Chelerythrine

Base Information

• Chemical Name: Chelerythrine
• CAS No.: 34316-15-9
• Deprecated CAS: 11046-21-2
• Molecular Formula: C21H18NO4
• Molecular Weight: 348.378
• Hs Code.: 2933990090
• European Community (EC) Number: 251-930-0
• UNII: E3B045W6X0
• DSSTox Substance ID: DTXSID20861211
• Nikkaji Number: J19.428J
• Wikipedia: Chelerythrine
• Wikidata: Q5089853
• Pharos Ligand ID: YL1P3XUNMWM6
• Metabolomics Workbench ID: 67437
• ChEMBL ID: CHEMBL13045
• Mol file: 34316-15-9.mol

Synonyms:chelerythrine;chelerythrine chloride;chelerythrine hydroxide;chelerythrine sulfate;norchelerythrine

Chemical Property of Chelerythrine

Chemical Property:

• Melting Point: 195-205oC
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 496.37°C (rough estimate)
• PSA: 40.80000
• Density: 1.2985 (rough estimate)
• LogP: 0.72060
• Storage Temp.: Desiccate at -20°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slightly
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 348.12358306
• Heavy Atom Count: 26
• Complexity: 516

Purity/Quality:

Chelerythrine chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5
• Description: Chelerythrine chloride is the chloride form of Chelerythrine chloride which is a benzophenanthridine alkaloid isolated from the plant Chelidonium majus (greater celandine). It is a kind of potent, selective, and cell-permeable protein kinase C inhibitor, an efficient antagonist of G-protein-coupled CB1 receptors, and an independent activator of MAPK pathways. It has a wide range of biological activities including antiplatelet, anti-inflammatory, antibacterial and antitumor effects. It has reported of that it is capable of inducing apoptosis in HL-60 human promyelocytic leukemia cells and several other cancer cell lines. The underlying mechanism is through its effects of inhibiting the binding of BclXL to Bax or Bad.

Technology Process of Chelerythrine

There total 15 articles about Chelerythrine 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: 15.0%

allocryptopine N-oxide (87264-52-6) → chelerythrinium (34316-15-9) + C21H23NO6 (87264-54-8)

Guidance literature:

Irradiation;

Reference yield:

12,13-dihydrochelerythrine (6880-91-7) → chelerythrinium (34316-15-9)

Guidance literature:

With iodine; sodium acetate; In ethanol; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2016.04.059

Reference yield:

6-bromonaphtho[2,3-d][1,3]dioxol-5-ol (180411-11-4) → chelerythrinium (34316-15-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 0.25 h / 20 °C / Inert atmosphere

1.2: 5 h / 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

3.1: sodium hydroxide / water; methanol / 48 h / Inert atmosphere; Reflux

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 20 °C / Inert atmosphere

6.1: bis(pinacol)diborane; potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl sulfoxide / 16 h / Inert atmosphere

7.1: sodium acetate; iodine / ethanol / 2 h / Inert atmosphere; Reflux

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; iodine; potassium acetate; sodium acetate; sodium hydride; bis(pinacol)diborane; sodium hydroxide; In methanol; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: |Smiles Aromatic Rearrangement;

DOI:10.1016/j.bmc.2016.04.059

upstream raw materials:

allocryptopine N-oxide

6-bromonaphtho[2,3-d][1,3]dioxol-5-ol

12,13-dihydrochelerythrine

1,2-dimethoxybenzene

Downstream raw materials:

6-acetonyldihydrochelerythrine

oxychelerythrine

6-ethoxydihydrochelerythrine

6-methoxy-5,6-dihydrochelerythrine

Refernces

• 1、 Iwasa, Kinuko,Takao, Narao. "THE PYROLYSIS AND PHOTOLYSIS OF THE PROTOPINE TYPE ALKALOID N-OXIDES. THE SYNTHESIS OF THE SECOBERBINES AND BENZOPHENANTHRIDINES". . p. 1535 - 1539. Retrieved 2007/10/02.