1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Base Information

• Chemical Name: 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one
• CAS No.: 5654-97-7
• Molecular Formula: C7H6 N2 O
• Molecular Weight: 134.137
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10551472
• Nikkaji Number: J81.071A
• Wikidata: Q72444339
• Mol file: 5654-97-7.mol

Synonyms:5654-97-7;1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one;1H-pyrrolo[2,3-b]pyridin-2(3H)-one;7-AZAOXINDOLE;1,3-dihydropyrrolo[2,3-b]pyridin-2-one;1,3-Dihydro-2H-pyrrolo[2,3-b]pyridine-2-one;1H,2H,3H-pyrrolo[2,3-b]pyridin-2-one;MFCD07367951;1,3-Dihydro-2H-pyrrolo[2.3-b]pyridine-2-one;1,3-dihydro-2h-pyrrolo(2,3-b)pyridin-2-one;Silvercarbonate;2H-PYRROLO[2,3-B]PYRIDIN-2-ONE, 1,3-DIHYDRO-;7-AZA-2-OXINDOLE;1,3-DIHYDROPYRROLO[2,3-B]PYRIDINE-2-ONE;SCHEMBL578594;DTXSID10551472;ZXSQEZNORDWBGZ-UHFFFAOYSA-N;AKOS006287010;AC-5052;CS-W019704;PB29419;SY008090;1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one;AM20061330;1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one;A831090;J-504754;1 pound not3-DIHYDRO-2H-PYRROLO[2 pound not3-B]PYRIDINE-2-ONE

Chemical Property of 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.594
• Boiling Point: 362.474 °C at 760 mmHg
• PKA: 3.42±0.20(Predicted)
• Flash Point: 173.019 °C
• PSA: 41.99000
• Density: 1.286 g/cm³
• LogP: 0.71420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

98% ^*data from raw suppliers

7-Azaoxindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(NC1=O)N=CC=C2
• General Description: 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (7-azaoxindole) was evaluated as a potential antibacterial agent targeting thymidylate monophosphate kinase (TMPK) but exhibited low inhibitory activity (IC50 = 83 μM) and no antimicrobial effects against *E. coli* or *S. aureus*, likely due to poor cell permeability. While structurally related imidazopyridinones showed stronger TMPK inhibition, the 7-azaoxindole scaffold may require further optimization for therapeutic applications.

Technology Process of 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

There total 27 articles about 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one (113423-51-1) → 7-azaoxindole (5654-97-7)

Guidance literature:

With acetic acid; zinc; In acetonitrile;

Reference yield: 83.0%

C13H14N4O2S + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 7-azaoxindole (5654-97-7)

Guidance literature:

With tetraethylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; at 20 - 110 ℃; for 1h;

DOI:10.1016/j.tetlet.2015.09.123

Reference yield: 70.0%

1-Morpholin-4-yl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (205323-23-5) → 7-azaoxindole (5654-97-7)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -78 - -58 ℃;

DOI:10.1002/jhet.5570350127

upstream raw materials:

2-amino-3-pyridylacetic acid

N,N-dimethyl-aniline

1-(2-amino-[3]pyridyl)-2-diazo-ethanone

3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]-pyridin-2-one

Downstream raw materials:

1H-pyrrolo[2,3-b]pyridine-2,3-dione-3-oxime

1,3-dihydro-3,3-dimethyl-2H-pyrrolo<2,3-b>pyridin-2-one

4-{[(2-Oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide

1-methyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Refernces

Discovery of potent and orally active p53-MDM2 inhibitors RO5353 and RO2468 for potential clinical development

10.1021/ml400359z

The research aims to develop small-molecule MDM2 inhibitors to restore dysfunctional p53 activities for cancer treatment. The study builds on previous work on a non-imidazoline MDM2 inhibitor, RG7388, and explores additional derivatives to expand chemodiversity and identify potent and selective MDM2 antagonists with desirable pharmacological properties. The researchers focused on bioisosteric replacements of the 6-chlorooxindole group in RO8994, leading to the identification of two highly potent, selective, and orally active p53-MDM2 inhibitors, RO2468 and RO5353. These compounds demonstrated excellent in vitro and in vivo pharmacokinetic profiles and significant tumor regression in mouse models at doses comparable to RO8994. The key chemicals used in the research include RO8994, RO2468 (14), and RO5353 (16), along with various analogues such as 4-azaoxindole (I), 5-azaoxindole (II), 7-azaoxindole (III), 2-chloropyrrolo[2,3-d]pyrimidin-6-one (IV), and 2-chlorothienyl[3,2-b]pyrrol-5-one (V). The study concludes that RO2468 and RO5353 have promising potential for clinical development.

Synthetic Strategies towards Imidazopyridinones and 7-Azaoxindoles and their Evaluation as Antibacterial Agents

10.1002/ejoc.202100172

The research aims to develop new antimicrobial agents targeting thymidylate monophosphate kinase (TMPK), an enzyme essential for DNA synthesis in bacteria. The study explores the synthesis of imidazopyridinones and 7-azaoxindoles, two heterocyclic compounds with limited previous use in medicinal chemistry, to identify robust and safe synthetic methods for these potential inhibitors. The imidazopyridinones were found to be potent inhibitors of E. coli TMPK, with compound 1 showing an IC50 value of 1.4 μM and compound 2 having an IC50 of 5.6 μM. However, the 7-azaoxindole (compound 3) exhibited low activity with an IC50 of 83 μM. Despite their enzymatic activity, none of the compounds showed antimicrobial activity against E. coli or S. aureus cultures, likely due to poor cell wall penetration. The study concludes that while the imidazopyridinones are effective TMPK inhibitors, further research is needed to improve cell membrane permeability and explore alternative applications for the 7-azaoxindole class.

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