Combretastatin A-1

Combretastatin A-1
Names

IUPAC name 3-Methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol
Other names Combretastatin A1; OXi4500
Identifiers
CAS Number	109971-63-3^N
ChEMBL	ChEMBL520204^Y
ChemSpider	4800178^Y
Jmol interactive 3D	Image
PubChem	6078282
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	332.35 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 caffrum, the Eastern Cape South African Bushwillow tree.^[1]

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

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 2 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.
↑ http://clinicaltrials.gov/ct2/show/NCT01085656

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)

Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

oligostilbenoids

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