(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669)

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ChEBI Name	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid

ChEBI ID	CHEBI:167669

ChEBI ASCII Name	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid

Definition	A member of the class of 1,3-thiazoles that is 1,3-thiazole substituted by (2E)-2-(2-carboxybenzylidene)hydrazinyl and 2-chlorophenyl groups at positions 2 and 4, respectively. It is a potent inhibitor of human dihydroorotate dehydrogenase (hDHODH) with IC₅₀ of 32 nM. It exhibits antineoplastic activity and broad-spectrum antiviral activity against various RNA viruses including influenza A, Zika, Ebola, and SARS-CoV-2 viruses.

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

Submitter	R. Stephan

Supplier Information

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Formula

C17H12ClN3O2S

Net Charge

Average Mass

357.810

Monoisotopic Mass

357.03388

InChI

InChI=1S/C17H12ClN3O2S/c18-14-8-4-3-7-13(14)15-10-24-17(20-15)21-19-9-11-5-1-2-6-12(11)16(22)23/h1-10H,(H,20,21)(H,22,23)/b19-9+

InChIKey

DDEIFUOYHWEWSS-DJKKODMXSA-N

SMILES

OC(=O)C1=C(\C=N\NC2=NC(=CS2)C2=CC=CC=C2Cl)C=CC=C1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor An EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of dihydroorotate dehydrogenase (quinone), EC 1.3.5.2. antiviral agent A substance that destroys or inhibits replication of viruses. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role anticoronaviral agent (CHEBI:149553) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role antineoplastic agent (CHEBI:35610) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role antiviral agent (CHEBI:22587) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role apoptosis inducer (CHEBI:68495) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) has role EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor (CHEBI:77103) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a 1,3-thiazoles (CHEBI:38418) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a benzoic acids (CHEBI:22723) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a hydrazone (CHEBI:38532) (E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid (CHEBI:167669) is a monochlorobenzenes (CHEBI:83403)

IUPAC Name

2-[(E)-{2-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene}methyl]benzoic acid

Synonym	Source
S312	SUBMITTER

Citation	Type	Source
32754890	PubMed citation	SUBMITTER

Last Modified

12 April 2021

General Comment
2021-04-12	Additional Info: https://doi.org/10.1039/C6MD00179C