Avarone

Chemical Name: 2-[(1R)-1,2,3,4,4a,7,8,8a,alpha-Octahydro-1beta,2beta,4abeta,5-tetramethyl-1-naphthylmethyl]quinone
项目整合开发状态: Biological Testing
项目研究机构: Johannes Gutenberg-Universit鋞 Mainz (Originator)
合成路线:Avarol (I) has been isolated from the marine sponge Dysidea avara,which is ubiquitous near the Atlantic coast of Europe.in the Mediterranean and around the Maldive Islands.The ground material is extracted with ethyl acetate.The organic phase is dried over Mg2SO4 and then evaporated to dryness yielding a tar-like residue.This material is taken up in benzene and purified by silica gel column chromatography using benzene/10% ethyl acetate as solvent.The avarol fractions are concentrated; purified avaro is obtained after several crystallizations from acetone-methylene chloride,with yield of 2.7 g avarol from 1kg of fresh material.Avarone is obtained from its corresponding hydroquinone avarol (I) by Ag2O oxidation.
📌 参考资料/链接:
参考文献标题:Avarone and Avarol
文献作者:M黮ler,W.E.G.; Zahn,R.K.; Maidhof,A.; Gasic,M.J.; Schr鰀er,H.C.; Eich,E.
参考来源:Drugs Fut 1985,10(11),887

📄 详细内容


合成路线:Avarol (I) has been isolated from the marine sponge Dysidea avara,which is ubiquitous near the Atlantic coast of Europe.in the Mediterranean and around the Maldive Islands.The ground material is extracted with ethyl acetate.The organic phase is dried over Mg2SO4 and then evaporated to dryness yielding a tar-like residue.This material is taken up in benzene and purified by silica gel column chromatography using benzene/10% ethyl acetate as solvent.The avarol fractions are concentrated; purified avaro is obtained after several crystallizations from acetone-methylene chloride,with yield of 2.7 g avarol from 1kg of fresh material.Avarone is obtained from its corresponding hydroquinone avarol (I) by Ag2O oxidation.

参考文献标题:Avarol,a cytostatically active compound from the marine sponge Dysidea avara
文献作者:Zahn,R.K.; Dogovic,N.; Eich,E.; Gasic,M.J.; Diehl-Seifert,B.; Maidhof,A.; Becker,C.; M黮ler,W.E.G.
参考来源:Comp Biochem Physiol (C) 1985,80(1),47-52


合成路线:Avarol (I) has been isolated from the marine sponge Dysidea avara,which is ubiquitous near the Atlantic coast of Europe.in the Mediterranean and around the Maldive Islands.The ground material is extracted with ethyl acetate.The organic phase is dried over Mg2SO4 and then evaporated to dryness yielding a tar-like residue.This material is taken up in benzene and purified by silica gel column chromatography using benzene/10% ethyl acetate as solvent.The avarol fractions are concentrated; purified avaro is obtained after several crystallizations from acetone-methylene chloride,with yield of 2.7 g avarol from 1kg of fresh material.Avarone is obtained from its corresponding hydroquinone avarol (I) by Ag2O oxidation.

参考文献标题:Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo
文献作者:Maidhof,A.; Schr鰀er,H.C.; Kurelec,B.; Seibert,G.; Gasic,M.J.; Eich,E.; Bernd,A.; Heidemann,D.; M黮ler,W.E.G.; Zahn,R.K.
参考来源:Cancer Res 1985,45(10),4822


合成路线:Avarol (I) has been isolated from the marine sponge Dysidea avara,which is ubiquitous near the Atlantic coast of Europe.in the Mediterranean and around the Maldive Islands.The ground material is extracted with ethyl acetate.The organic phase is dried over Mg2SO4 and then evaporated to dryness yielding a tar-like residue.This material is taken up in benzene and purified by silica gel column chromatography using benzene/10% ethyl acetate as solvent.The avarol fractions are concentrated; purified avaro is obtained after several crystallizations from acetone-methylene chloride,with yield of 2.7 g avarol from 1kg of fresh material.Avarone is obtained from its corresponding hydroquinone avarol (I) by Ag2O oxidation.
参考文献标题:Avarol,a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge Dysidea avara
文献作者:Minale,L.; Riccio,R.; Sodano,G.
参考来源:Tetrahedron Lett 1974,363401