1421507-39-2

Basic information

• Product Name: (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
• Synonyms: (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
• CAS NO: 1421507-39-2
• Molecular Weight: 325.238
• Mol File: 1421507-39-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(1421507-39-2)
• EPA Substance Registry System: (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one(1421507-39-2)

Safety Data

• Hazardous Substances Data: 1421507-39-2(Hazardous Substances Data)

Upstream product

• 3863-11-4 3,4-difluoroaniline 
• 76778-13-7 2-chloro-N-(3,4-difluorophenyl)acetamide 
• 100-52-7 benzaldehyde 
• 71294-07-0 5,6-difluoro-1,3-dihydro-indol-2-one 

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.