Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge.
Concise synthesis of BC-ring model compounds of 13E,17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity.
Kotoku
Naoyuki
N
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. kobayasi@phs.osaka-u.ac.jp
Tamada
Nao
N
Hayashi
Asami
A
Kobayashi
Motomasa
M
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D042783:Endothelial Cells / Q000187:drug effects; D006801:Humans; D007214:Indonesia; D007624:KB Cells; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D020533:Angiogenesis Inhibitors; D014315:Triterpenes; C530870:globostellatic acid X methyl ester