NSC-95466, PCNU
1-(2-氯乙基)-3-(2,6-二氧代-3-哌啶基)-1-亚硝基脲Chemical Name: 1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitrosourea; N-(2-Chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitrosourea
CAS No. 13909-02-9
项目整合开发状态: Phase III
项目研究机构: National Cancer Institute (Originator), Pfizer (Originator), Southern Research Institute (Originator)
合成路线:The esterification of N2-(benzyloxycarbonyl)-D,L-glutamine (I) with methyl iodide and KHCO3 in DMF gives the corresponding methyl ester (II),which is cyclized to benzyl D,L-2,6-dioxo-3-piperidinecarbamate (III) by heating.The hydrogenolysis of (III) with H2 over Pd/C in methanol yields D,L-2-aminoglutarimide (IV),which is condensed with 2-chloroethyl isocyanate (V) in DMF affording 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)urea (VI).Finally,this compound is nitrosated in the usual way with NaNO2 in formic acid.
📌 参考资料/链接：
参考文献标题:PCNU
文献作者:Woodman,R.J.; Castar,J.
参考来源:Drugs Fut 1981,6(8),481
📄 详细内容
合成路线:The esterification of N2-(benzyloxycarbonyl)-D,L-glutamine (I) with methyl iodide and KHCO3 in DMF gives the corresponding methyl ester (II),which is cyclized to benzyl D,L-2,6-dioxo-3-piperidinecarbamate (III) by heating.The hydrogenolysis of (III) with H2 over Pd/C in methanol yields D,L-2-aminoglutarimide (IV),which is condensed with 2-chloroethyl isocyanate (V) in DMF affording 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)urea (VI).Finally,this compound is nitrosated in the usual way with NaNO2 in formic acid.
参考文献标题:The synthesis of potential anticancer agents.XXXVI.N-Nitrosoureas.II.Haloalkyl derivatives
文献作者:Johnston,T.P.; McCaleb,G.S.; Opliger,P.S.; Montgomery,J.A.
参考来源:J Med Chem 1966,9(6),892-911
产品链接: CAS No. 13909-02-9››