Combretastatin A-4

Combretastatin A-4

Names
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
3D model (JSmol)	Interactive image
ChemSpider	4508364 Y
ECHA InfoCard	100.159.667
PubChem CID	5351344
InChI InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5- Y Key: HVXBOLULGPECHP-WAYWQWQTSA-N Y
SMILES COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
Properties
Chemical formula	C18H20O5
Molar mass	316.34 g/mol
Melting point	116 °C (241 °F; 389 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum caffrum, the Eastern Cape South African bushwillow tree or in Combretum leprosum, the mofumbo, a species found in Brazil.

Tubulin represents a potent target in cancer chemotherapy, given its role in cell division. Combretastatin is a naturally occurring well known tubulin polymerization inhibitor. Combretastatin A-4 comes in two stereoisomers (cis (shown top right), and trans); The cis form binds much better to the 'colchicine' site on tubulin to inhibit polymerization.

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.

A large number of synthetic derivatives have been reported, including beta-lactam based compounds.