Nocloprost, ZK 94 726, ZK-84726
诺氯前列素Chemical Name: (Z)-7-[(1R,2R,3R,5R)-5-Chloro-3-hydroxy-2-[(E)-(3R)-3-hydroxy-4,4-dimethyl-1-octenyl]cyclopentyl]-5-heptenoic acid; (9R,11R,15R)-9-Chloro-11,15-dihydroxy-16,16-dimethylprosta-5Z,13E-dienoic acid; 9-Chloro-9-deoxy-16,16-dimethylprostaglandin F2beta
CAS No. 79360-43-3
项目整合开发状态: Phase II
项目研究机构: Schering AG (Originator), Aventis Pharma (Licensee)
合成路线:Esterification of 16,16-dimethyl-PGF2alpha 11,15-bistetrahydropyranyl ether (I) with diazomethane followed by chlorination with tetrachloromethane and triphenylphosphine in the presence of triethylamine afforded the 9beta-chloro intermediate (II).Deprotection with acetic acid yielded the 11,15 diol (III),which was finally converted to nocloprost by treatment with potassium hydroxide in ethanol-water.
📌 参考资料/链接：
参考文献标题:Pharmaceutically active 9-chloroprostaglandins
文献作者:Elger,W.; Loge,O.; Skuballa,W.; Vorbr黦gen,H.; Radb點hel,B.; Schillinger,E.(Schering AG)
参考来源:DE 2950027; US 4444788; US 5079259
📄 详细内容
合成路线:Esterification of 16,16-dimethyl-PGF2alpha 11,15-bistetrahydropyranyl ether (I) with diazomethane followed by chlorination with tetrachloromethane and triphenylphosphine in the presence of triethylamine afforded the 9beta-chloro intermediate (II).Deprotection with acetic acid yielded the 11,15 diol (III),which was finally converted to nocloprost by treatment with potassium hydroxide in ethanol-water.
参考文献标题:Nocloprost
文献作者:Losert,W.; et al.
参考来源:Drugs Fut 1988,13(10),926
合成路线:Esterification of 16,16-dimethyl-PGF2alpha 11,15-bistetrahydropyranyl ether (I) with diazomethane followed by chlorination with tetrachloromethane and triphenylphosphine in the presence of triethylamine afforded the 9beta-chloro intermediate (II).Deprotection with acetic acid yielded the 11,15 diol (III),which was finally converted to nocloprost by treatment with potassium hydroxide in ethanol-water.
参考文献标题:Tertiares Phosphan/Tetrachlormethan,ein vielseitiges Reagenz zur Chlorierung,Dehydratisierung und PN-Verknupfung
文献作者:Appel,R.
参考来源:Angew Chem 1975,166(87),863
合成路线:Esterification of 16,16-dimethyl-PGF2alpha 11,15-bistetrahydropyranyl ether (I) with diazomethane followed by chlorination with tetrachloromethane and triphenylphosphine in the presence of triethylamine afforded the 9beta-chloro intermediate (II).Deprotection with acetic acid yielded the 11,15 diol (III),which was finally converted to nocloprost by treatment with potassium hydroxide in ethanol-water.
参考文献标题:Synthesis and biological properties of 16,16-alkylprostaglandins
文献作者:Magerlein,B.J.; Ducharme,D.W.; Magee,W.E.; Miller,W.L.; Robert,A.; Weels,J.R.
参考来源:Prostaglandins 1973,16(4),143
产品链接: CAS No. 79360-43-3››