Total synthesis and neuritotrophic activity of farinosone C and derivatives.
An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling L-tyrosinol-amide as the pharmacophore.
Jessen
Henning J
HJ
Swiss Federal Institute of Technology (EPFL), Chemical Synthesis Laboratory (SB-ISIC-LSYNC), 1015 Lausanne, Switzerland.
Barbaras
Damien
D
Hamburger
Matthias
M
Gademann
Karl
K
D000818:Animals; D020932:Nerve Growth Factor / Q000494:pharmacology; D016501:Neurites / Q000187:drug effects* / Q000378:metabolism; D016716:PC12 Cells; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D010636:Phenols; C495162:farinosone C; D020932:Nerve Growth Factor