Liphagal, a Selective inhibitor of PI3 kinase alpha isolated from the sponge akacoralliphaga: structure elucidation and biomimetic synthesis.
[structure: see text] Liphagal (1), a selective inhibitor of PI3K alpha, has been isolated from the marine sponge Aka coralliphaga collected in Dominica. The "liphagane" meroterpenoid carbon skeleton of liphagal (1) is new. A biomimetic total synthesis has been used to confirm the constitution of liphagal (1) and support a proposed biogenesis.
Marion
Frederic
F
Department of Chemistry, University of British Columbia, Vancouver, Canada.
Williams
David E
DE
Patrick
Brian O
BO
Hollander
Irwin
I
Mallon
Robert
R
Kim
Steven C
SC
Roll
Deborah M
DM
Feldberg
Larry
L
Van Soest
Rob
R
Andersen
Raymond J
RJ
D000730:Androstadienes / Q000494:pharmacology; D000818:Animals; D002867:Chromones / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009025:Morpholines / Q000494:pharmacology; D000081082:Phosphoinositide-3 Kinase Inhibitors; D011161:Porifera / Q000737:chemistry*; D013729:Terpenes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D014407:Tumor Cells, Cultured; D000077191:Wortmannin
D000730:Androstadienes; D002867:Chromones; D009025:Morpholines; D000081082:Phosphoinositide-3 Kinase Inhibitors; D013729:Terpenes; C513880:liphagal; C085911:2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one; D000077191:Wortmannin