GNTI
5′-胍基诺曲因多尔二(三氟乙酸盐)盐水合物 Chemical Name: 17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxy-5'-guanidino-6,7-didehydroindolo[2',3':6,7]morphinan; N-[(4bS,8R,8aS,14bR)-7-(Cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-11-yl]guanidine
CAS No. 219655-56-8, 219655-57-9 (trifluoroacetate)
项目整合开发状态: Preclinical
项目研究机构: University of Minnesota (Originator)
合成路线:Fischer indole cyclization of naltrexone (I) with 4-nitrophenylhydrazine (II) provided 5'-nitronaltrindole (III).Subsequent reduction of the nitro group of (III) by means of hydrazine hydrate and Raney Nickel gave the 5'-amino derivative (IV).Mercury-assisted condensation of (IV) with di(tert-butoxy-carbonyl)thiourea (V) afforded the protected guanidine (VI).Finally,the Boc groups of (VI) were cleaved by treatment with trifluoroacetic acid to furnish the title compound.
📌 参考资料/链接：
参考文献标题:Naltrindole analogs as potent and selective kappa-opioid receptor antagonists
文献作者:Sercel,A.D.; Stevens,W.C.Jr.; Ingals,S.; et al.
参考来源:218th ACS Natl Meet (Aug 22 1999,New Orleans) 1999,Abst MEDI 267
📄 详细内容
合成路线:Fischer indole cyclization of naltrexone (I) with 4-nitrophenylhydrazine (II) provided 5'-nitronaltrindole (III).Subsequent reduction of the nitro group of (III) by means of hydrazine hydrate and Raney Nickel gave the 5'-amino derivative (IV).Mercury-assisted condensation of (IV) with di(tert-butoxy-carbonyl)thiourea (V) afforded the protected guanidine (VI).Finally,the Boc groups of (VI) were cleaved by treatment with trifluoroacetic acid to furnish the title compound.
参考文献标题:Mutational evidence for a common kappa antagonist binding pocket in the wild-type kappa and mutant mu[K303E] opioid receptors
文献作者:Jones,R.M.; Hjorth,S.A.; Schwartz,T.W.; Portoghese,P.S.
参考来源:J Med Chem 1998,41(25),4911
合成路线:Fischer indole cyclization of naltrexone (I) with 4-nitrophenylhydrazine (II) provided 5'-nitronaltrindole (III).Subsequent reduction of the nitro group of (III) by means of hydrazine hydrate and Raney Nickel gave the 5'-amino derivative (IV).Mercury-assisted condensation of (IV) with di(tert-butoxy-carbonyl)thiourea (V) afforded the protected guanidine (VI).Finally,the Boc groups of (VI) were cleaved by treatment with trifluoroacetic acid to furnish the title compound.
合成路线:Fischer indole cyclization of naltrexone (I) with 4-(cyanomethyl)phenylhydrazine (II) produces the indolomorphinan derivative (III).Subsequent reduction of the cyano group of (III) by catalytic hydrogenation over Raney-nickel produces amine (IV).This is then condensed with methyl acetimidate (V) to furnish the corresponding amidine.
参考文献标题:Potent and selective indolomorphinan antagonists of the kappa-opioid receptor
文献作者:Stevens,W.C.; Jones,R.M.; Subramanian,G.; Metzger,T.G.; Ferguson,D.M.; Portoghese,P.S.
参考来源:J Med Chem 2000,43(14),2759
产品链接: CAS No. 219655-56-8›› 产品链接: CAS No.219655-57-9››