2-Pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one

Base Information

• Chemical Name: 2-Pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one
• CAS No.: 845714-00-3
• Molecular Formula: C₁₂H₁₁N₃O
• Molecular Weight: 213.239
• Hs Code.: 2933990090
• UNII: 5M2GUN688C
• ChEMBL ID: CHEMBL225519
• DSSTox Substance ID: DTXSID50471069
• Nikkaji Number: J2.603.815D
• Wikidata: Q27076833
• Mol file: 845714-00-3.mol

Synonyms:PHA 767491;PHA-767491;PHA767491

Chemical Property of 2-Pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one

Chemical Property:

• Vapor Pressure: 2.51E-15mmHg at 25°C
• Boiling Point: 620.6°C at 760 mmHg
• Flash Point: 329.1°C
• PSA: 57.78000
• Density: 1.287
• LogP: 2.49340
• Storage Temp.: Desiccate at RT
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥10.65 mg/mL in DMSO
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 213.090211983
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98% min ^*data from raw suppliers

PHA 767491 hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(=O)C2=C1NC(=C2)C3=CC=NC=C3
• Uses: Cdc7 kinase is a key regulator of the S-phase of the cell cycle. It is known to promote the activity of DNA replication origins in eukaryotic organisms. Inhibition of Cdc7 kinase causes blockade of DNA synthesis in human cell lines. Tumor cells are then funneled into the apoptotic pathway in a p53-independent manner. Pharmacological inhibition of Cdc7 kinase can be an effective strategy for the development of oncologic therapeutics useful for treatment of cancers. PHA 767491 HYDROCHLORIDE is a potent inhibitor of Cdc7 kinase with an IC50 value of 10 nM in the presence of 1.5 μM ATP. At 10 μM, PHA 767491 HYDROCHLORIDE induces apoptotic cell death in multiple cancer cell types. PHA 767491 HYDROCHLORIDE also inhibits Cdk9, a kinase involved in the phosphorylation of RNA polymerase II and in transcriptional regulation of gene expression, with an IC50 value of 34 nM.[Cayman Chemical] PHA 767491 is a potent and selective ATP-competitive dual inhibitor cdc7/cdk9. It blocks DNA synthesis and affects the phosphorylation of the replicative DNA helicase at Cdc7-dependent phosphorylation sites. Inhibits cell proliferation in a variety of human cell lines and induces apoptosis in a p53-independent manner in vivo. Also inhibits mitogen-activated protein kinase-activated protein kinase-2 (MK-2).

Technology Process of 2-Pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one

There total 3 articles about 2-Pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-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: 41.1%

2-(bromoacetyl)pyridine hydrobromide (17570-98-8) + piperidine-2,4-dione (50607-30-2) → PHA-767491 (845714-00-3)

Guidance literature:

2-(bromoacetyl)pyridine hydrobromide; piperidine-2,4-dione; With ammonium acetate; In ethanol; at 20 ℃;

With hydrogenchloride; methanol; In 1,4-dioxane; for 0.5h;

Reference yield: 37.0%

4-bromoacetylpyridine hydrobromide (5349-17-7) + piperidine-2,4-dione (50607-30-2) → PHA-767491 (845714-00-3)

Guidance literature:

With ammonium acetate; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2022.128588

Reference yield:

2-[3-(ethoxycarbonyl)-5-pyridin-4-yl-1H-pyrrol-2-yl]ethanaminium chloride (845538-60-5) → PHA-767491 (845714-00-3)

Guidance literature:

With potassium carbonate; In ethanol; for 16h; Heating / reflux;

upstream raw materials:

2-[3-(ethoxycarbonyl)-5-pyridin-4-yl-1H-pyrrol-2-yl]ethanaminium chloride

4-bromoacetylpyridine hydrobromide

piperidine-2,4-dione

2-(bromoacetyl)pyridine hydrobromide

Refernces

• 1、 Anderson, David R.,Meyers, Marvin J.,Vernier, William F.,Mahoney, Matthew W.,Kurumbail, Ravi G.,Caspers, Nicole,Poda, Gennadiy I.,Schindler, John F.,Reitz, David B.,Mourey, Robert J.. "Pyrrolopyridine inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)". . p. 2647 - 2654. Retrieved 2008/02/04.
• 2、 -. "PYRIDYLPYRROLE DERIVATIVES ACTIVE AS KINASE INHIBITORS". Page/Page column 32. . Retrieved 2010/02/10.