The synthesis and preliminary biological evaluation of a novel steroid with neurotrophic activity: NGA0187.
[structure, reaction: see text] A full account of the total synthesis of neurotrophic compound NGA0187 is provided. A key feature of the synthesis involved the direct selective oxidation of 6alpha,7beta-diol to install the unusual 6,7-ketol moiety and stereoselective conjugate addition of vinyl cuprate to enone. A preliminary evaluation of its ability to stimulate the neurite outgrowth was also evaluated with PC12 cell.
Hua
Zihao
Z
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
Carcache
David A
DA
Tian
Yuan
Y
Li
Yue-Ming
YM
Danishefsky
Samuel J
SJ
D000818:Animals; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004353:Drug Evaluation, Preclinical; D008958:Models, Molecular; D008968:Molecular Conformation; D020932:Nerve Growth Factor / Q000494:pharmacology; D009474:Neurons / Q000187:drug effects*; D016716:PC12 Cells; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C466781:NGA 0187; D014315:Triterpenes; D020932:Nerve Growth Factor