4-[2-(4-{3-phenylpyrazolo[1,5-a]pyrimidin-6-yl}phenoxy)ethyl]morpholine

• ChemBase ID: 154798
• Molecular Formular: C24H24N4O2
• Molecular Mass: 400.47296
• Monoisotopic Mass: 400.18992603
• SMILES: c1ccc(cc1)c1cnn2c1ncc(c2)c1ccc(cc1)OCCN1CCOCC1
• Canonical SMILES: O1CCN(CC1)CCOc1ccc(cc1)c1cnc2n(c1)ncc2c1ccccc1
• InChI: InChI=1S/C24H24N4O2/c1-2-4-20(5-3-1)23-17-26-28-18-21(16-25-24(23)28)19-6-8-22(9-7-19)30-15-12-27-10-13-29-14-11-27/h1-9,16-18H,10-15H2
• InChIKey: SKZQZGSPYYHTQG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(4-{3-phenylpyrazolo[1,5-a]pyrimidin-6-yl}phenoxy)ethyl]morpholine
• IUPAC Traditional name: 4-[2-(4-{3-phenylpyrazolo[1,5-a]pyrimidin-6-yl}phenoxy)ethyl]morpholine
• Synonyms: DMH4

Database IDs

• CAS Number: 515880-75-8
• MDL Number: MFCD18452839
• PubChem SID: 162248936
• PubChem CID: 5329447

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.443565
• LogD (pH = 7.4): 3.5237925
• Log P: 3.5898962
• Molar Refractivity: 127.6028 cm^3
• Polarizability: 47.572918 Å^3
• Polar Surface Area: 51.89 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL
• Apperance: off-white to brown powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: >99.0% (HPLC)
• Empirical Formula (Hill Notation): C24H24 N4O2

DETAILS

Sigma Aldrich - D8696

Biochem/physiol Actions
DMH4 is a potent VEGF inhibitor and an angiogenesis inhbitor. It is a selective VEGF inhibitor with an IC50 of 161 nM for VEGFR inhibition compared to 8000 nM for AMPK. Unlike the structurally similar DMH1, which is a selective BMP inhibitor, DMH4 shows little affinitiy for BMP with an IC50 of 3500 nM for BMPR-I.