A quinolinecarboxylic acid derivative with immunosuppressive and anti-neoplastic properties. Inhibits pyrimidine synthesis by blocking the activity of mammalian mitochondrial dihydroorotate dehydrogenase (DHODH; IC50 = 12 nM). Does not affect DHODH in non-mammalian species. Also reported to inhibit glycosylation of adhesion molecules. Potentiates the sensitivity of U1690 small cell lung cancer cells to TRAIL-induced apoptosis and synergistically enhances the anti-tumor effects of doxorubicin ( ~100 µM).

Spécifications

Synonymes

BRQ, DuP 785, NSC 368390 | 6-Fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium

Spécifications et pureté

≥95%

Mécanismes biochimiques et physiologiques

Potent and selective dihydroorotate dehydrogenase (DHODH) inhibitor (IC50= ~20 nM). Causes depletion of pyrimidine nucleotides. Exhibits minimal inhibition against a panel of >400 kinases. Triggers differentiation of AML cell lines (ED50= ~ 1 μM. Note uri

Conditions de stockage de stockage

Store at -20°C,Argon charged

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥95%

Noms et identifiants

Pubchem Sid

528771629

Sourires canoniques

CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)[O-].[Na+]

IUPAC Name

sodium;6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylate

InChIKey

PZOHOALJQOFNTB-UHFFFAOYSA-M

INCHI

1S/C23H15F2NO2.Na/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25;/h2-12H,1H3,(H,27,28);/q;+1/p-1

Isomères SMILES

CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)[O-].[Na+]

Poids moléculaire

397.35

Reaxy-Rn

6466194

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6466194&ln=

Données avancées

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organoheterocyclic compounds
  - Classe Quinolines and derivatives
    - Subclass Phenylquinolines

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Classe	Quinolines and derivatives
Subclass	Phenylquinolines
Intermediate Tree Nodes	Not available
Direct Parent	Phenylquinolines
Alternative Parents	Quinoline carboxylic acids Phenylpyridines Biphenyls and derivatives Haloquinolines Pyridinecarboxylic acids Fluorobenzenes Methylpyridines Aryl fluorides Heteroaromatic compounds Carboxylic acid salts Azacyclic compounds Carboxylic acids Organic metal halides Organic sodium salts Organic zwitterions Organooxygen compounds Organofluorides Organic oxides Hydrocarbon derivatives Organonitrogen compounds
Molecular Framework	Aromatic heteropolycyclic compounds
Substituents	Phenylquinoline - Quinoline-4-carboxylic acid - Biphenyl - 2-phenylpyridine - Haloquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Fluorobenzene - Halobenzene - Methylpyridine - Monocyclic benzene moiety - Benzenoid - Aryl fluoride - Aryl halide - Pyridine - Heteroaromatic compound - Carboxylic acid salt - Azacycle - Organic metal halide - Organic alkali metal salt - Carboxylic acid derivative - Carboxylic acid - Hydrocarbon derivative - Organofluoride - Organohalogen compound - Organic zwitterion - Organonitrogen compound - Organic sodium salt - Organooxygen compound - Organic nitrogen compound - Organic salt - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Structure 3D

Cibles associées (humaines)

DHODH Tclin Dihydroorotate dehydrogenase (quinone), mitochondrial (6 Activities)

Discover Target: DHODH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

Discover Target: DHODH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A-375 (9258 Activities)

Solubilité	Solvent:water, Max Conc. mg/mL: 39.73, Max Conc. mM: 100; Solvent:DMSO, Max Conc. mg/mL: 39.73, Max Conc. mM: 100
Poids moléculaire	397.300 g/mol
XLogP3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	397.089 Da
Monoisotopic Mass	397.089 Da
Topological Polar Surface Area	53.000 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	557.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	2

Brequinar sodium - ≥95% , CAS No.96201-88-6

Vue d’ensemble

Spécifications

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