902757-75-9

Upstream product

• 928782-97-2 4-chloro-2-(phenylethynyl)aniline 
• 201230-82-2 carbon monoxide 
• 53691-91-1 N-(4-chlorophenyl)-3-phenylacrylamide 
• 17630-75-0 5-chloro-indolin-2-one 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 17630-76-1 5-chloroindole 2,3-dione 

Downstream Products

• 1194653-84-3 (2S,6S)-5'-chloro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 1194654-01-7 (1R,2R,5S,6S)-5'-chloro-5-methyl-2'-oxo-2,6-diphenylspiro[cyclohex[3]ene-1,3'-indoline]-3-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.

(E)-3-(Aryl(arylamino)methylene)indolin-2-one derivatives: An efficient synthetic approach and evaluation of their cancer inhibitory activity

A series of (E)-3-(aryl(arylamino)methylene)indolin-2-one derivatives were synthesised using an efficient synthetic approach. The method involved reaction of 3-bromo-3-(bromo(aryl)methyl)indolin-2-one with substituted anilines through nucleophilic substitution and a simultaneous elimination using NaHCO3 in DMF. The anticancer activity of the products against four cell lines, HCT-116, A549, SKOV3 and MDA-MB-231, was also evaluated, and several compounds showed moderate inhibitory activity.

3-substituted arylcarbonylindol-2-ketone and preparation method thereof

The invention relates to 3-substituted arylcarbonylindol-2-ketone and a preparation method thereof. According to the preparation method, indole-2-ketone and aromatic aldehyde are taken as raw materials, and a 3-substituted arylcarbonylindol-2-ketone compound with moderate-good yield is obtained through catalytic synthesis of inorganic salt under a mild condition. The preparation method has the characteristics of being quick in reaction speed, mild in reaction conditions, simple and convenient to operate and the like.

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.

BENZYLIDENE-INDOLINONE COMPOUNDS AND THEIR MEDICAL USE

Compounds of general formula I: wherein R1a, R1b, R2, R3a, R3b and X are as defined herein are tyrosine kinase inhibitors and are useful for the treatment of various diseases and conditions, for examp

Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation

A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.

Heterobimetallic cobalt/rhodium nanoparticle-catalyzed carbonylative cycloaddition of 2-alkynylanilines to oxindoles

(Chemical Equation Presented) The cobalt-rhodium heterobimetallic nanoparticle-catalyzed synthesis of oxindoles from 2-alkynylanilines in the presence of carbon monoxide is described.

Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2

A series of heterocycle-containing oxindoles was synthesized and their HIV antiviral activities were assessed. Some of these analogs exhibited potent inhibitory activities against both wild-type virus and a number of drug-resistant mutant viruses. In addi

NOVEL THERAPEUTIC USE OF INDOLINONE DERIVATIVES

Certain oxindole compounds have been found to be effective in experimentally induced autoimmune encephalitis and are therefore suggested for the preparation of a medicament for the prevention, treatment or amelioration of multiple sclerosis, or to delay the onset of or reduce the relapse rate in multiple sclerosis.