Combretastatin A-1

Combretastatin A-1

Names
Preferred IUPAC name 3-Methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]benzene-1,2-diol
Other names Combretastatin A1; OXi4500
Identifiers
CAS Number	109971-63-3^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL520204^Y
ChemSpider	4800178^Y
PubChem CID	6078282
UNII	2222ATS339^Y
InChI InChI=1S/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5+^Y Key: YUSYSJSHVJULID-AATRIKPKSA-N^Y
SMILES COC1=C(C(=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O)O
Properties
Chemical formula	C18H20O6
Molar mass	332.352 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Combretastatin A-1 is a combretastatin and a stilbenoid. It can be found in Combretum afrum, the Eastern Cape South African Bushwillow tree.[1]

Biological effects in mammals

It is an antiangiogenic agent acting by destabilizing tubulin, which induces cell apoptosis of proliferating endothelial cells.[1]

Derivatives as drugs

Currently designated an orphan drug by the FDA, combretastatin A1 diphosphate (OXi4503 or CA1P) is in Phase I clinical trials for relapsed and refractory acute myeloid leukemia and myelodysplastic syndrome.[2]

References

1. Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.; Schmidt, J. M. (1987). "Isolation, Structure, and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum". Journal of Natural Products. 50 (1): 119–131. doi:10.1021/np50049a016. PMID 3598594.
2. "A Phase I Clinical Trial of OXi4503 for Relapsed and Refractory Acute Myelogenous Leukemia (AML) and Myelodysplastic Syndromes (MDS)". 7 August 2017.