141210-63-1

Basic information

• Product Name: 3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE
• Synonyms: 3-[(DIMETHYLAMINO)METHYLENE]-1,3-DIHYDRO-2H-INDOL-2-ONE;3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE;(3Z)-3-[(Dimethylamino)methylene]-1,3-dihydro-2H-indol-2-one;(3Z)-3-(dimethylaminomethylene)-2-indolinone;(3Z)-3-(dimethylaminomethylene)indolin-2-one;(3Z)-3-(dimethylaminomethylene)oxindole;(3Z)-3-(dimethylaminomethylidene)-1H-indol-2-one;2H-976
• CAS NO: 141210-63-1
• Molecular Formula: C₁₁H₁₂N₂O
• Molecular Weight: 188.23
• Mol File: 141210-63-1.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE(141210-63-1)
• EPA Substance Registry System: 3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE(141210-63-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 141210-63-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Dimethylaminomethylene-1,3-dihydro-indol-2-one is used as an intermediate in the synthesis of T294270, a derivative of H957770. H957770 is a carcinogen utilized in the study of intestinal bacteria metabolism, which can provide insights into the development of new drugs and therapies targeting cancer and other related diseases.
Used in Chemical Research:
3-DIMETHYLAMINOMETHYLENE-1,3-DIHYDRO-INDOL-2-ONE is also used as a research tool in the field of chemical synthesis, particularly for the development of new methodologies and techniques. Its reactivity and structural features make it an attractive candidate for exploring novel synthetic pathways and understanding the underlying chemical reactions.
Used in Food Industry:
3-Dimethylaminomethylene-1,3-dihydro-indol-2-one is created through the heat processing of food, which suggests that it may have potential applications in the food industry. It could be used to study the effects of heat processing on food chemistry and to develop new methods for improving the quality, safety, and nutritional value of processed foods.

Upstream product

• 59-48-3 2-oxoindole 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 57315-91-0 3-Dimethylaminomethylene-2,3-dihydro-1H-indol-2-one 

Downstream Products

• 91505-98-5 1-(3-Methoxyphenyl)-3-(dimethylaminomethylene)-2(1H,3H)-indolone 
• 159212-33-6 3-[1-(2-Phenyl-propylamino)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 159212-33-6 3-[1-(2-Phenyl-propylamino)-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 
• 159212-34-7 3-(phenethylamino-methylene)-indolin-2-one 
• 159212-35-8 3-[1-Phenethylamino-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 

Relevant articles and documents

Rationally derived inhibitors of hepatitis c virus (Hcv) p7 channel activity reveal prospect for bimodal antiviral therapy

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Design, synthesis and preliminary biological evaluation of novel benzyl sulfoxide 2-indolinone derivatives as anticancer agents

In this work, a series of novel benzyl sulfoxide 2-indolinone derivatives was designed and synthesized as potent anticancer agents. Tyrosine kinase inhibitory activity assay indicated that most of the compounds showed significant activity. The in vitro antiproliferative activity of these compounds was further investigated against five human cancer cell lines (HeLa, HepG2, MCF-7, SCC-15, and A549). Several compounds exhibited evident activities. Among them, (Z)-3-(((4-bromobenzyl)sulfinyl)methylene)indolin-2-one (6j) and (Z)-3-((benzylsulfinyl) methylene)-5-bromoindolin-2-one (6o) were found to be effective tyrosine kinase inhibitors (IC50 = 1.34 and 2.69 μM, respectively) in addition to having noteworthy antitumor potential (the average IC50 value of 6j or 6o was less than 40 μM). This class of novel derivatives has promising potential for further development as anticancer agents.

Alpha carbolines and uses thereof

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LACTAM AND AMIDE ACETALS. 69. SYNTHESIS AND PROPERTIES OF 3-(AMINOMETHYLENE)-2-INDOLINONE DERIVATIVES

Oxindole derivatives reacted with the diethyl acetals of dimethylformamide and dimethylacetamide to give the corresponding derivatives of 3-(aminomethylene)-, (aminoethylidene)-, and (ethoxyethylidene)-2-indolinone.These products were then easily converted to N-aryl- and N-alkylaminomethyleneoxindoles upon treatment with aryl or alkyl amines.The alkylation of N,N-dimethylaminomethylene-2-indolinones by dimethyl sulfate and triethyloxonium tetrafluoroborate, and the reactions of the resulting methyl sulfates and tetrafluoroborates with nucleophilic reagents were studied.The configuration of the 3-(aminomethylene)-2-indolinone derivatives prepared at the enamine C=C double bond was investigated by NMR.The free energies of activation for the cis-trans isomerization were determined in a number of cases.

A Novel Class of "GABAergic" Agents: 1-Aryl-3-(aminoalkylidene)oxindoles

Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles.Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)ethylidene and N-methyl-2-pyrrolidinylidene side chains.The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels.Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid.Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.

Heteroylidene indolone compounds

Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.