Ombrabulin

Base Information

• Chemical Name: Ombrabulin
• CAS No.: 181816-48-8
• Molecular Formula: C₂₁H₂₆N₂O₆
• Molecular Weight: 402.447
• Hs Code.: 2924299090
• UNII: 82JB1524Q6
• DSSTox Substance ID: DTXSID50939477
• Nikkaji Number: J1.255.679I
• Wikipedia: Ombrabulin
• Wikidata: Q7089934
• NCI Thesaurus Code: C78480
• Metabolomics Workbench ID: 153780
• ChEMBL ID: CHEMBL572284
• Mol file: 181816-48-8.mol

Synonyms:AC 7700;AC-7700;AVE8062;N-(2-methxoy-5-(2-(3,4,5-trimethoxyphenyl)vinyl)pheyl)-serinamide hydrochloride;ombrabulin

Chemical Property of Ombrabulin

Chemical Property:

• Boiling Point: 648.1 °C at 760 mmHg
• PKA: 12.03±0.10(Predicted)
• Flash Point: 345.8 °C
• PSA: 112.27000
• Density: 1.258 g/cm³
• LogP: 2.92280
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 402.17908655
• Heavy Atom Count: 29
• Complexity: 517

Purity/Quality:

99% ^*data from raw suppliers

Ombrabulin ^*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)NC(=O)C(CO)N
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)NC(=O)[C@H](CO)N
• Recent ClinicalTrials: A Study of AVE8062 in Advanced-stage Soft Tissue Sarcoma After Failure of Anthracycline and Ifosfamide Chemotherapies
• Recent EU Clinical Trials: A Phase 2, Multi-Center, Double-Blind, placebo controlled, Randomized Study of
• Uses: Ombrabulin is a vascular disrupting agent that enhances the standard therapies in head and neck squamous cell carcinomas.

Technology Process of Ombrabulin

There total 12 articles about Ombrabulin 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: 61.0%

(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate (286463-65-8) → (S,Z)-2-amino-3-hydroxy-N-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)propanamide (181816-48-8)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/j.bmcl.2009.10.064

Reference yield:

Bz-Arg-Arg-Ser-combretamin → (S,Z)-2-amino-3-hydroxy-N-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)propanamide (181816-48-8) + Bz-Arg-Arg-H (113042-55-0)

Guidance literature:

With dengue virus protease; water; In dimethyl sulfoxide; at 37 ℃; for 2h; pH=9; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/acsmedchemlett.9b00058

Reference yield:

Bz-Lys-Arg-Ser-combretamin → (S,Z)-2-amino-3-hydroxy-N-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)propanamide (181816-48-8) + Bz-Lys-Arg-H

Guidance literature:

With dengue virus protease; water; In dimethyl sulfoxide; at 37 ℃; for 2h; pH=9; Enzymatic reaction;

DOI:10.1021/acsmedchemlett.9b00058

upstream raw materials:

(S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate

4-methoxy-3-nitrotoluene

3-nitro-4-methoxybenzyl bromide

3-amino-deoxycombretastatin A₄

Refernces

• 1、 Richter, Michael,Leuthold, Mila M.,Graf, Dominik,Bartenschlager, Ralf,Klein, Christian D.. "Prodrug Activation by a Viral Protease: Evaluating Combretastatin Peptide Hybrids to Selectively Target Infected Cells". supporting information. p. 1115 - 1121. Retrieved 2019/08/20.
• 2、 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.