1148119-16-7

Basic information

• Product Name: (E)-6-fluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
• Synonyms: (E)-6-fluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
• CAS NO: 1148119-16-7
• Molecular Weight: 307.247
• Mol File: 1148119-16-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-6-fluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-6-fluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(1148119-16-7)
• EPA Substance Registry System: (E)-6-fluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(1148119-16-7)

Safety Data

• Hazardous Substances Data: 1148119-16-7(Hazardous Substances Data)

Upstream product

• 56341-39-0 6-fluoro-2-oxindole 
• 454-89-7 3-Trifluoromethylbenzaldehyde 

Relevant articles and documents

N'-Alkylaminosulfonyl Analogues of 6-Fluorobenzylideneindolinones with Desirable Physicochemical Profiles and Potent Growth Inhibitory Activities on Hepatocellular Carcinoma

The benzylideneindolinone 6-chloro-3-(3′-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (4) was reported to exhibit potent and selective growth inhibitory effects on hepatocellular carcinoma (HCC). Corroborative evidence supported multi-receptor tyrosine kinase (RTK) inhibition as a possible mode of action. However, the poor physicochemical properties of 4 limited its furtherance as a lead compound. In this study, the modification of 4 was investigated with the aim of improving its potency and physicochemical profile. The 6-fluorobenzylideneindolinone 3-12 bearing a 3′-N-propylaminosulfonyl substituent was found to be a promising substitute. Compound 3-12 [6-fluoro-3-(3′-N-propylaminosulfonylbenzylidene)-1,3-dihydroindol-2-one] was found to be tenfold more soluble than 4 and to have sub-micromolar growth inhibitory activities on HCC cells. It is apoptogenic and inhibits the phosphorylation of several RTKs in HuH7, of which the inhibition of FGFR4 and HER3 are prominent. Compound 3-12 decreased the tumor load in a physiologically relevant orthotopic HCC xenograft murine model. Structure-activity relationships support pivotal roles for the fluoro and N′-propylaminosulfonyl moieties in enhancing cell-based activity and moderating the physicochemical profile (solubility, permeability) of 3-12.

NOVEL BENZYLIDENE-INDOLINONE AND THEIR MEDICAL AND DIAGNOSTIC USES

The present invention relates generally to organic chemistry, biochemistry, pharmacology and medicine. More particularly, it relates to 3-benzylidene-indolin-2-one derivatives and their physiologically acceptable salts and prodrugs which modulate the activity of protein kinases ( PKs ), especially protein tyrosine kinase, and, therefore, are expected to exhibit a salutary effect against disorders related to abnormal PK activity. The present invention is further directed to methods of using of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of protein kinase-mediated diseases and disorders, such as cancer.