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Sigma-Aldrich

Rhodanine

97%

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Synonym(s):
2-Thioxo-4-thiazolidinone
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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Feng Yu et al.
Organic letters, 14(8), 2038-2041 (2012-04-10)
A bulky group was introduced by design into a diamine catalyst, and a series of robust and tunable bulky chiral primary amine catalysts were developed and successfully applied in the direct conjugate addition of substituted rhodanines to α,β-unsaturated ketones. High
Thomas Mendgen et al.
Journal of medicinal chemistry, 55(2), 743-753 (2011-11-15)
Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based

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