Combretastatin A-4

Combretastatin A-4
IUPAC name

2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol
Other names

Combretastatin A4
CA-4
Identifiers
CAS number 117048-59-6 N
PubChem 5351344
ChemSpider 4508364 Y
ChEMBL CHEMBL67 Y
Jmol-3D images Image 1
Properties
Molecular formula C18H20O5
Molar mass 316.34 g/mol
Exact mass 316.131074 u
Melting point

116 °C[1]
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Combretastatin A-4 is a combretastatin, a type of stilbenoid. It can be isolated from Combretum caffrum, the Eastern Cape South African Bushwillow tree.

Derivatives

Combretastatin A-4 is the active component of combretastatin A-4 phosphate, a prodrug designed to damage the vasculature (blood vessels) of cancer tumors causing central necrosis.

See also

References

  1. ^ Pettit, G. R. Sheo Bux Singh Boyd, M. R. Hamel, E. (1995), "Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6", Journal of Medicinal Chemistry 38: 1666–1672, doi:10.1021/jm00010a011 
Stilbenoids and their glycosides
Stilbenoids
Combretastatin | Combretastatin A-1 | Combretastatin A-4 | Combretastatin B-1 | Piceatannol | Pinosylvin | Pterostilbene | Resveratrol
Glycosides
of resveratrol
Oligomeric forms
Ampelopsin A | Amurensin A, B, G and H | Carasinol B | Diptoindonesin C | Diptoindonesin F | Flexuosol A | Gnetin H | Hemsleyanol D | Kobophenol A | Laetevirenol A, B, C, D and E | Vaticanol B | Viniferal | Tetramers : Laetevirenol F and G
of resveratrol
Ampelopsin E | Dimers : ε-viniferin, Parthenocissin A, Quadrangularin A, Pallidol and Amurensin A | Trimers : α-viniferin, Laevifonol (an ε-viniferin-ascorbic acid hybrid compound), Malaysianol A, trans-diptoindonesin B | Tetramers : Hopeaphenol | Vitisins A, B and C
Oligomeric forms glycosides
Diptoindonesin A | Laevifoside (O-glucoside of ampelopsin A)
Misc
Synthetic
Stilbenoid drugs