3-(6-{[4-(trifluoromethoxy)phenyl]amino}pyrimidin-4-yl)benzamide

• ChemBase ID: 153875
• Molecular Formular: C18H13F3N4O2
• Molecular Mass: 374.3166296
• Monoisotopic Mass: 374.09906034
• SMILES: c1cc(cc(c1)C(=O)N)c1cc(ncn1)Nc1ccc(cc1)OC(F)(F)F
• Canonical SMILES: NC(=O)c1cccc(c1)c1ncnc(c1)Nc1ccc(cc1)OC(F)(F)F
• InChI: InChI=1S/C18H13F3N4O2/c19-18(20,21)27-14-6-4-13(5-7-14)25-16-9-15(23-10-24-16)11-2-1-3-12(8-11)17(22)26/h1-10H,(H2,22,26)(H,23,24,25)
• InChIKey: WEVYNIUIFUYDGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(6-{[4-(trifluoromethoxy)phenyl]amino}pyrimidin-4-yl)benzamide
• IUPAC Traditional name: 3-(6-{[4-(trifluoromethoxy)phenyl]amino}pyrimidin-4-yl)benzamide
• Synonyms: 3-[6-[[4-(Trifluoromethoxy)phenyl]amino]-4-pyrimidinyl]benzamide; GNF-2; GNF-2

Database IDs

• CAS Number: 778270-11-4
• MDL Number: MFCD09265253
• PubChem SID: 162248014; 24724498
• PubChem CID: 5311510

CALCULATED PROPERTIES

• Acid pKa: 14.464547
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.386804
• LogD (pH = 7.4): 4.3987913
• Log P: 4.3989463
• Molar Refractivity: 88.4349 cm^3
• Polarizability: 34.78228 Å^3
• Polar Surface Area: 90.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL; H2O: <2 mg/mL
• Apperance: off-white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Bcr-Abl

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H13F3N4O2

DETAILS

Sigma Aldrich - G9420

Biochem/physiol Actions
GNF-2 belongs to a new class of Bcr-abl inhibitors. GNF-2 appears to bind to the myristoyl binding pocket, an allosteric site distant from the active site, stabilizing the inactive form of the kinase. It inhibits Bcr-abl phosphorylation with an IC50 of 267 nM, but does not inhibit a panel of 63 other kinases, including native c-Abl, and shows complete lack of toxicity towards cells not expressing Bcr-Abl. GNF-2 shows great potential for a new class of inhibitor to study Bcr-abl activity and to treat resistant Chronic myelogenous leukemia (CML), which is caused the Bcr-Abl oncoprotein.