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

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

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ChEBI ID	CHEBI:167669
ChEBI Name	(E)-2-[[[4-(2-chlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]benzoic acid
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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.
Last Modified	12 April 2021
Submitter	R. Stephan
Downloads	Molfile

Formula	C17H12ClN3O2S
Net Charge	0
Average Mass	357.822
Monoisotopic Mass	357.03388
SMILES	O=C(O)c1ccccc1/C=N/Nc1nc(-c2ccccc2Cl)cs1
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

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. antiviral agent A substance that destroys or inhibits replication of viruses. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. 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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	(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

Manual Xrefs	Databases
3X2	PDBeChem

Citations