Combretastatin A-4

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Combretastatin A-4
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
PubChem 5351344
ChemSpider 4508364 YesY
ChEMBL CHEMBL67 YesY
Jmol-3D images Image 1
Properties
Molecular formula C18H20O5
Molar mass 316.34 g/mol
Melting point 116 °C[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-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]

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.[3]

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. ↑ O'Boyle, N; Miriam Carr, Lisa M. Greene, Orla Bergin, Seema M. Nathwani, Thomas McCabe, David G. Lloyd, Daniela M Zisterer, and Mary J. Meegan (2010). Journal of Medicinal Chemistry 53 (24): 8569–8584. doi:10.1021/jm101115u. 
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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