6-(phenylamino)-5,8-dihydroquinoline-5,8-dione

• ChemBase ID: 91023
• Molecular Formular: C15H10N2O2
• Molecular Mass: 250.2521
• Monoisotopic Mass: 250.07422757
• SMILES: n1cccc2c1C(=O)C=C(C2=O)Nc1ccccc1
• Canonical SMILES: O=C1C=C(Nc2ccccc2)C(=O)c2c1nccc2
• InChI: InChI=1S/C15H10N2O2/c18-13-9-12(17-10-5-2-1-3-6-10)15(19)11-7-4-8-16-14(11)13/h1-9,17H
• InChIKey: GXIJYWUWLNHKNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(phenylamino)-5,8-dihydroquinoline-5,8-dione
• IUPAC Traditional name: 6-(phenylamino)quinoline-5,8-dione
• Synonyms: 6-(Phenylamino)-5,8-quinolinedione; LY-83,583; LY83583; 6-Anilinoquinoline-5,8-quinone; 5,8-Dihydro-5,8-dioxo-6-(phenylamino)quinoline, [(5,8-Dihydro-5,8-dioxoquinolin-6-yl)amino]benzene; 6-Anilinoquinoline-5,8-dione; 6-(Phenylamino)quinoline-5,8-dione; 6-Anilinoquinoline-5,8-quinone; 5,8-Dihydro-5,8-dioxo-6-(phenylamino)quinoline; LY 83583; 6-ANILINO-5,8-QUINOLINEDIONE

Database IDs

• CAS Number: 91300-60-6
• MDL Number: MFCD00210756
• PubChem SID: 24891108; 162077727
• PubChem CID: 3976

CALCULATED PROPERTIES

• Acid pKa: 11.12437
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.5780785
• LogD (pH = 7.4): 1.5780628
• Log P: 1.57814
• Molar Refractivity: 73.6122 cm^3
• Polarizability: 26.668064 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble1 mg/mL; Dichloromethane; ethanol: soluble8 mg/mL; methanol: soluble11 mg/mL
• Apperance: Red-Brown Solid; violet solid
• Melting Point: 184-185°C; 184-185°C

Safety Information

• Storage Warning: Irritant/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (TLC); 97%

DETAILS

MP Biomedicals - 02158866

(LY 83583)
Purity: 97%
Inhibits nitric oxide induced activation of soluble guanylate cyclase. Also enhances contractile responses of rat aorta and artery to α-adrenoceptor agonists. Blocks leukotriene releases and acetylcholine induced rela

Apollo Scientific Ltd - OR6450T

Inhibits nitric-oxide-induced activation of soluble guanylate cyclase(IC50=2uM)in a dose-dependent &reversible manner. It blocks acetylcholine inducedvasorelaxation.

Sigma Aldrich - A6563

Biochem/physiol Actions
Blocks cGMP production; inhibits intracellular Ca2+ release; blocks the effects of nitric oxide. Inhibits antigen-induced leukotriene release.
Application
6-Anilinoquinoline-5,8-quinone inhibits soluble guanylate cyclase and cGMP production. 6-Anilinoquinoline-5,8-quinone also blocks the release of intracellular Ca2+ and antigen-induced leukotrienes.

Toronto Research Chemicals - A664500

Inhibits nitric-oxide-induced activation of soluble guanylate cyclase (IC50=2μM) in a dose-dependent and reversible manner. It blocks acetylcholine induced vasorelaxation. Also an inhibitor of antigen-induced leukotriene release.

REFERENCES

• Macleod, K.M., et al.: Mol. Pharmacol., 32, 59 (1987)
• Mulsch, A. J.: J. Pharmacol. Exp. Ther., 247, 283 (1987)
• Mulsch, A., et al.: Naunyn-Schmiedeberg's Arch. Pharmacol., 340, 119 (1987)
• Light, D.B., et al.: Science, 243, 383 (1987)
• Beasley, D., et al