Damnacanthal

Base Information

• Chemical Name: Damnacanthal
• CAS No.: 477-84-9
• Molecular Formula: C16H10 O5
• Molecular Weight: 282.252
• European Community (EC) Number: 683-107-0
• UNII: WUC3CB63CD
• DSSTox Substance ID: DTXSID10197253
• Nikkaji Number: J12.603I
• Wikipedia: Damnacanthal
• Wikidata: Q5212724
• NCI Thesaurus Code: C1480
• Pharos Ligand ID: MR4M5PA3WD4Q
• Metabolomics Workbench ID: 126902
• ChEMBL ID: CHEMBL212948
• Mol file: 477-84-9.mol

Synonyms:damnacanthal

Chemical Property of Damnacanthal

Chemical Property:

• Vapor Pressure: 6.29E-12mmHg at 25°C
• Melting Point: 218～219℃
• Boiling Point: 531.9°Cat760mmHg
• PKA: 5.26±0.20(Predicted)
• Flash Point: 204.9°C
• PSA: 80.67000
• Density: 1.461g/cm³
• LogP: 1.98870
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 7 mg/ml)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 282.05282342
• Heavy Atom Count: 21
• Complexity: 460

Purity/Quality:

98%Min ^*data from raw suppliers

Damnacanthal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O
• Description: Damnacanthal (477-84-9) is a potent inhibitor of p56lck?tyrosine kinase activity (IC50?= 17 nM for inhibition of autophosphorylation). Displays 7- to 20-fold selectivity over p59fyn?and p60src?tyrosine kinases and > 40-fold to 100-fold selectivity over other kinases.1?Mobilizes intracellular Ca2+?in dermal fibroblasts.2?Inhibits LIM-kinase, impairing cell migration and invasion.3?A potent inhibitor of angiogenesis.4?Inhibits mast cell activation.5
• Uses: Damnacanthal-induced anti-inflammation is associated with inhibition of NF-κB activity. Damnacanthal is used in the treatment of inflammatory-related diseases.

Technology Process of Damnacanthal

There total 1 articles about Damnacanthal 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:

phthalic anhydride (85-44-9) → damnacanthal (477-84-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aluminum (III) chloride; sodium chloride / 0.75 h / 165 - 170 °C

2.1: potassium carbonate / acetone / 20 h / 20 °C

3.1: potassium carbonate / acetone / 22 h / Reflux

4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux

5.1: sodium hydroxide / water / 24 h / 20 °C

6.1: potassium carbonate / acetone / 20 h / 20 °C

7.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 24 h / Reflux

7.2: 24 h / Reflux

With aluminum (III) chloride; N-Bromosuccinimide; potassium carbonate; sodium chloride; sodium hydroxide; dibenzoyl peroxide; In tetrachloromethane; water; acetone; 1.1: |Friedel-Crafts Acylation;

DOI:10.1007/s00044-012-0197-5

Reference yield:

damnacanthal (477-84-9) → nordamnacanthal (3736-59-2)

Guidance literature:

With 1,4-dioxane; aluminium trichloride;

Reference yield:

damnacanthal (477-84-9) → damnacanthol (477-83-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; Product distribution;

DOI:10.1248/bpb.21.641

upstream raw materials:

phthalic anhydride

Downstream raw materials:

nordamnacanthal

damnacanthol

Refernces

• 1、 Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu. "Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues". . p. 10042 - 10055. Retrieved 2013/09/23.