Nafetolol, K-5407
萘非洛尔Chemical Name: 8-[3-(tert-Butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol
CAS No. 42050-23-7, 42050-24-8 (hydrochloride)
项目整合开发状态: Biological Testing
项目研究机构:
合成路线:The selective methylation of 5,6,7,8-tetrahydro-5,8-ethanonaphthalene-1,4-diol (I) with dimethylsulfate in a two phase system gives 4-methoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (II),which is condensed with epichlorohydrin (III) by means of piperidine at 100 C yielding 1-methoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (IV).The reaction of (IV) with tert-butylamine (V) at 100 C affords 1-methoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VI),which is finally demethylated by treatment with pyridine hydrochloride at 160 C
合成路线:The selective hydrolysis of 1,4-diacetoxy-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII) with diethylamine in methanol gives 4-acetoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (VIII),which is condensed with epichlorohydrin (III) by means of piperidine at 90 C to afford 1-acetoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII).The reaction of (IX) with tert-butylamine (V) in refluxing toluene gives 1-acetoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (X),which is finally hydrolyzed with dry HCl in refluxing methanol
📌 参考资料/链接：
参考文献标题:Nafetolol
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; McGillion,F.B.
参考来源:Drugs Fut 1981,6(2),92
📄 详细内容
合成路线:The selective methylation of 5,6,7,8-tetrahydro-5,8-ethanonaphthalene-1,4-diol (I) with dimethylsulfate in a two phase system gives 4-methoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (II),which is condensed with epichlorohydrin (III) by means of piperidine at 100 C yielding 1-methoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (IV).The reaction of (IV) with tert-butylamine (V) at 100 C affords 1-methoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VI),which is finally demethylated by treatment with pyridine hydrochloride at 160 C
参考文献标题:Targeting MMP-7 via antisense oligonucleotide shows anti-metastatic effects in a colon cancer murine model
文献作者:Momiyama,N.; Ichikawa,Y.; Hasegawa,S.; Ishikawa,T.; Matsuyama,R.; Miazaki,K.; Shimada,H.
参考来源:Eur J Med Chem 1974,9(5),501
合成路线:The selective hydrolysis of 1,4-diacetoxy-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII) with diethylamine in methanol gives 4-acetoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (VIII),which is condensed with epichlorohydrin (III) by means of piperidine at 90 C to afford 1-acetoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VII).The reaction of (IX) with tert-butylamine (V) in refluxing toluene gives 1-acetoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (X),which is finally hydrolyzed with dry HCl in refluxing methanol
参考文献标题:
文献作者:Lauria,F.; et al.(Carlo Erba,S.p.A.)
参考来源:BE 790188; CA 992983; CH 565741; DE 2251095; FR 2157897; GB 1351557; JP 7349750; NL 7214106; ZA 7207459
产品链接: CAS No. 42050-23-7››