Combretastatin A4

Base Information

• Chemical Name: Combretastatin A4
• CAS No.: 117048-59-6
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.354
• Hs Code.: 29095000
• European Community (EC) Number: 631-427-6
• NSC Number: 613729
• UNII: 16U6OP69RQ
• DSSTox Substance ID: DTXSID101025983
• Nikkaji Number: J424.288B
• Wikipedia: Combretastatin_A-4
• Wikidata: Q5150955
• NCI Thesaurus Code: C2711
• Pharos Ligand ID: H9SSQYFZL1HD
• Metabolomics Workbench ID: 143437
• ChEMBL ID: CHEMBL67
• Mol file: 117048-59-6.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 Combretastatin A4

Chemical Property:

• Appearance/Colour: crystalline powder
• Vapor Pressure: 3.09E-10mmHg at 25°C
• Melting Point: 84.5-85.5 °C
• Refractive Index: 1.607
• Boiling Point: 490.269 °C at 760 mmHg
• PKA: 9.65±0.10(Predicted)
• Flash Point: 250.306 °C
• PSA: 57.15000
• Density: 1.184 g/cm³
• LogP: 3.59700
• Storage Temp.: Desiccate at -20°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 316.13107373
• Heavy Atom Count: 23
• Complexity: 358

Purity/Quality:

99% ^*data from raw suppliers

Combretastatin A4 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-41
• Safety Statements: 26-36/37-39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)O
• General Description: Combretastatin A-4 (CA-4) is a potent tubulin polymerization inhibitor originally isolated from the African tree *Combretum caffrum*. It exhibits significant anti-cancer activity by disrupting microtubule dynamics, leading to vascular disruption in tumors. CA-4 and its synthetic analogues, such as DMU-212, have been explored for their chemotherapeutic potential, with some derivatives demonstrating dual-targeting capabilities against both tubulin and DNA, enhancing their antitumor efficacy. These compounds have shown promise in preclinical studies, including inhibition of tumor growth in vivo, making them candidates for further development as novel cancer therapies.

Technology Process of Combretastatin A4

There total 135 articles about Combretastatin A4 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: 96.35%

C37H34O5 → combrestatin A4 (117048-62-1,117048-59-6)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 3h;

Reference yield: 95.0%

2-(3-hydroxy-4-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)ethyne (185698-55-9) → combrestatin A4 (117048-62-1,117048-59-6)

Guidance literature:

With ethanol; (NCP)IrHCl; tert-butylamine; at 75 ℃; for 24h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c01472

Reference yield: 92.0%

(Z)-5-(3-((2-methoxyethoxy)methoxy)-4-methoxystyryl)-1,2,3-trimethoxybenzene (1362101-30-1) → combrestatin A4 (117048-62-1,117048-59-6)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1021/ol300276p

upstream raw materials:

(Z)-5-(3-tert-butyldimethylsilyloxy-4-methoxystyryl)-1,2,3-trimethoxybenzene

{2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenoxy}-dimethyl-(1,1,2-trimethyl-propyl)-silane

2-(3-hydroxy-4-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)ethyne

(Z)-5-(2'-bromoethenyl)-2-methoxyphenol

Downstream raw materials:

methyl (combretastatinyl 2,3,4-tri-O-isobutyryl-β-D-glucopyranosid)uronate

combretastatinyl 2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranoside

combretastatin melibioside heptaisobutyryl ester

erianin

Refernces

A Ramberg-Baecklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212

10.1039/b702411h

The study presents a concise synthetic route to the anti-cancer agents combretastatin A-4 and DMU-212 using the Ramberg–B?cklund reaction. Combretastatin A-4, isolated from the African tree Combretum caffrum, is a potent inhibitor of tubulin polymerization, while DMU-212 is a synthetic analogue with cancer chemoprotective activity. The synthesis of combretastatin A-4 begins with the coupling of thiol 13, prepared from 3,4,5-trimethoxybenzyl alcohol using Lawesson’s reagent, and bromide 14, using potassium hydroxide in ethanol. The resulting sulfide is oxidized with m-chloroperoxybenzoic acid to form sulfone 12. The Ramberg–B?cklund reaction, carried out under various conditions (Meyers, Chan, and Franck), converts sulfone 12 into the stilbene intermediate 15, which is then desilylated to yield combretastatin A-4. The study also explores the synthesis of other combretastatin analogues, including (E)- and (Z)-2012, using similar procedures. The Ramberg–B?cklund reaction is further applied to prepare DMU-212 from sulfone 29, derived from 4-methoxybenzyl mercaptan and bromide 17. The study highlights the efficiency and stereoselectivity of the Ramberg–B?cklund reaction in synthesizing these anti-cancer stilbenes and provides insights into the reaction's scope and limitations.

Novel diaryl-2H-azirines: Antitumor hybrids for dual-targeting tubulin and DNA

10.1016/j.ejmech.2021.113256

The study presents the design and synthesis of a novel class of diaryl-substituted 2H-azirines, which are hybrid antitumor agents targeting both tubulin and DNA. These compounds were developed by combining pharmacophores from Combretastatin A-4 (CA-4), a known tubulin polymerization inhibitor, and aziridine-type alkylating agents, which are DNA damaging agents. The primary aim was to evaluate the antitumor activities of these compounds in vitro against various cancer cell lines and to investigate their mechanism of action. The most potent compound, 6h, showed significant activity against four cancer cell lines with low IC50 values and demonstrated dual-targeting capabilities in mechanistic studies. It inhibited tubulin polymerization, induced DNA damage, triggered cellular apoptosis, and showed anti-angiogenic effects. The study also included in vivo testing in a nude mice xenograft model, where 6h significantly inhibited tumor growth with low toxicity, indicating its potential for further development as a novel cancer therapy with a unique mechanism of action.

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