Canertinib

Base Information

• Chemical Name: Canertinib
• CAS No.: 267243-28-7
• Molecular Formula: C₂₄H₂₅ClFN₅O₃
• Molecular Weight: 485.946
• UNII: C78W1K5ASF
• DSSTox Substance ID: DTXSID8048943
• Nikkaji Number: J1.314.856B
• Wikipedia: Canertinib
• Wikidata: Q5032274
• NCI Thesaurus Code: C77588
• Pharos Ligand ID: T4U2H5D98F6F
• Metabolomics Workbench ID: 61631
• ChEMBL ID: CHEMBL31965
• Mol file: 267243-28-7.mol

Synonyms:Canertinib;CI 1033;CI-1033;CI1033

Chemical Property of Canertinib

Chemical Property:

• Appearance/Colour: white or similar to white crystalline powder
• Vapor Pressure: 2.86E-18mmHg at 25°C
• Melting Point: 188-190°
• Refractive Index: 1.659
• Boiling Point: 691 °C at 760 mmHg
• PKA: 12.09±0.43(Predicted)
• Flash Point: 371.7 °C
• PSA: 88.61000
• Density: 1.355 g/cm³
• LogP: 4.47540
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: insoluble in H2O; ≥10.1 mg/mL in EtOH; ≥12.15 mg/mL in DMSO with gentle warming
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 485.1629955
• Heavy Atom Count: 34
• Complexity: 671

Purity/Quality:

97% ^*data from raw suppliers

Canertinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
• Recent ClinicalTrials: A Phase II Study of CI-1033 in Treating Patients With Metastatic (Stage IV) Breast Cancer
• General Description: Canertinib (CI-1033) is a 4-anilinoquinazoline derivative originally developed as a human EGFR inhibitor, which has demonstrated low micromolar efficacy against *Trypanosoma brucei* in the context of repurposing kinase scaffolds for neglected disease drug discovery. Its structural features, including a morpholinopropyloxy and vinylcarbonylamino substituent, contribute to its activity, though further optimization is needed to enhance pharmacokinetic properties for treating human African trypanosomiasis (HAT).

Technology Process of Canertinib

There total 9 articles about Canertinib 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: 92.9%

N-[4-[(3-chloro-4-fluoro-phenyl)-(3,4-dimethoxy-benzyl)-amino]-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide → canertinib (267243-28-7)

Guidance literature:

With trifluoroacetic acid; for 6h; Heating / reflux;

Reference yield: 73.0%

→ canertinib (267243-28-7)

Guidance literature:

Reference yield: 38.0%

acrylic acid (79-10-7) + (3-CHLORO-4-FLUOROPHENYL)-[7-(3-MORPHOLIN-4-YL-PROPOXY)-6-AMINO-QUINAZOLINE-4-YL]-AMINE (267243-68-5) → canertinib (267243-28-7)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl acetamide;

DOI:10.1021/jm990482t

upstream raw materials:

acrylic acid

(3-CHLORO-4-FLUOROPHENYL)-[7-(3-MORPHOLIN-4-YL-PROPOXY)-6-AMINO-QUINAZOLINE-4-YL]-AMINE

3-morpholin-4-ylpropan-1-ol

3-chloro-4-fluorophenylamine

Refernces

Kinase scaffold repurposing for neglected disease drug discovery: Discovery of an efficacious, lapatanib-derived lead compound for trypanosomiasis

10.1021/jm400349k

This research presents the repurposing of kinase scaffolds for the discovery of new drugs to combat neglected tropical diseases, specifically focusing on human African trypanosomiasis (HAT), a disease caused by the protozoan parasite Trypanosoma brucei. The study aims to expedite drug discovery by utilizing chemical scaffolds from drugs approved for other indications, demonstrating the potential of lapatinib and canertinib, two 4-anilinoquinazolines with low micromolar EC50 values against T. brucei. The researchers synthesized and tested several potent 4-anilinoquinazolines, leading to the identification of NEU617 (23a), a highly potent and orally bioavailable inhibitor of trypanosome replication. The compound 23a was found to block kinetoplast duplication and arrest cytokinesis in trypanosomes, offering a new chemical tool for studying the regulation of the trypanosome cell cycle. The study concludes that compounds based on established human EGFR inhibitor chemotypes can be effective against HAT and that further optimization of these chemotypes is necessary to improve their pharmacokinetic properties and effectiveness in treating HAT. The chemicals used in the process include a series of 4-anilinoquinazoline derivatives, with lapatinib (GW572016, 1) and canertinib (CI-1033) as the starting points for optimization.