SL-11093
Chemical Name: trans-N1-Ethyl-N4-[2-[4-(ethylamino)butylaminomethyl]cyclopropylmethyl]-1,4-butanediamine tetrahydrochloride; trans-1,2-Bis[4-(ethylamino)butylaminomethyl]cyclopropane tetrahydrochloride
CAS No. 306292-64-8
项目整合开发状态: Preclinical
项目研究机构: SLIL Biomedical (Originator)
合成路线:Alkylation of N-ethyl mesitylenesulfonamide (I) with 4-bromobutyronitrile (II) in the presence of NaH afforded the cyano sulfonamide (III).After catalytic hydrogenation of the cyano group of (III),the resulting amine (IV) was acylated with mesitylenesulfonyl chloride (V) to give the bis-sulfonamide (VI) (1).Subsequent condensation of (VI) with the bis-sulfonate (VII) produced the tetra-sulfonamide (VIII).Finally,cleavage of the mesitylenesulfonyl protecting groups of (VIII) using HBr in HOAc furnished the corresponding tetraamine,which was isolated as the hydrochloride salt.
📌 参考资料/链接：
参考文献标题:Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases
文献作者:Marton,L.J.; Frydman,B.(SLIL Biomedical Corp.)
参考来源:WO 0066175
📄 详细内容
合成路线:Alkylation of N-ethyl mesitylenesulfonamide (I) with 4-bromobutyronitrile (II) in the presence of NaH afforded the cyano sulfonamide (III).After catalytic hydrogenation of the cyano group of (III),the resulting amine (IV) was acylated with mesitylenesulfonyl chloride (V) to give the bis-sulfonamide (VI) (1).Subsequent condensation of (VI) with the bis-sulfonate (VII) produced the tetra-sulfonamide (VIII).Finally,cleavage of the mesitylenesulfonyl protecting groups of (VIII) using HBr in HOAc furnished the corresponding tetraamine,which was isolated as the hydrochloride salt.
参考文献标题:Conformationally restricted analogues of 1N,14N-bisethylhomospermine (BE-4-4-4): Synthesis and growth inhibitory effects on human prostate cancer cells
文献作者:Valasinas,A.; Sarkar,A.; Reddy,V.K.; Marton,L.J.; Basu,H.S.; Frydman,B.
参考来源:J Med Chem 2001,44(3),390
产品链接: CAS No. 306292-64-8››