5654-97-7

Basic information

• Product Name: 1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE
• Synonyms: 1,3-Dihydropyrrolo[2,3-b]pyridine-2-one;1,3-Dihydropyrrolo[2,3-b]pyridin-2-one;1H,2H,3H-pyrrolo[2,3-b]pyridin-2-one;7-Azaoxindole, >=97%;1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE;2H-PYRROLO[2,3-B]PYRIDIN-2-ONE, 1,3-DIHYDRO-;7-azaoxindole;1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one
• CAS NO: 5654-97-7
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators;Heterocyclic Compounds
• Mol File: 5654-97-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 175 °C
• Boiling Point: 362.474 °C at 760 mmHg
• Flash Point: 173.019 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.42±0.20(Predicted)
• CAS DataBase Reference: 1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE(5654-97-7)
• EPA Substance Registry System: 1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE(5654-97-7)

Safety Data

• Hazardous Substances Data: 5654-97-7(Hazardous Substances Data)

Usage

Uses

1,3-DIHYDRO-2H-PYRROLO[2,3-B]PYRIDINE-2-ONE is used for preparation of 3-(anilinomethylene)oxindoles and analogs as protein tyrosine kinase and protein serine/threonine kinase inhibitors.

InChI:InChI=1/C7H6N2O/c10-6-4-5-2-1-3-8-7(5)9-6/h1-3H,4H2,(H,8,9,10)

Upstream product

• 101860-97-3 2-amino-3-pyridylacetic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 438210-61-8 1-(2-amino-[3]pyridyl)-2-diazo-ethanone 
• 1071087-00-7 3-(2-trimetylacetylamino)pyridylacetic acid 
• 6635-88-7 3-(cyanomethyl)pyridine 1-oxide 
• 101012-32-2 2-(2-chloropyridin-3-yl)acetonitrile 
• 113423-51-1 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one 
• 7440-66-6 zinc 
• 640735-25-7 4-fluoro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine 
• 13939-06-5 molybdenum hexacarbonyl 
• 7521-41-7 2-Aminonicotinaldehyde 
• 6959-48-4 3-chloromethylpyridinium chloride 
• 6443-85-2 3-pyridinylacetonitrile 
• 86847-66-7 2,2-dimethyl-N-(3-methylpyridin-2-yl)propionamide 

Downstream Products

• 126807-18-9 1H-pyrrolo[2,3-b]pyridine-2,3-dione-3-oxime 
• 885031-86-7 tert-butyl 2'-oxo-1',2'-dihydro-1H-spiro[piperidine-4,3'-pyrrolo[2.3-b]pyridine]-1-carboxylate 
• 156136-84-4 1-methyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 1375541-21-1 (S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid 
• 1192834-15-3 C₂₈H₂₉N₃O₃ 
• 1416438-78-2 spiro[cyclopropane-1,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 
• 879132-48-6 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 

Relevant articles and documents

Ambipolar organic field-effect transistors based on N-Unsubstituted thienoisoindigo derivatives

To investigate a hybrid of isoindigo and thienoisoindigo (TIIG), a new series of unsymmetrical TIIG analogs, in which one of the outer thiophene rings of TIIG is replaced by benzene (CS) or pyridine (NS) are prepared. In addition, the π-skeleton extension

7,7′-Diazaindirubin - A small molecule inhibitor of casein kinase 2 in vitro and in cells

Aza- and diaza-bisindoles were synthesized by coupling of 7-azaisatin, 7-azaoxindol, 7-azaindoxyl acetate, and their non-aza counterparts, respectively. Whereas 7,7′-diazaindigo (10) and 7,7′-diazaisoindigo (11) did not show antiproliferative activity in several human tumor cell lines up to 100 μM, 7-azaindirubin (12) and 7′-azaindirubin (13) were more active than the parent molecule, indirubin, in LXFL529L cells (human large cell lung tumor xenograft), and 7,7′-diazaindirubin (14) was exhibiting substantially enhanced growth inhibitory activity in these cells. In the NCI 60 cell line panel, 14 displayed antiproliferative activity preferentially in certain melanoma and non-small cell lung cancer cells. In contrast to the potent serine/threonine/tyrosine kinase inhibition observed for indirubins, kinase inhibition profiling of 14 in 220 kinases revealed largely a loss of kinase inhibitory activity towards most kinases, with retained inhibitory activity for just a few kinases. At 1 μM concentration, especially casein kinases CK1γ3, CK2α, CK2α2, and SIK were inhibited by more than 50%. In cell-based assays, 14 markedly affected CK2-mediated signaling in various human tumor cells. In MCF7 cells, 14 induced cell cycle arrest at G1 and G2/M and apoptosis, whereas CK2-deficient MCF7 cells were resistant. These findings reveal a novel key mechanism of action for 14, suggesting primarily CK2 inhibition to be causally related to growth inhibition of human tumor cells.

Synthesis and biological evaluation of 2-indolinone derivatives as potential antitumor agents

Three series of 3-substituted-indolin-2-ones and azaindolin-2-ones have been synthesized and showed potential antiproliferative activity to cancer cell lines. The inhibition activities on VEGF-induced VEGFR phosphorylation were observed for selected 2-indolinones. Among the compounds synthesized, 5-fluoroindolin-2-one derivative 23 with a pyridone unit showed the most significant enzymatic and cellular activities. Flow cytometric analysis indicates that 23 plays a role in suppressing HCT-116 cell proliferation via G1 phase arrest and apoptosis in a dose dependent manner. The binding mode of compound 23 complexed with VEGFR-2 was predicted using FlexX algorithm. Described here are the chemistry and biological testing for these series which will guide the design and optimization of novel 2-indolione antitumor agents.