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118192

Sigma-Aldrich

Rhodanine

97%

Synonym(s):

2-Thioxo-4-thiazolidinone

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About This Item

Empirical Formula (Hill Notation):
C3H3NOS2
CAS Number:
141-84-4
Molecular Weight:
133.19
Beilstein:
110701
EC Number:
205-505-1
MDL number:
MFCD00005488
UNSPSC Code:
12352100
PubChem Substance ID:
24847363
NACRES:
NA.22

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
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

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

Certificates of Analysis (COA)

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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
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)
Parminder Singh et al.
Biochemistry, 51(27), 5434-5442 (2012-06-19)
A perturbation of FtsZ assembly dynamics has been shown to inhibit bacterial cytokinesis. In this study, the antibacterial activity of 151 rhodanine compounds was assayed using Bacillus subtilis cells. Of 151 compounds, eight strongly inhibited bacterial proliferation at 2 μM.
Ming-Xia Song et al.
European journal of medicinal chemistry, 54, 403-412 (2012-06-19)
Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 μg/mL.
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