(7aR,8aβ,11aβ,11bα,11cβ)-2β-[(2S,4S)-テトラヒドロ-4-メチル-5-オキソフラン-2-イル]-8β-エチルテトラデカヒドロ-11β-メチルフロ[2,3-h]ピロロ[3,2,1-jk][1]ベンゾアゼピン-10-オン 化学特性,用途語,生産方法
説明
This novel alkaloid has been isolated from Sternona sessilifolia and S. tuberosa
and was first given the formula C19H29O4N, subsequently altered to that given
above. It crystallizes in colourless needles from MeOH with 1 mole of solvent,
m.p. 65-88°C (dec.) and has [α]
D - 25.4° (Me2CO). It is a non-phenolic,
tertiary base and yields a hydrobromide, m.p. 120°C (dec.) and a perchlorate,
m.p. 242°C (dec.). The methiodide monohydrate has m.p. 236-8°C (dec.) and
the methochloride, dihydrate, m.p. 172°C. A methosulphate has also been
prepared, m.p. 253°C (dec.). The base is not hydrolyzed by acids but in the
presence of excess PtO2 it gives the dihydro derivative, m.p. 133°C, furnishing a
hydrochloride, m.p. 281 ° C. Oxidation with KMnO4 gives a C17 compound,
whereas oxidation with silver oxide forms a neutral substance, C22H29O4N, m.p.
178°C which still contains the lactone groups and gives a positive Ehrlich
pyrrole reaction.
使用
Tuberostemonine is elucidated as one of the major components of Radix Stemonae and has been shown to display therapeutic effects against cigarette smoke-induced acute lung inflammation.
定義
ChEBI: A natural product found in Stemona phyllantha and Stemona tuberosa.
参考文献
Kondo, Suzuki, Satomi.,J. Pharrn. Soc., Japan, 54,96 (1934)
Kondo, Suzuki, Satomi., ibid, 59, 177 (1939)
Kondo, Suzuki, Satomi., ibid, 60, 149 (1940)
Kondo, Suzuki, Satomi., ibid, 61, 111 (1941)
Kaneko., Ann. Rep. ITSUU Lab. (Tokyo), 11,45 (1960)
Gotz, Bogri, Gray., Tetrahedron Lett., 707 (1961)
Edwards, Feniak, Handa., Can. J. Chern., 40,455,2416 (1962)
Crystal structure:
Harada et ai., Chern. Cornrnun., 460 (1967)
(7aR,8aβ,11aβ,11bα,11cβ)-2β-[(2S,4S)-テトラヒドロ-4-メチル-5-オキソフラン-2-イル]-8β-エチルテトラデカヒドロ-11β-メチルフロ[2,3-h]ピロロ[3,2,1-jk][1]ベンゾアゼピン-10-オン 上流と下流の製品情報
原材料
Furo[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one, 8-ethenyldodecahydro-11-methyl-2-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-, (2S,7aR,8R,8aS,11S,11aS,11bR,11cR)-
1H-Indole-1,2-dicarboxylic acid, 2,3,3a,6,7,7a-hexahydro-6-hydroxy-, 2-methyl 1-(phenylmethyl) ester, [2S-(2α,3aβ,6β,7aα)]- (9CI)
準備製品
Furo[2,?3-?h]?pyrrolo[3,?2,?1-?jk]?[1]?benzazepin-?10(4H)?-?one, 8-?ethyl-?5,?6,?7,?7a,?8,?8a,?11,?11a-?octahydro-?11-?methyl-?2-?[(2S,?4S)?-?tetrahydro-?4-?methyl-?5-?oxo-?2-?furanyl]?-?, (7aR,?8R,?8aS,?11S,?11aR)?-