Uvaricin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
(+)-Uvaricin
Uvaricin.svg
Names
IUPAC name
3-(13-(5′-(1-(acetyloxy)undecyl)octahydro(2,2′-bifuran) -5-yl)-13-hydroxytridecyl)-5-methyl-2(5H)-Furanone
Identifiers
3D model (Jmol)
ChemSpider
KEGG
Properties
C39H68O7
Molar mass 648.97 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 YesYN ?)
Infobox references

Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata.[1] Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion.[2] A method to synthesize uvaricin was first published in 1998,[3] and an improved stereoselective synthesis published in 2001.[4]

References[edit]

  1. ^ Jolad, S. D.; Hoffmann, J. J.; Schram, K. H.; Cole, J. R.; Tempesta, M. S.; Kriek, G. R.; Bates, R. B. (1982). "Uvaricin, a New Antitumor Agent from Uvaria accuminata (Annonaceae)". Journal of Organic Chemistry. 47 (16): 3151–3153. doi:10.1021/jo00137a024. 
  2. ^ Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. (1996). "Acetogenins from Annonaceae, Inhibitors of Mitochondrial Complex I". Phytochemistry. 42 (2): 253–271. doi:10.1016/0031-9422(95)00836-5. PMID 8688168. 
  3. ^ Yazbak, A.; Sinha, S. C.; Keinan, E. (1998). "Total Synthesis of Uvaricin" (PDF). Journal of Organic Chemistry. 63 (17): 5863–5868. doi:10.1021/jo980453a. PMID 11672188. 
  4. ^ Burke, S. D.; Jiang, L. (2001). "Formal Synthesis of Uvaricin via Palladium-Mediated Double Cyclization". Organic Letters. 3 (12): 1953–1956. doi:10.1021/ol0160304. PMID 11405753.