3919-81-1

Basic information

• Product Name: 3-(p-tolyl)-rhodanin
• Synonyms: 3-(4-methylphenyl)-2-thioxo-4-thiazolidinone;3-(4-methylphenyl)rhodanine;3-(p-tolyl)-rhodanin;3-(p-tolyl)rhodanine;3-(4-Methylphenyl)-2-thioxo-1,3-thiazolidin-4-one;3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one;3-(4-methylphenyl)-2-thioxo-thiazolidin-4-one;2-Thioxo-3-(4-Methylphenyl)-4-thiazolidinone, 95%
• CAS NO: 3919-81-1
• Molecular Formula: C₁₀H₉NOS₂
• Molecular Weight: 223.31456
• Mol File: 3919-81-1.mol

Chemical Properties

• Boiling Point: 354.4 °C at 760 mmHg
• Flash Point: 168.1 °C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 3.37E-05mmHg at 25°C
• Refractive Index: 1.709
• CAS DataBase Reference: 3-(p-tolyl)-rhodanin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(p-tolyl)-rhodanin(3919-81-1)
• EPA Substance Registry System: 3-(p-tolyl)-rhodanin(3919-81-1)

Safety Data

• Hazardous Substances Data: 3919-81-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(p-tolyl)-rhodanin is used as a research compound for its potential as an antitumor agent, given its demonstrated ability to inhibit the growth of certain cancer cell lines. It is valued for its contribution to the development of new drugs for cancer treatment.
Used in Antituberculosis Drug Development:
3-(p-tolyl)-rhodanin is utilized as a key component in the research and development of new antituberculosis drugs, capitalizing on its antituberculosis properties to combat this infectious disease.
Used in Antiviral Drug Research:
3-(p-tolyl)-rhodanin is employed in antiviral drug research, leveraging its antiviral activities to explore its potential in treating viral infections and contributing to the advancement of antiviral therapies.

InChI:InChI=1/C10H9NOS2/c1-7-2-4-8(5-3-7)11-9(12)6-14-10(11)13/h2-5H,6H2,1H3

Upstream product

• 43009-17-2 4-methylphenyl dithiocarbamic acid triethylammonium 
• 215095-73-1 C₁₀H₁₀NO₂S₂^(1-)*Na⁽¹⁺⁾ 
• 75-15-0 carbon disulfide 
• 3926-62-3 sodium monochloroacetic acid 
• 106-49-0 p-toluidine 
• 622-52-6 p-methylphenylthiourea 
• 68-11-1 mercaptoacetic acid 
• 79-08-3 bromoacetic acid 
• 623-51-8 ethyl 2-sulfanylacetate 
• 540-23-8 p-toluidine hydrochloride 
• 2365-48-2 Methyl thioglycolate 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 79-11-8 chloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 75003-56-4 5-Pyridin-2-yl-2-thioxo-3-p-tolyl-thiazolidin-4-one 
• 75003-45-1 5-Quinolin-2-yl-2-thioxo-3-p-tolyl-thiazolidin-4-one 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 4955-68-4 1-[(cyanocarbonothioyl)amino]-4-methylbenzene 
• 16240-04-3 3-(4-methylphenyl)thiazolidine-2,4-dione 
• 126750-93-4 (E)-5-(4-methoxybenzylidene)-2-thioxo-3-p-tolylthiazolidin-4-one 
• 438478-03-6 (Z)-5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-2-thioxo-3-(p-tolyl)thiazolidin-4-one 
• 1621417-91-1 5-[5-(4-chlorophenyl)-3-naphthalen-2-yl-4,5-dihydropyrazol-1-ylmethylene]-2-thioxo-3-p-tolylthiazolidin-4-one 
• 1621417-90-0 5-[5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-ylmethylene]-2-thioxo-3-p-tolylthiazolidin-4-one 
• 1621417-89-7 5-[5-(4-dimethylaminophenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-2-thioxo-3-p-tolylthiazolidin-4-one 

Relevant articles and documents

Synthesis and DFT calculations of linear and nonlinear optical responses of novel 2-thioxo-3-N,(4-methylphenyl) thiazolidine-4 one

The aim of this work is to present results of both experimental and theoretical studies of 2–thioxo–3–N, (4–methylphenyl) thiazolidine–4–one. In this paper, we present the chemical synthesis of 2–thioxo–3–N, (4–methylphenyl) thiazolidine 4–one followed by spectroscopy study. The applying of 1H and 13C nuclear magnetic resonance (NMR), ultraviolet–visible (UV–vis) spectroscopy, performed its structural characterization. UV–vis measurements showed absorption between 250 and 350 nm. The optical gap energy is calculated using the Tauc method, which comes out to be around 3.91 eV. Density functional theory (DFT) computations were adopted for the geometry optimization of this compound and to evaluate their static polarizability (the mean polarizability (Formula presented.) and the polarizability anisotropy (Formula presented.)) and static first hyperpolarizability (the electric field–induced second harmonic generation (EFISHG) (Formula presented.) and the hyper–Rayleigh scattering (HRS) (Formula presented.)) using several functionals. These static electrical properties are studied in detail. An inverse relation between the first hyperpolarizability and the HOMO–LUMO gap has been obtained for the 2–thioxo–3–N, (4–methylphenyl) thiazolidine–4–one. Based on these results, we can conclude that the synthesized molecule is considered as a good candidate for optoelectronic device applications.

Synthesis, single crystal, in-silico and in-vitro assessment of the thiazolidinones

This project was aimed to check the enzyme inhibition potential of the synthesized thiazolidinones. The target compounds (1–3) were prepared according to reported method and characterized with FTIR and single-crystal X-Ray Diffraction techniques. The comp

Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one

In the present investigation, we report a combined experimental and theoretical study of (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one synthesized by the Knoevenagel condensation of rhodanine with an aromatic aldehyde in good to excellent yields. A variety of physicochemical techniques were employed for characterization of the synthesized compound including 1H and 13C nuclear magnetic resonance (NMR), scanning electron microscopy (SEM), energy dispersive X-Ray analysis (EDX) and ultraviolet–visible (UV–VIS) spectroscopy. The geometry optimization, frontier molecular orbital energies and the energy gap of the title compound in the ground state have been investigated with density functional theory (DFT) method at different functionals (B3LYP, CAM-B3LYP, M05-2X, PBE0, and ωB97X-D) in conjunction with different basis sets. We also calculate their dipole moment, linear polarizability, and first hyperpolarizability to elucidate the nonlinear optical (NLO) activity. The HOMO–LUMO energy gap obtained from the PBE0 functional agrees with the experimental data deduced from the UV–VIS measurement. The resulting compound shows a high hyper-Rayleigh scattering (HRS) first hyperpolarizability, which makes it suitable for optoelectronic and optical devices.

A New Synthesis Strategy for Rhodanine and Its Derivatives

Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N -aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical, and convenient in good yields.

Quinolinone compound and application thereof

The invention discloses a quinolinone compound containing rhodanine and similar fragments thereof and pharmaceutically acceptable salts thereof, and relates to the technical field of organic chemistry. The quinolinone compound is shown as general formula I in the specification, wherein substituent groups R1, X and R2 have meanings given in the specification. The invention also relates to application of the compound shown as the general formula I and the pharmaceutically acceptable salts thereof in preparing medicines for treating diseases caused by abnormal expression of IDO, in particular toapplication in preparing medicines for treating and/or preventing cancers.

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

Identification of novel pyrazole-rhodanine hybrid scaffolds as potent inhibitors of aldose reductase: Design, synthesis, biological evaluation and molecular docking analysis

In an effort to develop a new class of potent aldose reductase inhibitors, a series of 1,3-diarylpyrazole assimilated 3-substituted 4-oxo-2-thioxo-1,3-thiazolidines (9a-n) was designed, and synthesized in good to excellent yields by a pharmacophore integr

Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy

Different inflammatory diseases and allergic reactions are mediated by leukotrienes, which arise from the oxygenation of arachidonic acid catalyzed by 5-lipoxygenase (5-LO). One promising approach for an effective anti-leukotriene therapy is the inhibition of this key enzyme. This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Through optimization of C06, evaluation of structure-activity relationships including profound assessment of the thiazolone core and consideration of the solubility, the 5-benzyl-2-phenyl-4-hydroxythiazoles represented by 46 (ST-1829, 5-(4-chlorobenzyl)-2-p-tolylthiazol-4-ol) were developed. Compound 46 showed an improved 5-LO inhibitory activity in cell-based (ICinf50/inf values 0.141/4M) and cell-free assays (ICinf50/inf values 0.03 1/4M) as well as a prominent enhanced solubility. Furthermore, it kept its promising inhibitory potency in the presence of blood serum, excluding excessive binding to serum proteins. These facts combined with the non-cytotoxic profile mark a major step towards an effective anti-inflammatory therapy.

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.