Combretastatin A-4

Combretastatin A-4
Names
Preferred IUPAC name
2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenol
Other names
Combretastatin A4
CA-4
1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl)ethene
3,4,5-Trimethoxy-3′-hydroxy-4′-methoxystilbene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.159.667 Edit this at Wikidata
UNII
  • 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- checkY
    Key: HVXBOLULGPECHP-WAYWQWQTSA-N checkY
  • COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
Properties
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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Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum afrum, the Eastern Cape South African bushwillow tree or in Combretum leprosum, the mofumbo, a species found in Brazil.[2][3]

  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 (10): 1666–1672, doi:10.1021/jm00010a011, PMID 7752190
  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 (2014). "A Comprehensive Review on Combretastatin Analogues as Tubulin Binding Agents". Current Organic Chemistry. 18 (19): 2462–2512. doi:10.2174/138527281819141028114428.