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Rhodanine

Base Information
  • Chemical Name:Rhodanine
  • CAS No.:141-84-4
  • Deprecated CAS:38895-62-4
  • Molecular Formula:C3H3NOS2
  • Molecular Weight:133.195
  • Hs Code.:29341000
  • European Community (EC) Number:205-505-1
  • NSC Number:1899
  • UNII:7O50LKL2G8
  • DSSTox Substance ID:DTXSID4026002
  • Nikkaji Number:J5.808D
  • Wikipedia:Rhodanine
  • Wikidata:Q2741084
  • Metabolomics Workbench ID:70041
  • ChEMBL ID:CHEMBL224633
  • Mol file:141-84-4.mol
Rhodanine

Synonyms:Rhodanine

Suppliers and Price of Rhodanine
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Rhodanine
  • 10g
  • $ 195.00
  • TCI Chemical
  • Rhodanine >99.0%(T)
  • 500g
  • $ 767.00
  • TCI Chemical
  • Rhodanine >99.0%(T)
  • 25g
  • $ 39.00
  • Sigma-Aldrich
  • Rhodanine 97%
  • 100g
  • $ 127.00
  • Sigma-Aldrich
  • Rhodanine for spectrophotometric det. of gallic acid, ≥99.0%
  • 25g
  • $ 56.80
  • Sigma-Aldrich
  • Rhodanine 97%
  • 25g
  • $ 47.80
  • Medical Isotopes, Inc.
  • Rhodanine
  • 10 g
  • $ 675.00
  • Medical Isotopes, Inc.
  • Rhodanine
  • 1 g
  • $ 575.00
  • Matrix Scientific
  • 2-Thioxo-1,3-thiazolidin-4-one
  • 100g
  • $ 59.00
  • Matrix Scientific
  • 2-Thioxo-1,3-thiazolidin-4-one
  • 25g
  • $ 19.00
Total 100 raw suppliers
Chemical Property of Rhodanine
Chemical Property:
  • Appearance/Colour:light yellow to beige fine crystalline powder 
  • Vapor Pressure:0.128mmHg at 25°C 
  • Melting Point:165-169 °C(lit.) 
  • Refractive Index:1.711 
  • Boiling Point:218.2 °C at 760 mmHg 
  • PKA:pK (25°) 5.52 
  • Flash Point:85.7 °C 
  • PSA:86.49000 
  • Density:1.59 g/cm3 
  • LogP:0.46310 
  • Storage Temp.:-20°C 
  • Solubility.:methanol: soluble0.5g/10 mL, clear, colorless to greenish-yellow 
  • Water Solubility.:SOLUBLE IN HOT WATER 
  • XLogP3:0.7
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:132.96560607
  • Heavy Atom Count:7
  • Complexity:122
Purity/Quality:

99.9% *data from raw suppliers

Rhodanine *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes:Xn 
  • Statements: 22-41 
  • Safety Statements: 22-26-39 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Other Organic Compounds
  • Canonical SMILES:C1C(=O)NC(=S)S1
  • General Description Rhodanine is a heterocyclic compound with a thiazolidine core, known for its diverse biological activities, including inhibitory effects on enzymes like human arylamine N-acetyltransferase 1 (NAT1) and its murine homologue (Nat2), as well as potential antitubercular properties. It serves as a key scaffold in medicinal chemistry, particularly in the development of competitive enzyme inhibitors and antimicrobial agents, due to its ability to bind to active sites and exhibit submicromolar activity. Its derivatives, such as rhodanine-3-acetic acid, have also been explored for their therapeutic potential, demonstrating relevance in drug discovery for diseases like breast cancer and tuberculosis.
Technology Process of Rhodanine

There total 30 articles about Rhodanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
carbon disulfide; With ammonium hydroxide; In water; at 40 ℃; for 0.5h;
sodium monochloroacetic acid; In water; for 0.416667 - 0.583333h;
With hydrogenchloride; In water; at 100 - 110 ℃;
DOI:10.1007/s11243-017-0159-3
Guidance literature:
With hydrogenchloride; sodium acetate; acetic acid; In N,N-dimethyl-formamide;
Guidance literature:
With hydrogenchloride; In toluene; at 110 ℃; for 8h; Solvent; Reagent/catalyst; Temperature; Catalytic behavior;
DOI:10.1055/a-1485-5925
Refernces

Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2

10.1016/j.bmc.2008.11.032

The research focuses on the identification, synthesis, and evaluation of selective small molecule inhibitors targeting human arylamine N-acetyltransferase 1 (NAT1) and its murine homologue, mouse arylamine N-acetyltransferase 2 (Nat2), which are potential markers for breast cancer. The study involves high-throughput screening of a 5000-member compound library against a panel of five different recombinant NAT proteins, including both mammalian and non-mammalian enzymes, to identify broad-spectrum inhibitors and those with specificity for individual NAT isoforms. The most potent inhibitors, identified as rhodanine and thiazolidin-2,4-dione derivatives, exhibit submicromolar activity and competitively inhibit both recombinant proteins and human NAT1 in ZR-75 cell lysates. The experiments utilized various assay methods, including the acetylation of arylamines and hydrolysis of AcCoA, to measure enzyme activity and inhibition. Additionally, 1H NMR studies were conducted on purified mouse Nat2 to confirm the binding of inhibitors within the enzyme's active site. The research also encompassed structure-activity relationship (SAR) analysis to optimize inhibitory activity and in silico modeling to predict the binding mode of the inhibitors to the protein. The compounds were further tested for cell-based toxicity to ensure their potential as non-toxic molecular tools for probing the role of human NAT1 and mouse Nat2 in cellular contexts.

Novel imidazo[2,1-b][1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents

10.1016/j.bmcl.2012.01.052

The research is focused on the synthesis and evaluation of a new class of 2-(trifluoromethyl)-6-arylimidazo[2,1-b][1,3,4]thiadiazole derivatives as potential antitubercular agents. The researchers synthesized these compounds using both conventional and microwave-assisted methods, and evaluated their in vitro antitubercular activity against M. tuberculosis H37Rv. The chemicals that played a role in the research include 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine, various substituted α-haloaryl ketones, thiazolidine-2,4-dione, 2-thioxothiazolidin-4-one (rhodanine), and 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid (rhodanine acetic acid). The synthesized compounds were characterized by IR, NMR, mass spectra, and elemental analysis. The study found that several compounds exhibited good antitubercular activity, with some showing promising potential as lead scaffolds for the development of new anti-TB agents.

Synthesis of new azocompounds and fused pyrazolo[5,1-c][1,2,4]triazines using heterocyclic components

10.1002/jhet.1533

The study, titled "Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components," investigates the synthesis of new azocompounds and tricyclic pyrazolo[5,1-c][1,2,4]triazines using various heterocyclic components. The key chemical involved is 3-methyl-4-phenyl-1H-pyrazol-5-amine, which is diazotized to form pyrazole-3(5)-diazonium chloride. This diazonium salt undergoes azocoupling reactions with a variety of heterocyclic compounds, including barbituric acid, thiobarbituric acid, 2-hetarylpyrimidine-4,6-diones, 4-hydroxy-6-methylpyridin-2(1H)-one, 4-hydroxy-6-methyl-2H-pyran-2-one, 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester, 1,3-thiazolidine-2,4-dione, and 2-thioxo-1,3-thiazolidin-4-one. These reactions yield new pyrazolylazo derivatives and fused pyrazolo[5,1-c][1,2,4]triazines through subsequent heterocyclization processes. The study explores the synthetic potential of these heterocyclic components in azocoupling reactions, highlighting their potential applications in industrial azo dyes, analytical indicators, and bioactive compounds related to purines.

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