Alsterpaullone

Base Information

• Chemical Name: Alsterpaullone
• CAS No.: 237430-03-4
• Molecular Formula: C₁₆H₁₁N₃O₃
• Molecular Weight: 293.282
• Hs Code.: 2933990090
• European Community (EC) Number: 636-614-6
• ChEMBL ID: CHEMBL50894
• DSSTox Substance ID: DTXSID50407444
• Metabolomics Workbench ID: 148493
• Nikkaji Number: J1.159.197C
• NSC Number: 705701
• Pharos Ligand ID: JY8BJBJJAVCW
• Wikidata: Q27074414
• Mol file: 237430-03-4.mol

Synonyms:9-nitro-7,12-dihydroindolo(3,2-d)(1)benzazepin-6(5H)-one;alsterpaullone

Chemical Property of Alsterpaullone

Chemical Property:

• Vapor Pressure: 7.4E-17mmHg at 25°C
• Melting Point: >330℃
• Refractive Index: 1.737
• Boiling Point: 651.5 °C at 760 mmHg
• PKA: 14.18±0.20(Predicted)
• Flash Point: 347.8 °C
• PSA: 90.71000
• Density: 1.461 g/cm³
• LogP: 3.89890
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 293.08004122
• Heavy Atom Count: 22
• Complexity: 478

Purity/Quality:

98%,99%, ^*data from raw suppliers

Alsterpaullone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C3=CC=CC=C3NC1=O)NC4=C2C=C(C=C4)[N+](=O)[O-]
• Description: Alsterpaullone (237430-03-4) is a potent and selective inhibitor of GSK-3β and CDK5/p25. Potent inhibitor of CDK1/cyclin B (IC50 = 35 nM).1?Alsterpaullone induces apoptosis2 and inhibits angiogenesis3.
• Uses: Alsterpaullone is a potent glycogen synthase kinase-3 inhibitor and a potential therapeutic agents for treatment of Parkinson disease. Alsterpaullone is a derivative of kenpaullone , an ATP-competitive inhibitor of several cyclin-dependent kinases (CDKs) as well as glycogen synthase kinase 3β (GSK3β). With slightly improved potency over kenpaullone, alsterpaullone selectively inhibits Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, Cdk5/p25, and GSK3α/β with IC50 values of 35, 15, 200, 40, and 4 nM, respectively. Alsterpaullone has been used to inhibit the cytosolic degradation of β-catenin to alter the canonical Wnt signaling pathway in primary axis patterning, to reduce tau phosphorylation in an effort to modify neuropathological events associated with Alzheimer’s disease, and to alter cell proliferation or protein expression in various diseases. Alsterpaullone has been used to stabilize β-catenin.

Technology Process of Alsterpaullone

There total 2 articles about Alsterpaullone 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: 33.0%

1H-[1]benzazepin-2,5(3H,4H)-dione (16511-38-9) + 4-nitrophenylhydrazine hydrochloride (636-99-7) → alsterpaullone (237430-03-4)

Guidance literature:

With sulfuric acid; sodium acetate; In acetic acid;

Reference yield:

5-[(4-nitro-phenyl)-hydrazono]-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → alsterpaullone (237430-03-4)

Guidance literature:

With sulfuric acid; acetic acid; at 70 ℃; for 3h; Yield given;

DOI:10.1021/jm9900570

upstream raw materials:

1H-[1]benzazepin-2,5(3H,4H)-dione

4-nitrophenylhydrazine hydrochloride

Refernces

• 1、 Schultz, Christiane,Link, Andreas,Leost, Maryse,Zaharevitz, Daniel W.,Gussio, Rick,Sausville, Edward A.,Meijer, Laurent,Kunick, Conrad. "Paullones, a series of cyclin-dependent kinase inhibitors: Synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity". . p. 2909 - 2919. Retrieved 2007/10/03.