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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)
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.
Matjaž Brvar et al.
Bioorganic & medicinal chemistry, 20(8), 2572-2580 (2012-03-27)
Bacterial DNA gyrase is an established and validated target for the development of novel antibacterials. In our previous work, we identified a novel series of bacterial gyrase inhibitors from the class of 4-(2,4-dihydroxyphenyl) thiazoles. Our ongoing effort was designated to
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