118192
Rhodanine
97%
Synonym(s):
2-Thioxo-4-thiazolidinone
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About This Item
Empirical Formula (Hill Notation):
C3H3NOS2
CAS Number:
Molecular Weight:
133.19
Beilstein:
110701
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
97%
form
solid
mp
165-169 °C (lit.)
solubility
methanol: soluble 2.5%, clear (yellow-green to orange-brown)
SMILES string
O=C1CSC(=S)N1
InChI
1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
InChI key
KIWUVOGUEXMXSV-UHFFFAOYSA-N
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General description
Rhodanine possess anticonvulsant, antibacterial, antiviral and antidiabetic activities.
Application
Rhodanine has been used in tannase assay in cultures of tannin degrading fungi.
Biochem/physiol Actions
Rhodanine inhibits the multiplication of echovirus 12 and the development of virus-induced morphologic changes.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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H J Eggers et al.
Science (New York, N.Y.), 167(3916), 294-297 (1970-01-16)
A search for compounds which have previously unrecognized antiviral activity led to the discovery that rhodanine inhibits the multiplication of echovirus 12 and also the development of virus-induced morphologic changes. Eighteen derivatives and analogs of rhodanine were synthesized and tested
Culture conditions for the production of a tannase of Aspergillus tamarii IMI388810 (B).
Enemuor SC and Odibo FJC.
African Journal of Biotechnology, 8(11), 2554-2557 (2009)
Neil S Cutshall et al.
Bioorganic & medicinal chemistry letters, 15(14), 3374-3379 (2005-06-18)
Dual-specificity phosphatases (DSPs) are a subclass within the protein tyrosine phosphatase family (PTPs). A series of rhodanine-based inhibitors was synthesized and shown to be novel, potent, and selective inhibitors against the DSP family member JNK-stimulating phosphatase-1 (JSP-1). Compounds of this
Tihomir Tomašić et al.
Expert opinion on drug discovery, 7(7), 549-560 (2012-05-23)
Rhodanine-based compounds have been associated with numerous biological activities. After many years of research in drug discovery, they have gained a reputation as being pan assay interference compounds (PAINS) and frequent hitters in screening campaigns. Rhodanine-based compounds are also aggregators
T Tomasić et al.
Current medicinal chemistry, 16(13), 1596-1629 (2009-05-16)
Rhodanines, thiazolidine-2,4-diones and pseudothiohydantoins have become a very interesting class of heterocyclic compounds since the introduction of various glitazones and epalrestat into clinical use for the treatment of type II diabetes mellitus and diabetic complications, respectively. Chemical modifications of these
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