4-N-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine

• ChemBase ID: 160392
• Molecular Formular: C22H20N4O
• Molecular Mass: 356.4204
• Monoisotopic Mass: 356.16371128
• SMILES: c1c(ccc2c1c(ncn2)NCCc1ccc(cc1)Oc1ccccc1)N
• Canonical SMILES: Nc1ccc2c(c1)c(NCCc1ccc(cc1)Oc1ccccc1)ncn2
• InChI: InChI=1S/C22H20N4O/c23-17-8-11-21-20(14-17)22(26-15-25-21)24-13-12-16-6-9-19(10-7-16)27-18-4-2-1-3-5-18/h1-11,14-15H,12-13,23H2,(H,24,25,26)
• InChIKey: IBAKVEUZKHOWNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-N-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine; N4-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine
• IUPAC Traditional name: 4-N-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine; N4-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine
• Synonyms: N4-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediamine; QNZ; 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline; QNZ (EVP4593)

Database IDs

• CAS Number: 545380-34-5
• PubChem SID: 162254527
• PubChem CID: 509554

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.940716
• LogD (pH = 7.4): 4.172824
• Log P: 4.1767936
• Molar Refractivity: 109.6166 cm^3
• Polarizability: 41.902122 Å^3
• Polar Surface Area: 73.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 169-175°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

Pharmacology Properties

• Target: NF-κB

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - A621350

QNZ is a novel inhibitor of NFkB which displays potent inhibitory effects on both NFKB transcriptional activation (IC50=11nM) and TNF-α production (IC50=7nM). It dose-dependently inhibited carragenin-induced edema formation in the rat paw model (1mg/Kg).

REFERENCES

• Tobe, M., et al.: Bioorg. Med. Chem., 11, 3869 (2003)
• Choi, S., et al.: J. Biol. Chem., 281, 12722 (2006)