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【结 构 式】

【药物名称】NSC-95466, PCNU

【化学名称】1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitrosourea
      N-(2-Chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitrosourea

【CA登记号】13909-02-9

【 分 子 式 】C8H11ClN4O4

【 分 子 量 】262.65427

【开发单位】National Cancer Institute (Originator), Pfizer (Originator), Southern Research Institute (Originator)

【药理作用】Oncolytic Drugs, DNA-Damaging Drugs

合成路线1

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.

1 Johnston, T.P.; et al.; The synthesis of potential anticancer agents. XXXVI. N-Nitrosoureas. II. Haloalkyl derivatives. J Med Chem 1966, 9, 6, 892-911.
2 Woodman, R.J.; Castaner, J.; PCNU. Drugs Fut 1981, 6, 8, 481.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 37578 N(2)-[(benzyloxy)carbonyl]glutamine C13H16N2O5 详情 详情
(II) 37579 methyl 5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoate C14H18N2O5 详情 详情
(III) 37575 benzyl 2,6-dioxo-3-piperidinylcarbamate C13H14N2O4 详情 详情
(IV) 37576 3-amino-2,6-piperidinedione;3-aminopiperidine-2,6-dione;2-amino-Glutarimide;Glutamimide;a-Aminoglutarimide 2353-44-8 C5H8N2O2 详情 详情
(V) 11237 1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate 1943-83-5 C3H4ClNO 详情 详情
(VI) 37577 N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)urea C8H12ClN3O3 详情 详情
Extended Information