Aaptamine

Base Information

• Chemical Name: Aaptamine
• CAS No.: 85547-22-4
• Molecular Formula: C13H12N2O2
• Molecular Weight: 228.25
• Hs Code.: 2933990090
• UNII: FGW9D01COE
• DSSTox Substance ID: DTXSID201006106
• Nikkaji Number: J33.370K
• Wikidata: Q5682186
• ChEMBL ID: CHEMBL234658
• Mol file: 85547-22-4.mol

Synonyms:2-methoxy-3-oxoaaptamine;8,9-dimethoxy-1H-benzo(de)(1,6)naphthyridine;aaptamine

Chemical Property of Aaptamine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 420.578°C at 760 mmHg
• Flash Point: 208.158°C
• PSA: 47.14000
• Density: 1.246g/cm³
• LogP: 2.73330
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 228.089877630
• Heavy Atom Count: 17
• Complexity: 308

Purity/Quality:

98%Min ^*data from raw suppliers

Aaptamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C2=NC=CC3=C2C(=C1)C=CN3)OC
• Uses: Aaptamine is a spongean alkaloid that can activate the p21 promoter in the absence of p53 and can function as a proteasome inhibitor.

Technology Process of Aaptamine

There total 19 articles about Aaptamine 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: 89.0%

1-(6,7-Dimethoxy-8-nitro-1-isoquinolyl)-2-nitroethene (132213-53-7) → aaptamine (85547-22-4)

Guidance literature:

With iron; In ethanol; acetic acid; Ambient temperature; 1.) 2 h at room temperature,2.) 0.75 at 80-90 grad C;

DOI:10.1039/P19900003193

Reference yield: 84.0%

6,7-dimethoxy-8-nitro-1-vinylisoquinoline → aaptamine (85547-22-4)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); 1,10-Phenanthroline; molybdenum hexacarbonyl; In N,N-dimethyl-formamide; at 120 ℃; for 4h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00183

Reference yield: 60.0%

8,9-dimethoxy-2,3,3a,4,5,6-hexahydro-1H-benzo<1,6>naphthyridine (96838-35-6) → aaptamine (85547-22-4)

Guidance literature:

palladium on activated charcoal; In xylene; Heating;

DOI:10.1016/S0040-4039(00)94864-0

upstream raw materials:

1-(6,7-Dimethoxy-8-nitro-1-isoquinolyl)-2-nitroethene

8,9-dimethoxy-2,3,3a,4,5,6-hexahydro-1H-benzo<1,6>naphthyridine

6,7-dimethoxy-3,4-dihydro-isoquinoline

3,4-dihydro-7-hydroxy-6-methoxy-isoquinoline

Refernces

• 1、 Bassoli, Angela,Maddinelli, Giuseppe,Rindone, Bruno,Tollari, Stefano,Chioccara, Francesco. "A Simple Synthesis of Aaptamine, a 1H-Benzo-naphthyridine Alkaloid". . p. 150 - 151. Retrieved 1987.
• 2、 -. "AAPTAMINE ALKALOID DERIVATIVES AND SYNTHESIS METHOD AND APPLICATION THEREOF". . . Retrieved 2019/12/01.
• 3、 Pelletier, Jeffrey C.,Cava, Michael P.. "Synthesis of the Marine Alkaloids Aaptamine and Demethyloxyaaptamine and of the Parent Structure Didemethoxyaaptamine". . p. 616 - 622. Retrieved 2007/10/02.