rhodanine

Also known as 2-sulfanylidene-4-thiazolidinone, 2-sulfanylidene-1,3-thiazolidin-4-one, 2-thioxothiazolidin-4-one, 2-thioxo-4-thiazolidinone

Rhodanine is a 5-membered heterocyclic organic compound possessing a thiazolidine core. It was discovered in 1877 by Marceli Nencki who named it "Rhodaninsaure" in reference to its synthesis from ammonium rhodanide (known as ammonium thiocyanate to modern chemists) and chloroacetic acid in water.

Chemical data

Formula: C3H3NOS2
Molecular weight: 133.2 g/mol
IUPAC name: 2-sulfanylidene-1,3-thiazolidin-4-one

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

1,057 papers

Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents.Chemical biology & drug design · 2023
Drug screening of rhodanine derivatives for antibacterial activity.Expert opinion on drug discovery · 2020
Review of anticancer potentials and structure-activity relationships (SAR) of rhodanine derivatives.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
Arylidene and amino spacer-linked rhodanine-quinoline hybrids as upgraded antimicrobial agents.Chemical biology & drug design · 2023
The Importance of Rhodanine Scaffold in Medicinal Chemistry: A Comprehensive Overview.Mini reviews in medicinal chemistry · 2021

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 132.965606

Show 5 more facts

chemical formula: C₃H₃NOS₂
canonical SMILES: C1C(=O)NC(=S)S1
melting point: 169
different from: rhodamine
Commons category: Rhodanine

Sources (5)

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Encyclopedic overview

2 sections

Contents

Derivatives
References

Rhodanines can also be prepared by the reaction of carbon disulfide, ammonia, and chloroacetic acid, which proceeds via an intermediate dithiocarbamate. 450px|frameless

Excerpted from Wikipedia’s “rhodanine” article, available under the CC BY-SA 4.0 licence.