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167869-21-8 molecular structure
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2-(2-amino-3-methoxyphenyl)-4H-chromen-4-one

ChemBase ID: 72560
Molecular Formular: C16H13NO3
Molecular Mass: 267.27932
Monoisotopic Mass: 267.08954328
SMILES and InChIs

SMILES:
c1ccc2c(c1)c(=O)cc(o2)c1cccc(c1N)OC
Canonical SMILES:
COc1cccc(c1N)c1cc(=O)c2c(o1)cccc2
InChI:
InChI=1S/C16H13NO3/c1-19-14-8-4-6-11(16(14)17)15-9-12(18)10-5-2-3-7-13(10)20-15/h2-9H,17H2,1H3
InChIKey:
QFWCYNPOPKQOKV-UHFFFAOYSA-N

Cite this record

CBID:72560 http://www.chembase.cn/molecule-72560.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(2-amino-3-methoxyphenyl)-4H-chromen-4-one
IUPAC Traditional name
2-(2-amino-3-methoxyphenyl)chromen-4-one
Synonyms
PD98059
2-(2-Amino-3-methoxyphenyl)-4H-1-benzopyran-4-one
PD98059
PD 98,059
PD 98059
2'-AMINO-3'-METHOXYFLAVONE
CAS Number
167869-21-8
MDL Number
MFCD00671789
PubChem SID
162037485
24278666
PubChem CID
4713

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 4713 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.626329  H Acceptors
H Donor LogD (pH = 5.5) 1.9785058 
LogD (pH = 7.4) 1.980759  Log P 1.9807879 
Molar Refractivity 78.1348 cm3 Polarizability 28.923859 Å3
Polar Surface Area 61.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: soluble10 mg/mL, clear expand Show data source
Apperance
yellow solid expand Show data source
Storage Condition
-20°C expand Show data source
-20°C, Desiccate, Protect from light expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
-20°C expand Show data source
Target
MEK expand Show data source
Gene Information
human ... MAP2K1(5604), MAP2K2(5605), MAP2K3(5606), MAP2K4(6416), MAP2K5(5607), MAP2K6(5608), MAP2K7(5609), MAP3K1(4214), RAF1(5894) expand Show data source
Purity
>95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02195935 external link
Purity: >95%
MAP kinase activation inhibitor. Inhibits cell growth and reverses the phenotype of ras -transformed BalB 3T3 fibroblasts.
Selleck Chemicals - S1177 external link
Research Area
Description Cancer
Biological Activity
Description PD98059 is a non-competitive MEK inhibitor with IC50 of 2 μM.
Targets MEK1
IC50 2 μM [1]
In Vitro PD98059 inhibits either basal MEK1 or a partially activated MEK produced by mutation of serine at residues 218 and 222 to glutamate (MEK-2E) with IC50 of 2 μM. PD98059 does not inhibit the MAPK homologues JNK and P38. PD98059 is highly selective against MEK, as it does not inhibit a number of other kinase activities including Raf kinase, cAMP-dependent kinase, protein kinase C, v-Src, epidermal growth factor (EGF) receptor kinase, insulin receptor kinase, PDGF receptor kinase, and phosphatidylinositol 3-kinase. PD98059 inhibits PDGF-stimulated activation of MAPK and thymidine incorporation into 3T3 cells with IC50 of ~10 μM and ~7 μM, respectively. [1] PD98059 potently prevents the activation of MEK1 by Raf or MEK kinase with IC50 of 4 μM, and weakly inhibits the activation of MEK2 by Raf with IC50 of 50 μM. PD98059 does not inhibit the activation of MEK homologues MKK4 and RK kinase that participate in stress and interleukin-1-stimulated kinase cascades in KB and PC12 cells, and the activation of p70 S6 kinase by insulin or epidermal growth factor in Swiss 3T3 cells. [2] PD98059 completely blocks the nerve growth factor (NGF)-induced differentiation of PC12 cells without altering cell viability. [3] PD98059 inhibits the proliferation of RAW264.7 cells in the culture containing RANKL in a dose-dependent manner, resulting in an apparent decrease of TRAP-positive cells. [6]
In Vivo Treatment of mice 30 minutes before focal cerebral ischemia with PD98059 protects against damage, resulting in a decrease in infarct volume. [4] Pretreated with PD98059 (10 mg/kg per i.v. injection) 30 minutes before and then together with hourly cerulein injections for 3 hours significantly ameliorates cerulein-induced acute pancreatitis ipancreatitis on the basis of pancreatic wet weight and histology. [7] Administration of PD98059 (10 mg/kg) in mice 1 hour after carrageenan causes a reduction in all the parameters of inflammation measured. [11]
Clinical Trials
Features Not inhibits c-Raf phosphorylated MEK1
Combination Therapy
Description PD98059 pre-treatment sensitizes the human melanoma cell line C8161 to Cisplatin-induced apoptosis. Concomitant addition of PD98059 and Cisplatin does not have any sensitizing effect. [5] In androgen-independent C-81 LNCaP cells, PD98059, but not U0126, plus Docetaxel results in enhanced growth suppression by an additional 20% compared to the sum of each agent alone, and enhances docetaxel-induced apoptosis. [8] PD98059 in combination with LY294002 synergistically induces apoptosis of human leukemic U937 cells. [9] PD98059 acts synergistically with Nutlin-3A to induce apoptosis in wild-type p53 AML cell lines OCI-AML-3 and MOLM-13. [10]
Protocol
Kinase Assay [1]
In vitro MEK-inhibitory activity Incorporation of 32P into myelin basic protein (MBP) is assayed in the presence of glutathione S-transferase (GST) fusion proteins containing the 44-kDa MAPK (GST-MAPK) or the 45-kDa MEK (GST-MEK1). Assays are conducted in 50 μL of 50 mM Tris, pH 7.4/10 mM MgCl2/2 mM EGTA/10 μM [γ-32P]ATP containing 10 μg of GST-MEK1, 0.5 μg of GST-MAPK, and 40 μg of MBP. After incubation at 30°C for 15 minutes, reactions are stopped by addition of Laemmli SDS sample buffer. Phosphorylated MBP is resolved by SDS/10% PAGE.
Cell Assay [1]
Cell Lines K-Balb, KNRK, v-raf-3Y1, SRA/3Y1, EGFR/3T3, and K562
Concentrations Dissolved in DMSO, final concentrations ~100 μM
Incubation Time 3 dyas, or 7-10 days
Methods For monolayer growth, cells are plated into multi-well plates at 10,000-20,000/mL. Forty-eight hours later, various concentrations of PD98059 are added to the cell growth medium and incubation is continued for an additional 3 days. Cells are then removed from the wells by incubation with trypsin and enumerated with a Coulter Counter. For growth in soft agar, cells are seeded into 35-mm dishes at 5,000-10,000 cells per dish with growth medium containing 0.3% agar and desired concentrations of PD98059. After 7-10 days of growth, visible colonies are manually enumerated with the aid of a dissecting microscope.
Animal Study [7]
Animal Models Male Sprague–Dawley rats with acute pancreatitis
Formulation Dissolved in DMSO, and diluted in saline
Doses 10 mg/kg
Administration Injection i.v.
References
[1] Dudley DT, et al. Proc Natl Acad Sci U S A, 1995, 92(17), 7686-7689.
[2] Alessi DR, et al. J Biol Chem, 1995, 270(46), 27489-27494.
[3] Pang L, et al. J Biol Chem, 1995, 270(23), 13585-13588.
[4] Alessandrini A, et al. Proc Natl Acad Sci U S A, 1999, 96(22), 12866-12869.
[5] Mandic A, et al. Melanoma Res, 2001, 11(1), 11-19.
[6] Hotokezaka H, et al. J Biol Chem, 2002, 277(49), 47366-47372.
[7] Clemons AP, et al. Pancreas, 2002, 25(3), 251-259.
[8] Zelivianski S, et al. Int J Cancer, 2003, 107(3), 478-485.
[9] Moon DO, et al. Int Immunopharmacol, 2007, 7(1), 36-45.
[10] Kojima K, et al. Cancer Res, 2007, 67(7), 3210-3219.
Sigma Aldrich - P215 external link
Biochem/physiol Actions
Specific inhibitor of the activation of mitogen-activated protein kinase kinase (MAPKK).
Legal Information
Sold with permission of Warner Lambert Company.

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