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Nafidimide, Amonafide, CGX-571, M-FA-142, BIDA, NSC-308847, Xanafide, Quinamed

氨萘非特Chemical Name: 3-Amino-N-[2-(dimethylamino)ethyl]naphthalimide; 5-Amino-2-[2-(dimethylamino)ethyl]-1H-benz[d,e]isoquinoline-1,3(2H)-dione
CAS No. 69408-81-7
项目整合开发状态: Phase II
项目研究机构: Abbott (Originator), ChemGenex Pharmaceuticals (Not Determined), Xanthus (Not Determined)
合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)
📌 参考资料/链接:
参考文献标题:Naphthalimides,process for their preparation and pharmaceutical compositions containing them
文献作者:Bra馻,M.F.; Martinez Sanz,A.; P閞ez Alvarez-Ossorio,R.; Martinez Roldan,C.; Rodan Fernandez de Gamboa,C.(Made Labs.)
参考来源:DE 2823987

📄 详细内容


合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)

参考文献标题:Substd.benzylamine derivs.and methods of use
文献作者:Nishimura,N.; Askew,B.; Patel,V.F.; Elbaum,D.; Habgood,G.; Kim,J.L.; Handley,M.; Booker,S.; Germain,J.; Kim,T.-S.; Yuan,C.C.(Amgen Inc.)
参考来源:US 2003134836; WO 0407457


合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)

参考文献标题:Synthesis and cytostatic activity of benz(de)isoquinolin-1,3-diones.Structure-activity relationships
文献作者:Fern醤dez Bra馻,M.; Mart韓ez Sanz,A.; Castellano,J.M.; Mart韓ez Roldan,C.; Roldan Fern醤dez de Gamboa,C.
参考来源:Eur J Med Chem - Chim Ther 1981,16(3),207-212


合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)

合成路线:Nitration of 1,8-naphthalic anhydride (I) in sulfuric acid at 60 C for 1 h gives 3,6-dinitro-1,8-naphthalic anhydride (II) in 80% yield (m.p.209-211 C from toluene; NMR: in CDCl3 a 9.22,9.27,2 singlet aromatic H),which,on treatment with unsym-N,N-dimethylethylenediamine at room temperature for 30 min,followed by azeotropical removal of water at 140 C for 2 h in refluxing toluene solution and salt conversion with HCl,yields the monohydrochloride salt of dinimide in 62% yield.

参考文献标题:N-(Aminoalkyl)imide antineoplastic agents.Synthesis and biological activity
文献作者:Zee-Cheng,R.K.Y.; Cheng,C.C.
参考来源:J Med Chem 1985,28(9),1216-22


合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)
参考文献标题:Amonafide
文献作者:Castar,J.; Castar,R.M.; Eastland,G.
参考来源:Drugs Fut 1990,15(9),879


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