新产品编号:918069
Chemical Name: N-[4-[Bis(2-chloroethyl)amino]phenyl]-N'-[2-(4-hydroxyphenyl)ethyl]urea
CAS No. 393511-88-1
项目整合开发状态: Biological Testing
项目研究机构: Imperial Coll. of Sci., Technol. & Med. (Originator), University of Reading (Originator)
合成路线:Coupling of tyramine (I) with p-nitrophenyl isocyanate (II) affords urea (III).Subsequent nitro group reduction with H2 and Pd/C gives amine (IV).Condensation of amine (IV) with ethylene oxide (V) leads to the bis-hydroxyethyl amine (VI).This is finally chlorinated employing SOCl2 in pyridine.Alternatively,amine (IV) is subjected to reductive alkylation with chloroacetaldehyde and NaBH3CN to furnish the target bis-chloroethyl amine.(1,2)
📌 参考资料/链接：
参考文献标题:Phenylethylamine derivs.and their use in the treatment of melanoma
文献作者:Riley,P.A.; Photiou,A.; Khan,T.H.; Osborn,H.M.I.; Malkin,H.
参考来源:EP 1303481; WO 0208174
📄 详细内容
合成路线:Coupling of tyramine (I) with p-nitrophenyl isocyanate (II) affords urea (III).Subsequent nitro group reduction with H2 and Pd/C gives amine (IV).Condensation of amine (IV) with ethylene oxide (V) leads to the bis-hydroxyethyl amine (VI).This is finally chlorinated employing SOCl2 in pyridine.Alternatively,amine (IV) is subjected to reductive alkylation with chloroacetaldehyde and NaBH3CN to furnish the target bis-chloroethyl amine.(1,2)
合成路线:In an alternative method,p-nitroaniline (I) is reacted with ethylene oxide (II) to afford diol (III).This compound can also be prepared by condensation of 1-fluoro-4-nitrobenzene (IV) with diethanolamine (V).Chlorination of diol (III) to provide (VI) is accomplished with either mesyl chloride or SOCl2 in the presence of pyridine.Then,nitro group reduction in (VI) by means of iron and HCl affords aniline (VII).
合成路线:Reaction of tyramine (VIII) with p-nitrophenyl chloroformate (IX) gives rise to the nitrophenyl carbamate (X).Finally,coupling of (X) with aniline (VII) provides the title urea.
参考文献标题:Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)
文献作者:Jordan,A.M.; Khan,T.H.; Malkin,H.; Osborn,H.M.I.
参考来源:Bioorg Med Chem 2002,10(8),2625