7-Oxoprostacyclin monosodium salt, 7-Oxosprostaglandin I2 monosodium, 7-Oxo-PGI2 sodium
Chemical Name: (5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxy-7-oxoprosta-5,13-dien-1-oic acid monosodium salt
CAS No. 79673-16-8
项目整合开发状态: Biological Testing
项目研究机构: Chinoin (Originator)
合成路线:The reaction of prostaglandin F2alpha (I) with tallium tri-acetate in acetic acid gives the inner ketal (II),which by trans-ketalization with BF3 and methanol is converted into the diol methyl ketal (III).Silylation of (III) with dimethyl-tert-butylsilyl chloride and imidazole in DMF yields the disilylated compound (IV),which is deacetylated with K2CO3 in methanol affording the alcohol (V).Collins' oxidation of (V) with CrO3-pyridine in methylene chloride gives the ketone (VI),which is deprotected with tetrabutylammonium fluoride in THF yielding the dihydroxy ketone (VII).Heating of (VII) at 160 C in HMPA affords 7-oxo-PGI2 methyl ester (VIII),which is finally hydrolyzed with NaOH in methanol-water.
📌 参考资料/链接：
参考文献标题:7-Oxo-PGI2-derivs.and process for the preparation thereof and pharmaceutical compsns.containing same
文献作者:Ivanics,J.; Kov醕s,G.; Papp,?; Pall醙i,I.; D閞,J.; Simonidesz,V.; Stadler,I.(Chinoin Pharmaceutical and Chemical Works Co.,Ltd.)
参考来源:US 4330553
📄 详细内容
合成路线:The reaction of prostaglandin F2alpha (I) with tallium tri-acetate in acetic acid gives the inner ketal (II),which by trans-ketalization with BF3 and methanol is converted into the diol methyl ketal (III).Silylation of (III) with dimethyl-tert-butylsilyl chloride and imidazole in DMF yields the disilylated compound (IV),which is deacetylated with K2CO3 in methanol affording the alcohol (V).Collins' oxidation of (V) with CrO3-pyridine in methylene chloride gives the ketone (VI),which is deprotected with tetrabutylammonium fluoride in THF yielding the dihydroxy ketone (VII).Heating of (VII) at 160 C in HMPA affords 7-oxo-PGI2 methyl ester (VIII),which is finally hydrolyzed with NaOH in methanol-water.
参考文献标题:7-Oxo-PGI2 Sodium
文献作者:Castar,J.; Serradell,M.N.; Hillier,K.; Blancafort,P.
参考来源:Drugs Fut 1983,8(7),598
合成路线:The reaction of prostaglandin F2alpha (I) with tallium tri-acetate in acetic acid gives the inner ketal (II),which by trans-ketalization with BF3 and methanol is converted into the diol methyl ketal (III).Silylation of (III) with dimethyl-tert-butylsilyl chloride and imidazole in DMF yields the disilylated compound (IV),which is deacetylated with K2CO3 in methanol affording the alcohol (V).Collins' oxidation of (V) with CrO3-pyridine in methylene chloride gives the ketone (VI),which is deprotected with tetrabutylammonium fluoride in THF yielding the dihydroxy ketone (VII).Heating of (VII) at 160 C in HMPA affords 7-oxo-PGI2 methyl ester (VIII),which is finally hydrolyzed with NaOH in methanol-water.
参考文献标题:A new stable prostacyclin mimic,7-oxo-PGI2
文献作者:Kov郼s,G.; Simonidesz,V.; Tomoskozi,I.; Kormoczy,P.; Szekely,I.; Papp-Behr,A.; Stadler,I.; Szekeres,L.; Papp,G.
参考来源:J Med Chem 1982,25(2),105-107