57669-54-2

Basic information

• Product Name: 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
• Synonyms: 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one;2-Thioxo-3-[4-(trifluoroMethyl)phenyl]-4-thiazolidinone, 95%;2-sulfanylidene-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one;2-thioxo-3-[4-(trifluoromethyl)phenyl]thiazolidin-4-one
• CAS NO: 57669-54-2
• Molecular Formula: C₁₀H₆F₃NOS₂
• Molecular Weight: 277.29
• Mol File: 57669-54-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 341.3°Cat760mmHg
• Flash Point: 160.2°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 8.12E-05mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one(57669-54-2)
• EPA Substance Registry System: 2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one(57669-54-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 57669-54-2(Hazardous Substances Data)

Usage

General Description

2-thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one is a complex organic compound which falls under the class of thiazolidinones, which are part of a broader class of compounds known as heterocyclic compounds. These compounds contain a ring that is not exclusively composed of carbon atoms, and in this instance, the ring system is made up of sulfur, nitrogen, and carbon atoms. Structurally, it contains a trifluoromethyl group attached to a phenyl ring, providing unique chemical properties. Exact details of its usage or potential applications are not widely documented, which is typical for many specialized or newly synthetized organic compounds. However, many similar thiazolidinone compounds are known for their broad pharmacological activities.

InChI:InChI=1/C10H6F3NOS2/c11-10(12,13)6-1-3-7(4-2-6)14-8(15)5-17-9(14)16/h1-4H,5H2

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 1430796-50-1 C₈H₆F₃NS₂*C₆H₁₂N₂ 
• 1645-65-4 4-(trifluoromethyl)phenyl isothiocyanate 
• 68-11-1 mercaptoacetic acid 
• 79-08-3 bromoacetic acid 

Relevant articles and documents

Synthesis, characterization, antibacterial and antioxidant potency of nsubstituted- 2-sulfanylidene-1,3-thiazolidin-4-one derivatives and QSAR study

Background: Rhodanine is known for its potential and important role in the medicinal chemistry since its derivatives exhibit a wide range of pharmacological activities such as antibacterial, antifungal, antidiabetic, antitubercular, anti-HIV, antiparasitic, antioxidant, anticancer, antiproliferative and anthelmintic agents. Objectives: Since N-substituted rhodanine synthons are rarely commercially available, it is desirable to develop a straightforward synthetic approach for the synthesis of these key building blocks. The objective was to synthesize a series of rhodanine derivatives and to investigate their antimicrobial and antioxidant activity. Also, in order to obtain an insight into their structure-activity relationship, QSAR studies on the antioxidant activity were performed. Methods: 1H and 13C FTNMR spectra were recorded on Bruker Avance 600 MHz NMR Spectrometer, mass analysis was carried out on ESI+ mode by LC-MS/MS API 2000. 2,2-Diphenyl-1- picrylhydrazyl radical scavenging activity (% DPPH) was determined in dimethylsulfoxide (DMSO) as a solvent. The antibacterial activity was assessed against Bacillus subtilis, Staphylococcus aureus (Gram positive) and Escherichia coli, Pseudomonas aeruginosa (Gram negative) bacteria in terms of the minimum inhibitory concentrations (MICs) by a modified broth microdilution method. Results: A series of N-substituted-2-sulfanylidene-1,3-thiazolidin-4-ones were synthesized and characterized by 1H NMR, 13C NMR, FTIR, GC MS, LCMS/MS and C,H,N,S elemental analysis. Most of the synthesized compounds showed moderate to excellent antibacterial activity (MIC values from 125 μg/ml to 15.62 μg/mL) and DPPH scavenging activity (from 3.60% to 94.40%). Compound 2-thioxo-3- (4-(trifluoromethyl)-phenyl)thiazolidin-4-one showed the most potent activity against Escherichia coli (3.125 μg/mL), equivalent to antibiotic Amikacin sulphate and against Staphylococcus aureus (0.097 μg/ml), 100 times superior then antibiotic Amikacin sulphate. It has also shown a potent antioxidant activity (95% DPPH scavenging). Two best QSAR models, obtained by GETAWAY descriptor R7p+, Balabans molecular connectivity topological index and Narumi harmonic topological index (HNar), suggest that the enhanced antioxidant activity is related to the presence of pairs of atoms higher polarizability at the topological distance 7, substituted benzene ring and longer saturated aliphatic chain in N-substituents. Conclusion: A series of novel N-substituted-2-thioxothiazolidin-4-one derivatives were designed, synthesized, characterized and evaluated for their antibacterial and antioxidant activity in vitro. Majority of the compounds showed excellent antibacterial activity compared to ampicillin and few of them have an excellent activity as compared to Chloramphenicol standard antibacterial drug. The QSAR study has clarified the importance of presenting a pairs of atoms higher polarizability, such as Cl and S at the specific distance, as well as the substituted benzene ring and a long saturated aliphatic chain in N-substituents for the enhanced antioxidant activity of 2-sulfanylidene-1,3- thiazolidin-4-one derivatives.

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.