1H-tetrazol-5-yl)phenyl) pyrrole compounds with improved anti-HIV-1 activity. The most active compounds 13a and 13j exhibited significant potency against gp41 6-HB formation with IC50 values of 4.4 and 4.6 μM and against HIV-1 replication in the MT-2 cells with EC50 values of 3.2 and 2.2 μM, respectively, thus providing a new starting point to develop highly potent small-molecule HIV fusion inhibitors targeting gp41.

Structural and characterization of novel copper(II) azodye complexes

The synthetic methods of novel Cu(II) and adduct complexes, with selective azodyes containing nitrogen and oxygen donor ligands have been developed, characterized and presented. The prepared complexes fall into the stoichiometric formulae of [Cu(Ln/