N-[(4-{[(pyridin-2-yl)amino]methyl}phenyl)methyl]pyridin-2-amine

• ChemBase ID: 155042
• Molecular Formular: C18H18N4
• Molecular Mass: 290.36232
• Monoisotopic Mass: 290.1531466
• SMILES: c1ccnc(c1)NCc1ccc(cc1)CNc1ccccn1
• Canonical SMILES: c1ccc(nc1)NCc1ccc(cc1)CNc1ccccn1
• InChI: InChI=1S/C18H18N4/c1-3-11-19-17(5-1)21-13-15-7-9-16(10-8-15)14-22-18-6-2-4-12-20-18/h1-12H,13-14H2,(H,19,21)(H,20,22)
• InChIKey: KBVFRXIGQQRMEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-{[(pyridin-2-yl)amino]methyl}phenyl)methyl]pyridin-2-amine
• IUPAC Traditional name: N-({4-[(pyridin-2-ylamino)methyl]phenyl}methyl)pyridin-2-amine
• Synonyms: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine; WZ811; WZ 811

Database IDs

• CAS Number: 55778-02-4
• MDL Number: MFCD18086914
• PubChem SID: 162249180
• PubChem CID: 11565518

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.1599545
• LogD (pH = 7.4): 2.9997108
• Log P: 3.1213186
• Molar Refractivity: 91.984 cm^3
• Polarizability: 33.701206 Å^3
• Polar Surface Area: 49.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥7 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: CXCR

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H18N4

DETAILS

Sigma Aldrich - SML0088

Biochem/physiol Actions
WZ811 is a potent, specific antagonist of CXCR4 (IC50 = 0.3 nM). WZ811 blocks SDF-1 mediated changes in cellular cAMP levels in U87 glioma cells (IC50 = 1.2 nM) and Matirgel infiltration of MDA-MB-231 cells (IC50 = 5.2 nM).