Fosbretabulin

Base Information

• Chemical Name: Fosbretabulin
• CAS No.: 222030-63-9
• Molecular Formula: C18H21 O8 P
• Molecular Weight: 396.334
• UNII: I5590ES2QZ
• DSSTox Substance ID: DTXSID401028843
• Nikkaji Number: J2.217.024D
• Wikipedia: Combretastatin_A-4_phosphate,Fosbretabulin
• Wikidata: Q5150956
• NCI Thesaurus Code: C82378
• Metabolomics Workbench ID: 153543
• ChEMBL ID: CHEMBL1206232
• Mol file: 222030-63-9.mol

Synonyms:1-(3,4,5-trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)ethene;2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)vinyl)phenyl dihydrogen phosphate;3,4,5-trimethoxy-3'-hydroxy-4'-methoxystilbene;CA4DP;combretastatin A-4;combretastatin A-4 disodium phosphate;combretastatin A4;combretastatin A4 phosphate;CRC 87-09;CRC-98-09;deoxycombretastatin A-4;fosbretabulin;isocombretastatin A-4;NSC 817373;NSC-817373;phenol, 2-methoxy-5-((1z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-,1-(dihydrogen phosphate);phenol, 2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, dihydrogen phosphate

Chemical Property of Fosbretabulin

Chemical Property:

• Vapor Pressure: 7.99E-16mmHg at 25°C
• Refractive Index: 1.609
• Boiling Point: 611.8°Cat760mmHg
• PKA: 1.17±0.50(Predicted)
• Flash Point: 323.8°C
• PSA: 119.15000
• Density: 1.342g/cm³
• LogP: 4.23930
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 396.09740462
• Heavy Atom Count: 27
• Complexity: 508

Purity/Quality:

98%Min ^*data from raw suppliers

(Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)phenyldihydrogenphosphate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)OP(=O)(O)O
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)OP(=O)(O)O
• Recent ClinicalTrials: PAZOFOS: Phase Ib and Phase II Trial of Pazopanib +/- Fosbretabulin in Advanced Recurrent Ovarian Cancer
• Recent EU Clinical Trials: FOCUS: A Multicenter, Multinational, Double-blind, 2-Arm, Randomized, Phase 2/3, Study of Physician’s Choice Chemotherapy (PCC) (Weekly Paclitaxel or Pegylated Liposomal Doxorubicin [PLD]) Plus Bevacizumab and CA4P Versus PCC Plus Bevacizumab and Placebo for Subjects with Platinum-Resistant, Recurrent, Epithelial Ovarian, Primary Peritoneal or Fallopian Tube Cancer

Technology Process of Fosbretabulin

There total 9 articles about Fosbretabulin 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: 90.0%

3'-O-bis(benzyl)phosphoryl-combretastatin A-4 → combretastatin A-4 phosphate (222030-63-9)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; for 0.333333h; Product distribution / selectivity;

Reference yield: 70.0%

C24H37O8PSi2 → combretastatin A-4 phosphate (222030-63-9)

Guidance literature:

With sodium methylate;

DOI:10.1016/j.bmcl.2009.10.064

Reference yield:

C18H19Cl2O6P → combretastatin A-4 phosphate (222030-63-9)

Guidance literature:

With sodium hydroxide; In acetonitrile;

DOI:10.1080/00304940609356450

upstream raw materials:

3'-O-bis(tert-butyl)phosphorylcombretastatin

3'-O-bis(trimethylsilylethoxy)phosphorylcombretastatin

combrestatin A₄

Downstream raw materials:

combretastatin A-4 P tris(hydroxymethyl)aminomethane salt

Refernces

• 1、 Fuerst, Rita,Zupko, Istvan,Berenyi, Agnes,Ecker, Gerhard F.,Rinner, Uwe. "Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs". scheme or table. p. 6948 - 6951. Retrieved 2010/08/06.
• 2、 -. "Synthesis of combretastatin A-4 prodrugs and trans-isomers thereof". Page/Page column 11; 15-17. . Retrieved 2008/06/13.