Synthesis of optically active methyl 7 beta-hydroxykaurenoate with potent neuroprotective activity.
(-)-Methyl 7 beta-hydroxykaurenoate (3) and its 4-demethyl acetate (-)-4 were both synthesized via methods that contained radical cyclization and intramolecular Diels-Alder reactions as key steps. Both compounds displayed potent neuroprotective activity against N-methyl-D-aspartate toxicity in cultured cortical neurons.
Toyota
Masahiro
M
Department of Organic Chemistry, Tohoku University, Graduate School of Pharmaceutical Sciences, Aobayama, Sendai 980-8578, Japan.
Matsuura
Kiminori
K
Yokota
Masahiro
M
Kimura
Manami
M
Yonaga
Masahiro
M
Sugimoto
Hachiro
H
Ihara
Masataka
M
D000818:Animals; D002478:Cells, Cultured; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D016202:N-Methylaspartate / Q000037:antagonists & inhibitors; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000494:pharmacology
D004224:Diterpenes; D018696:Neuroprotective Agents; C496439:methyl 7 beta-hydroxykaurenoate; C496438:methyl 7 beta-hydroxykaurenoate 4-demethyl acetate; D016202:N-Methylaspartate