13037-55-3

Basic information

• Product Name: 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one
• Synonyms: 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one;3-(4-Chlorophenyl)-2-thioxothiazolidin-4-one;N-(4-Chlorophenyl)rhodanine;USAF T-1;3-(4-Chlorophenyl)-2-thioxo-4-thiazolidinone, 95%;3-(4-chlorophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one;4-Chlorophenyl-N-rhodanine;4-Thiazolidinone, 3-(4-chlorophenyl)-2-thioxo-
• CAS NO: 13037-55-3
• Molecular Formula: C₉H₆ClNOS₂
• Molecular Weight: 243.74
• Mol File: 13037-55-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 370.1°Cat760mmHg
• Flash Point: 177.6°C
• Appearance: /
• Density: 1.2886 (rough estimate)
• Vapor Pressure: 1.13E-05mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• CAS DataBase Reference: 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one(13037-55-3)
• EPA Substance Registry System: 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one(13037-55-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13037-55-3(Hazardous Substances Data)

Usage

General Description

3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one is a chemical compound with potential use in scientific research and pharmaceutical experiments. It has a specific molecular structure, including a thiazolidin-4-one core. It includes a sulfanylidene group, which refers to the presence of a sulfur atom, and a functional group of a chlorine atom attached to a phenyl ring (4-chlorophenyl). 3-(4-chlorophenyl)-2-sulfanylidene-thiazolidin-4-one, like other thiazolidinones, can have various biological activities, making it of interest in medicinal chemistry for drug discovery and development. However, its specific properties and effects depend on the context in which it is used, and it is essential to handle it with care as with any other chemical or potential pharmaceutical agent. Information about its potential hazards or safety precautions should be obtained from a detailed material safety data sheet (MSDS).

InChI:InChI=1/C9H6ClNOS2/c10-6-1-3-7(4-2-6)11-8(12)5-14-9(11)13/h1-4H,5H2

Upstream product

• 1197-56-4 ammonium salt of N-p-chlorophenylamino dithiocarbamic acid 
• 79-08-3 bromoacetic acid 
• 106-47-8 4-chloro-aniline 
• 1197-56-4 ammonium (4-chlorophenyl)carbamodithioate 
• 1313419-72-5 C₉H₇ClNO₂S₂^(1-)*Na⁽¹⁺⁾ 
• 3926-62-3 sodium monochloroacetic acid 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 68-11-1 mercaptoacetic acid 
• 75-15-0 carbon disulfide 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 13090-94-3 5-(4-hydroxybenzylidene)-3-(4-chlorophenyl)-2-thio-4-thiazolidinone 
• 158979-76-1 3-(4-Chloro-phenyl)-5-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-2-thioxo-thiazolidin-4-one 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 4999-62-6 1-chloro-4-[(cyanocarbonothioyl)amino]benzene 
• 1198159-41-9 (Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one 
• 126751-01-7 3-(4-Chloro-phenyl)-7-(2-hydroxy-phenyl)-5-oxo-2-thioxo-2,3,4,5-tetrahydro-thiazolo[4,5-b]pyridine-6-carbonitrile 
• 126751-02-8 3-(4-Chloro-phenyl)-5-oxo-7-phenyl-2-thioxo-2,3,4,5-tetrahydro-thiazolo[4,5-b]pyridine-6-carbonitrile 
• 158980-02-0 3-(4-Chloro-phenyl)-4-hydroxy-5-{(4-methoxy-phenyl)-[5-(4-nitro-phenyl)-3H-[1,3,4]thiadiazol-(2E)-ylideneamino]-methyl}-3H-thiazole-2-thione 

Relevant articles and documents

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.

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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.