6524-20-5

Basic information

• Product Name: 3-acetonylidene-2-oxindole
• Synonyms: 3-acetonylidene-2-oxindole;1,3-Dihydro-3-(2-oxopropylidene)-2H-indol-2-one
• CAS NO: 6524-20-5
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Mol File: 6524-20-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 428.4°C at 760 mmHg
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 1.52E-07mmHg at 25°C
• Refractive Index: 1.667
• CAS DataBase Reference: 3-acetonylidene-2-oxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetonylidene-2-oxindole(6524-20-5)
• EPA Substance Registry System: 3-acetonylidene-2-oxindole(6524-20-5)

Safety Data

• Hazardous Substances Data: 6524-20-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H9NO2/c1-7(13)6-9-8-4-2-3-5-10(8)12-11(9)14/h2-6H,1H3,(H,12,14)/b9-6-

Upstream product

• 91-56-5 indole-2,3-dione 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 1369310-49-5 C₁₉H₁₈N₂O₄ 
• 1369310-53-1 C₂₇H₂₄N₂O₆ 
• 1369310-55-3 C₂₄H₂₆N₂O₆ 
• 1369310-54-2 (1S,2S,3R,4S)-tert-butyl 4-hydroxy-4-methyl-3-nitro-2'-oxo-2-phenylspiro[cyclopentane-1,3'-indoline]-1'-carboxylate 
• 1369310-57-5 C₂₅H₂₈N₂O₆ 
• 1369310-32-6 1-carbobenzyloxy-3-(2-oxopropyl)indolin-2-one 
• 1369310-60-0 C₂₅H₂₈N₂O₇ 
• 1369310-62-2 C₂₄H₂₅BrN₂O₆ 
• 1369310-64-4 C₂₄H₂₄Cl₂N₂O₆ 
• 1369310-77-9 C₁₉H₁₈N₂O₄ 

Relevant articles and documents

1,3-CYCLOHEXANEDIONE DERIVATIVES AND 1,3-CYCLOPENTANEDIONE DERIVATIVES AS BUFFERING MOLECULES IN NON-AQUEOUS SOLUTIONS

This invention relates to 1,3-cyclohexanedione derivatives and 1,3-cyclopentanedione derivatives that have buffering function in non-aqueous solutions and to the use thereof for tuning the conditions to control chemical events in non-aqueous solutions. One aspect of the invention is a method for buffering a non-aqueous solution, including adding a buffering molecule to the non-aqueous solution, in which the non-aqueous solution contains an organic solvent, the buffering molecule is a 1,3-cyclohexanedione derivative or a 1,3-cyclopentanedione derivative, and the buffering molecule is optionally conjugated to a solid support.

Organocatalytic Aza-Michael/Michael Cyclization Cascade Reaction: Enantioselective Synthesis of Spiro-oxindole Piperidin-2-one Derivatives

A simple, direct, and highly enantioselective synthesis of spiro-oxindole piperidin-2-one derivatives was achieved through an aza-Michael/Michael cyclization cascade sequence using a squaramide catalyst. The desired products were obtained in excellent yields (up to 99%) and good to high stereoselectivities (up to >20:1 dr and up to 99% ee) under mild conditions.

Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1

Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.