N-[9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl]-2-phenylacetamide

• ChemBase ID: 132285
• Molecular Formular: C21H14ClN5O2
• Molecular Mass: 403.82116
• Monoisotopic Mass: 403.08360239
• SMILES: c1ccc(cc1)CC(=O)Nc1nc2ccc(cc2c2n1nc(n2)c1ccco1)Cl
• Canonical SMILES: O=C(Nc1nc2ccc(cc2c2n1nc(n2)c1ccco1)Cl)Cc1ccccc1
• InChI: InChI=1S/C21H14ClN5O2/c22-14-8-9-16-15(12-14)20-25-19(17-7-4-10-29-17)26-27(20)21(23-16)24-18(28)11-13-5-2-1-3-6-13/h1-10,12H,11H2,(H,23,24,28)
• InChIKey: TWWFAXQOKNBUCR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl]-2-phenylacetamide
• IUPAC Traditional name: N-[9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl]-2-phenylacetamide
• Synonyms: 9-Chloro-2-(2-furanyl)-5-((phenylacetyl)amino)-[1,2,4]triazolo[1,5-c]quinazoline; MRS 1220

Database IDs

• CAS Number: 183721-15-5
• MDL Number: MFCD01321046
• PubChem SID: 162226562; 24896720
• PubChem CID: 393595

CALCULATED PROPERTIES

• Acid pKa: 9.167413
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.2890244
• LogD (pH = 7.4): 5.2820215
• Log P: 5.289121
• Molar Refractivity: 130.6909 cm^3
• Polarizability: 42.52708 Å^3
• Polar Surface Area: 85.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 2-hydroxypropyl-β-cyclodextrin: insoluble; DMSO: soluble2 mg/mL; ethanol: insoluble; H2O: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

DETAILS

Sigma Aldrich - M228

Biochem/physiol Actions
MRS1220 is a putative A3 adenosine receptor antagonist. MRS 1220 was found to be competitive in saturation binding studies using the agonist radioligand 125I AB-MECA at cloned human brain A3 receptors expressed in HEK-293 cells. Antagonism was demonstrated in functional assays consisting of agonist-induced inhibition of adenylate cyclase and the stimulation of binding of 35S guanosine 5′-O-(3-thiotriphosphate (35S GTP-gamma-S) to the associated G-proteins. MRS 1220 and MRS 1191, with KB values of 1.7 and 92 nM, respectively, proved to be highly selective for human A3 receptor vs human A1 receptor-mediated effects on adenylate cyclase. In addition, MRS 1220 reversed the effect of A3 agonist-elicited inhibition of tumor necrosis factor-alpha formation in the human macrophage U-937 cell line, with an IC50 value of 0.3 μM.