(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302)

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ChEBI Name	(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione

ChEBI ID	CHEBI:45302

ChEBI ASCII Name	(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione

Definition	A quinoxaline derivative that is quinoxaline in which the hydrogen at position 6 is replaced by a (2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl group. It is a potent inhibitor of the PI3Kγ, with an IC₅₀ of 8 nM and inhibits the progression of joint inflammation and damage in both lymphocyte-independent and dependent mouse models of rheumatoid arthritis.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C12H7N3O2S

Net Charge

Average Mass

257.270

Monoisotopic Mass

257.02590

InChI

InChI=1S/C12H7N3O2S/c16-11-10(18-12(17)15-11)6-7-1-2-8-9(5-7)14-4-3-13-8/h1-6H,(H,15,16,17)/b10-6-

InChIKey

SQWZFLMPDUSYGV-POHAHGRESA-N

SMILES

O=C1NC(=O)\C(S1)=C\C1=CC2=C(C=C1)N=CC=N2

Roles Classification
Biological Role(s):	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor An inhibitor of phosphatidylinositol 3-kinase, EC 2.7.1.137, a family of related enzymes capable of phosphorylating the 3 position hydroxy group of the inositol ring of a phosphatidylinositol.

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects. antirheumatic drug A drug used to treat rheumatoid arthritis.

ChEBI Ontology
Outgoing	(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302) has role anti-inflammatory agent (CHEBI:67079) (5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302) has role antirheumatic drug (CHEBI:35842) (5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302) has role EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor (CHEBI:50914) (5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302) is a quinoxaline derivative (CHEBI:38771) (5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione (CHEBI:45302) is a thiazolidinediones (CHEBI:50990)

IUPAC Name

(5Z)-5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione

Synonyms	Sources
5-(6-quinoxalinylmethylene)-2,4-thiazolidinedione	ChEBI
5-[(quinoxalin-6-yl)methylidene]-1,3-thiazolidine-2,4-dione	ChEBI
5-quinoxalin-6-ylmethylene-thiazolidine-2,4-dione	ChEBI
5-quinoxalin-6-ylmethylenethiazolidine-2,4-dione	ChEBI
AS 605240	LINCS
AS-605240	ChemIDplus
AS605240	ChEBI

Registry Number	Type	Source
648450-29-7	CAS Registry Number	ChemIDplus

Last Modified

25 September 2020