Combretastatin A-1

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Combretastatin A-1
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
PubChem 6078282
ChemSpider 4800178 YesY
ChEMBL CHEMBL520204 YesY
Jmol-3D images Image 1
Properties
Molecular formula C18H20O6
Molar mass 332.35 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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) is in Phase I clinical trials. [2]

References

  1. ↑ 1.0 1.1 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. ↑ http://clinicaltrials.gov/ct2/show/NCT01085656
Aglycones
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
  • 4-Methoxyresveratrol
  • Gnetucleistol D (2-methoxyoxyresveratrol)
  • Gnetucleistol E (3-methoxy-isorhapontigenin)
  • Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene)
  • Pterostilbene
  • Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene)
Combretastatins:
carboxylated
other acetylations
Glycosides
  • Astringin (Piceatannol 3-O-glucoside)
  • Foeniculoside I, II, III and IV
  • Isorhapontin (Isorhapontigenin glucoside)
  • Mulberroside A (Oxyresveratrol diglucoside)
of resveratrol
of rhapontigenin
  • Rhapontigenin 3-O-rutinoside
    • 4'-Methoxy-(E)-resveratrol 3-O-rutinoside
  • Rhaponticin (Rhapontigenin glucoside)
Oligomeric forms
  • Ampelopsin C, E and H
  • Amurensin A, B, G and H
  • Balanocarpol
  • Carasinol B
  • Dibalanocarpol
  • Diptoindonesin C
  • Diptoindonesin F
  • Flexuosol A
  • Gnetin H
  • Hemsleyanol D
  • Isohopeaphenol
  • Kobophenol A
  • Laetevirenol A, B, C, D and E
  • Malibatol A and B
  • Suffruticosol A and B
  • Vaticanol C
  • Viniferal
  • E-ω-viniferin
  • Z-ω-viniferin
Tetramers:
  • Laetevirenol F and G
of resveratrol
Dimers
Trimers
Tetramers
  • Amurensin E
  • F and K
  • Gnetuhainin R (isorhapontigenin tetramer)
  • Hopeaphenol
  • Vaticanol B
  • Vitisin A
  • B and C
  • β-viniferin (cyclic resveratrol tetramer)
Pentamers
  • Amurensin E and F
Higher polymers
  • γ-viniferin
Oligomeric forms
glycosides or conjugates
  • Diptoindonesin A
  • Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
  • Laevifoside (O-glucoside of ampelopsin A)
Synthetic
  • Stilbenoid drugs
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