20870-89-7

Usage

Chemical structure

A nitro-substituted indolinone derivative

Physical form

Yellow crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Uses

Precursor in the synthesis of other organic compounds, building block in pharmaceuticals and agrochemicals development, potential biological activity, valuable tool in medicinal chemistry and drug discovery, possible applications in dyes and pigments development.

Upstream product

• 14092-14-9 4-(methylamino)-3-penten-2-one 
• 2653-16-9 2-chloro-N-methyl-N-(4-nitrophenyl)acetamide 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 23543-31-9 2-bromo-N-methyl-N-(4-nitrophenyl)acetamide 
• 100-15-2 N-methyl(p-nitroaniline) 
• 61-70-1 N-methyl-2-indolinone 

Downstream Products

• 3484-32-0 1-methyl-5-nitro-1H-indole-2,3-dione 
• 156136-71-9 1-methyl-5-nitro-2-indolinethione 
• 20870-91-1 5-amino-1-methyl-1,3-dihydro-2H-indol-2-one 
• 110440-71-6 3-(4-diethylamino-phenylimino)-1-methyl-5-nitro-indolin-2-one 
• 1026814-21-0 1-Methyl-5-nitro-2-thioxo-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 

Relevant academic research and scientific papers

Synthesis of C-5 Benzoyl and Azido Functionalized 2,2′-Dithiobisand 2,2′-Diselenobis(1H-indoles)

Novel methods for the synthesis of C-5 benzoyl and azido analogues of 2,2′-dithiobis(1H-indole), 1, and 2,2′-diselenobis(1H-indole), 2, are described to further explore the structure activity relationships in this region of the molecule. Analogues 3-6 dis

MODULATORS OF COMPLEX I

The present invention describes compounds modulating the function of mitochondrial complex I (NADH-quinone oxidoreductase) having formula (I)

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation

A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (Hetero)aryl bromides: Efficient and complementary approach to 3-acyl-2-oxindoles

An efficient Pd-catalyzed carbonylative α-arylation of 2-oxindoles with aryl and heteroaryl bromides for the one-step synthesis of 3-acyl-2-oxindoles has been developed. This reaction proceeds efficiently under mild conditions and is complementary to the

Synthesis of spiro[furan-3,3′-indolin]-2′-ones by PET-catalyzed [3+2] reactions of spiro[indoline-3,2′-oxiran]-2-ones with electron-rich olefins

An efficient procedure for the synthesis of spiro[furan-3,3′-indolin] -2-ones and dispiro[cycloalkane-1,2′-furan-3′,3″-indolin]- 2″-ones has been achieved in high yields and stereoselectivity by photoinduced electron transfer-catalyzed [3+2] reactions of substituted spiro[indoline-3,2′-oxiran]-2-ones with olefins. The reactions proceed by ring opening of spiro[indoline-3,2′-oxiran]-2-ones via C β-O bond cleavage and subsequent cycloaddition with olefins by using 2,4,6-triphenylpyrylium tetarfluoroborate (TPT) as a sensitizer.

Irreversible Nek2 kinase inhibitors with cellular activity

A structure-based approach was used to design irreversible, cysteine-targeted inhibitors of the human centrosomal kinase, Nek2. Potent inhibition of Nek2 kinase activity in biochemical and cell-based assays required a noncatalytic cysteine residue (Cys22), located near the glycine-rich loop in a subset of human kinases. Elaboration of an oxindole scaffold led to our most selective compound, oxindole propynamide 16 (JH295). Propynamide 16 irreversibly inhibited cellular Nek2 without affecting the mitotic kinases, Cdk1, Aurora B, or Plk1. Moreover, 16 did not perturb bipolar spindle assembly or the spindle assembly checkpoint. To our knowledge, 16 is the first small molecule shown to inactivate Nek2 kinase activity in cells.

SUBSTITUTED ARYLSULFONYLAMINOMETHYLPHOSPHONIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF TYPE I AND II DIABETES MELLITUS

The present invention relates to substituted arylsulphonylaminomethylphosphonic acid derivatives of general formula (I) wherein R, X, Y and Z are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures thereof and salts thereof which ha

INHIBITORS OF FOCAL ADHESION KINASE

The invention provides inhibitors of focal adhesion kinase, an enzyme involved in the attachment of the cytoskeleton of a cell to an extracellular matrix, which has been implicated in processes such as cell migration, cell proliferation, and cell survival. The inhibitors are derivatives of a 5-substituted 2,4-diaminopyridine wherein the substituents are as defined herein. The invention also provides a method of using the inhibitors in treatment of cancer, and methods of preparation of the inhibitors by use of coupling reactions.

Oxazolidinones containing oxindoles as antibacterial agents

The present invention relates to novel oxazolidinones derivatives of oxindoles of formula I, or a pharmaceutically acceptable salt thereof wherein Y1 is —CH— or —CF—; R1 is —C1-4alkyl, optionally substituted with a fluoro atom, or R1 is —C3-5cycloalkyl; and R2 is —H or —CH3. These compounds are useful as antibacterial agents.