Efficient conversion of tomatidine into neuritogenic pregnane derivative.
Moderate acetylation of tomatidine with anhydrous acetic acid and pyridine for 20 h at r.t., followed by pseudomerization in ice-water, gave a delta(20(22))-pseudo compound, which was then subjected to ozonolysis to provide a pregnane derivative in a total 54% yield showing neuritogenic and NGF-enhancing activities.
Matsushita
Sayaka
S
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.
Yanai
Yoshihiro
Y
Fusyuku
Asami
A
Fujiwara
Yukio
Y
Ikeda
Tsuyoshi
T
Ono
Masateru
M
Han
Chunguang
C
Ojika
Makoto
M
Nohara
Toshihiro
T
D019342:Acetic Acid / Q000737:chemistry; D000107:Acetylation; D000818:Animals; D002460:Cell Line; D018551:Solanum lycopersicum / Q000737:chemistry*; D015394:Molecular Structure; D009414:Nerve Growth Factors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016501:Neurites / Q000187:drug effects*; D016716:PC12 Cells; D035261:Plant Components, Aerial / Q000737:chemistry; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D011725:Pyridines / Q000737:chemistry; D051381:Rats; D014053:Tomatine / Q000031:analogs & derivatives* / Q000737:chemistry
D009414:Nerve Growth Factors; D011278:Pregnanes; D011725:Pyridines; C003677:tomatidine; D014053:Tomatine; C023666:pyridine; D019342:Acetic Acid