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
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL67
ChemSpider	4508364
ECHA InfoCard	100.159.667
PubChem	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- Key: HVXBOLULGPECHP-WAYWQWQTSA-N
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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.^[2][3]

Function

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 isomers, only one of which inhibits polymerization.^[3][4]

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. A large number of synthetic derivatives have been reported, including beta-lactam based compounds.^[5]

See also

• Ombrabulin, a combretastatin A-4 derivative in clinical trials for treatment of cancer

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
2. Determination of Combretastatin A-4 in Combretum leprosum. SCN Queiroz, MR Assalin, S Nobre, IS Melo, RM Moraes, VL Ferracini and AL Cerdeira, Planta Med, 2010, volume 76, pages 53, doi:10.1055/s-0030-1251815
3. Gill, Rupinder; Kaur, Ramandeep; Kaur, Gurneet; Rawal, Ravindra; Shah, Anamik; Bariwal, Jitender. "A Comprehensive Review on Combretastatin Analogues as Tubulin Binding Agents". Current Organic Chemistry. 18 (19): 2462–2512. doi:10.2174/138527281819141028114428.
4. "Colourful chemotherapy". The Economist. July 11, 2015. ISSN 0013-0613. Retrieved 2016-06-19.
5. O'Boyle, N; Miriam Carr; Lisa M. Greene; Orla Bergin; Seema M. Nathwani; Thomas McCabe; David G. Lloyd; Daniela M Zisterer; Mary J. Meegan (2010). "Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents.". Journal of Medicinal Chemistry. 53 (24): 8569–8584. doi:10.1021/jm101115u. PMID 21080725.