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 δ20(22)-pseudo compound, which was then subjected to ozonolysis to provide a pregnane derivative in a total 54% yield showing neuritogenic and NGF-enhancing...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2007, Vol.55(7), pp.1077-1078
Hauptverfasser:	Matsushita, Sayaka, Yanai, Yoshihiro, Fusyuku, Asami, Fujiwara, Yukio, Ikeda, Tsuyoshi, Ono, Masateru, Han, Chunguang, Ojika, Makoto, Nohara, Toshihiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetic Acid - chemistry Acetylation Animals Cell Line Lycopersicon esculentum - chemistry Molecular Structure Nerve Growth Factors - chemical synthesis Nerve Growth Factors - chemistry Nerve Growth Factors - pharmacology Neurites - drug effects neuritogenic activity ozonolysis PC12 Cells Plant Components, Aerial - chemistry pregnane derivative Pregnanes - chemical synthesis Pregnanes - chemistry Pregnanes - pharmacology Pyridines - chemistry Rats tomatidine Tomatine - analogs & derivatives Tomatine - chemistry δ20-pseudo compound
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Beschreibung
Zusammenfassung:	Moderate acetylation of tomatidine with anhydrous acetic acid and pyridine for 20 h at r.t., followed by pseudomerization in ice-water, gave a δ20(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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.55.1077