Azaspirene

Structure
NPEdia
Producing organism
Neosartorya sp.
Biological activity
antiangiogenic activity
Abstract
Azaspirene isolated from the fungus Neosartorya sp. is a novel angiogenesis inhibitor with a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton. Azaspirene inhibits the endothelial migration induced by vascular endothelial growth factor (ED100 = 27.1 µM).
References
isolation and structural determination
  • Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H.: Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp.
    Org Lett, 4(17): 2845-2848 (2002) PMID: 12182570
  • synthesis by other group
  • Hayashi Y, Shoji M, Yamaguchi J, Sato K, Yamaguchi S, Mukaiyama T, Sakai K, Asami Y, Kakeya H, Osada H.: Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor.
    J Am Chem Soc, 124(41): 12078-12079 (2002) PMID: 12371831