251356-45-3

Basic information

• Product Name: SU 16f
• Synonyms: SU 16f;5-[1,2-Dihydro-2-oxo-6-phenyl-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-propanoicacid;(Z)-3-(2,4-Dimethyl-5-((2-oxo-6-phenylindolin-3-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid
• CAS NO: 251356-45-3
• Molecular Formula: C24H22N2O3
• Molecular Weight: 386.45
• EINECS: -0
• Product Categories: Angiogenesis and Metastasis
• Mol File: 251356-45-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 661.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.292±0.06 g/cm3(Predicted)
• Storage Temp.: Store at RT
• PKA: 4?+-.0.10(Predicted)
• CAS DataBase Reference: SU 16f(CAS DataBase Reference)
• NIST Chemistry Reference: SU 16f(251356-45-3)
• EPA Substance Registry System: SU 16f(251356-45-3)

Safety Data

• Hazardous Substances Data: 251356-45-3(Hazardous Substances Data)

Usage

Uses

SU 16f is used in the synthetic preparation of [(Dihydrooxoindolylidene)methyl]pyrrolepropanoic Acid as a tyrosine kinase inhibitor.

General Description

A cell-permeable indolinone compound that acts as a potent, ATP site-targeting PDGFR inhibitor (IC50 = 10 nM against PDGFRβ), while affecting Flk-1/KDR/ VEGFR2, FGFR1, and EGFR only at much higher concentrations (IC50 = 0.14, 2.29, and >100 μM, respectively). Reported to selectively inhibit PDGFβ- over EGF-stimulated proliferation in EGFR-expressing NIH 3T3 cultures (IC50 = 0.11 and 21.9 μM, respectively) and exhibit much weaker potency against the proliferation of HUVEC cells upon FGF or VEGF stimulation (IC50 = 10 μM).

Upstream product

• 17266-65-8 ethyl 4,6-dioxo-5-methylheptanoate 
• 54278-10-3 ethyl 5-(ethoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-propanoate 
• 54474-50-9 2,4-dimethyl-3-pyrrolepropanoic acid 
• 80726-56-3 2-nitro-4-phenylbenzeneacetic acid 
• 98-80-6 phenylboronic acid 
• 100487-83-0 dimethyl 3-nitrobiphenyl-4-malonate 
• 206879-57-4 4-Fluoro-3-nitrobiphenyl 
• 54474-51-0 methyl 2,4-dimethyl-3-pyrrolepropionate 
• 13219-76-6 4-<2-(methoxycarbonyl)ethyl>-3,5-dimethylpyrrole-2-carboxylic acid 
• 18818-25-2 methyl 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoate 
• 20303-31-5 benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 1133-96-6 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid 
• 90751-00-1 6-phenyl-2-oxindole 

Relevant articles and documents

FORMULATIONS FOR PHARMACEUTICAL AGENTS IONIZABLE AS FREE ACIDS OR FREE BASES

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Design, synthesis, and evaluations of substituted 3-[(3- or 4- carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases

Receptor tyrosine kinases (RTKs) have been implicated as therapeutic targets for the treatment of human diseases including cancers, inflammatory diseases, cardiovascular diseases including arterial restenosis, and fibrotic diseases of the lung, liver, and kidney. Three classes of 3-substituted indolin-2-ones containing propionic acid functionality attached to the pyrrole ring at the C-3 position of the core have been identified as catalytic inhibitors of the vascular endothelial growth factor (VEGF), fibroblast growth factor (FGF), and platelet-derived growth factor (PDGF) RTKs. Some of the compounds were found to inhibit the tyrosine kinase activity associated with isolated vascular endothelial growth factor receptor 2 (VEGF-R2) [fetal liver tyrosine kinase 1 (Flk-1)/kinase insert domain- containing receptor (KDR)], fibroblast growth factor receptor (FGF-R), and platelet-derived growth factor receptor (PDGF-R) tyrosine kinase with IC50 values at nanomolar level. Thus, compound 1 showed inhibition against VEGF-R2 (Flk-1/KDR) and FGF-R1 tyrosine kinase activity with IC50 values of 20 and 30 nM, respectively, while compound 16f inhibited the PDGF-R tyrosine kinase activity with IC50 value of 10 nM. Structural models and structure-activity relationship analysis of these compounds for the target receptors are discussed. The cellular activities of these compounds were profiled using cellular proliferation assays as measured by bromodeoxyuridine (BrdU) incorporation. Specific and potent inhibition of cell growth was observed for some of these compounds. These data provide evidence that these compounds can be used to inhibit the function of these target receptors.