Phenol, 3-[(6,7-diMethoxy-4-quinazolinyl)aMino]-

Product NamePhenol, 3-[(6,7-diMethoxy-4-quinazolinyl)aMino]-
CAS211555-08-7
MFC16H15N3O3
MW297.31
EINECS
MOL File211555-08-7.mol

Chemical Properties

Boiling point	476.5±40.0 °C(Predicted)
Density	1.336±0.06 g/cm3(Predicted)
storage temp.	2-8°C(protect from light)
solubility	DMSO : 25 mg/mL (84.09 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
form	Powder
pka	9.58±0.10(Predicted)
color	White to off-white
InChI	1S/C16H15N3O3/c1-21-14-7-12-13(8-15(14)22-2)17-9-18-16(12)19-10-4-3-5-11(20)6-10/h3-9,20H,1-2H3,(H,17,18,19)
InChIKey	BNDYIYYKEIXHNK-UHFFFAOYSA-N
SMILES	N(c3cc(ccc3)O)c1ncnc2c1cc(c(c2)OC)OC

Safety Information

WGK Germany	WGK 1
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

WHI-P180 (Janex 3) is a multi-kinase inhibitor; inhibits RET, KDR and EGFR with IC50s of 5 nM, 66 nM and 4 μM, respectively.

Biological Activity

WHI-P180 is an inhibitor of multiple kinases with IC50 values of 4.5 nM and 66 nM for RET (c-RET) and KDR, respectively.

in vivo

WHI-P180 is also an active inhibitor of IgE-mediated mast cell responses. The elimination half-life of WHI-P180 in CD-1 mice (BALB/c mice) following iv, ip, or po administration is less than 10 min. Systemic clearance of WHI-P180 is 6742 mL/h/kg in CD-I mice and 8188 mL/h/kg in BALB/c mice. Notably, WHI-P180, when administered in two consecutive nontoxic ip bolus doses of 25 mg/kg, inhibits IgE/antigen-induced vascular hyperpermeability in a well-characterized murine model of passive cutaneous anaphylaxis.

target

Target	Value
RET (Cell-free assay)	4.5 nM
KDR (Cell-free assay)	66 nM

IC 50

EGFR: 4 μM (IC₅₀); KDR: 66 nM (IC₅₀); RET: 5 nM (IC₅₀)

References

[1] Newton R, et al. The discovery of 2-substituted phenol quinazolines as potent RET kinase inhibitors with improved KDR selectivity. Eur J Med Chem. 2016 Apr 13;112:20-32. DOI:10.1016/j.ejmech.2016.01.039
[2] Ghosh S, et al. 4-[3-Bromo-4-hydroxyphenyl)amino]-6,7-dimethoxyquinazolin-1-ium chloride methanol solvateand 4-[(3-hydroxyphenyl)amino]-6,7-dimethoxy-1-quinazolinium chloride. Acta Crystallogr C. 2001 Jan;57(Pt 1):76-8. DOI:10.1107/s0108270100013561
[3] Chen CL, et al. Pharmacokinetics and biologic activity of the novel mast cell inhibitor, 4-(3-hydroxyphenyl)-amino-6,7-dimethoxyquinazoline in mice. Pharm Res. 1999 Jan;16(1):117-22. DOI:10.1023/a:1018835232027

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