Cediranib

Base Information

• Chemical Name: Cediranib
• CAS No.: 288383-20-0
• Deprecated CAS: 790713-41-6,557795-03-6
• Molecular Formula: C₂₅H₂₇FN₄O₃
• Molecular Weight: 450.513
• Hs Code.: 2933599590
• European Community (EC) Number: 670-946-2
• UNII: NQU9IPY4K9
• DSSTox Substance ID: DTXSID10183035
• Nikkaji Number: J2.560.640J
• Wikipedia: Cediranib
• Wikidata: Q5057052
• NCI Thesaurus Code: C80867
• Pharos Ligand ID: GDLFMB2Z3T7L
• Metabolomics Workbench ID: 149279
• ChEMBL ID: CHEMBL491473
• Mol file: 288383-20-0.mol

Synonyms:4-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline;4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2Z)-but-2-enedioate;4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2Z)-but-2-enedioate (1:1);AZD 2171;AZD-2171;AZD-2171 maleate;AZD2171;AZD2171 maleate;cediranib;cediranib maleate;Recentin

Chemical Property of Cediranib

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.642
• Boiling Point: 626.557 °C at 760 mmHg
• PKA: 16.14±0.30(Predicted)
• Flash Point: 332.73 °C
• PSA: 72.50000
• Density: 1.286 g/cm³
• LogP: 5.16210
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 450.20671890
• Heavy Atom Count: 33
• Complexity: 625

Purity/Quality:

Cediranib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(N1)C=CC(=C2F)OC3=NC=NC4=CC(=C(C=C43)OC)OCCCN5CCCC5
• Recent ClinicalTrials: Phase II Umbrella Study of Novel Anti-cancer Agents in Patients With NSCLC Who Progressed on an Anti-PD-1/PD-L1 Containing Therapy
• Recent EU Clinical Trials: Phase II, Open-Label Study of preliminary efficacy of Durvalumab (MEDI4736) in Combination with Cediranib in Patients with Metastatic Uveal Melanoma
• Recent NIPH Clinical Trials: A Randomized Phase II/III study of the combination of Cediranib and Olaparib compared to Cediranib or Olaparib alone, or Standard of care chemotherapy in women with recurrent platinum-resistant or -refractory ovarian, fallopian tube, or primary peritoneal cancer (COCOS)
• Description: Receptors for VEGF have central roles in vasculogenesis and angiogenesis and thus serve as targets for cancer therapy. Cediranib is a potent inhibitor of VEGF receptor tyrosine kinases, including VEGFR1, 2, and 3 (IC50s = 5, 1, and 3 nM, respectively). It also potently inhibits a variety of other receptor and non-receptor tyrosine kinases, including several in the platelet-derived growth factor, fibroblast growth factor, and endothelial growth factor receptor families. Cediranib blocks tubule formation by human umbilical vein endothelial cells in vitro and prevents angiogenesis as well as xenograft tumor growth in vivo. Because of these effects, cediranib has potential use in a range of cancers.
• Uses: Cediranib (AZD2171) inhibited VEGF-stimulated proliferation and KDR phosphorylation with IC50 of 0.4 and 0.5 nM, respectively. Cediranib is a drug for blocking angiogenesis, study on cervical cancer molecular targeted drug and clinical application progress, value of correlative biomakers in the understanding of tumor biology.

Technology Process of Cediranib

There total 20 articles about Cediranib 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: 86.0%

1-(3-chloropropyl)pyrrolidine (39743-20-9) + 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-ol → cediranib (288383-20-0,557795-03-6)

Guidance literature:

With potassium carbonate; In 1-methyl-pyrrolidin-2-one; tert-butyl methyl ether; at 72 ℃; for 21.5h; Concentration; Kinetics; Inert atmosphere;

DOI:10.1021/acs.joc.8b02458

Reference yield: 80.0%

4-fluoro-2-methyl-1H-indol-5-ol (288385-88-6) + 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (199327-69-0) → cediranib (288383-20-0,557795-03-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 70 - 75 ℃; for 5.5h; Inert atmosphere;

Reference yield: 78.0%

7-hydroxy-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinazoline (574745-76-9) + 4-azoniaspiro[3,4]octane bromide (1022112-44-2) → cediranib (288383-20-0,557795-03-6)

Guidance literature:

With potassium carbonate; In 1-methyl-2-pyrrolidine; tert-butyl methyl ether; at 80 ℃; for 3.5h; Product distribution / selectivity;

upstream raw materials:

1-(3-chloropropyl)pyrrolidine

7-hydroxy-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinazoline

4-azaspiro[3.4]octan-4-ium chloride

4-azoniaspiro[3,4]octane bromide

Downstream raw materials:

cediranib maleate

Refernces

• 1、 -. "Preparation method of vascular endothelial growth factor (VEGF) receptor tyrosine kinase inhibitor Cediranib". Paragraph 0013-0015. . Retrieved 2018/06/15.
• 2、 -. "Preparation method for anti-cancer drug of Cediranib". Paragraph 0017; 0018; 0019. . Retrieved 2018/08/04.