SL-11047
N,N'-双[3-(乙氨基)丙基]-2(Z)-丁烯-1,4-二胺四盐酸盐Chemical Name: N,N'-Bis[3-(ethylamino)propyl]-2(Z)-butene-1,4-diamine tetrahydrochloride
CAS No. 206991-64-2, 308145-19-9 (free base)
项目整合开发状态: Phase I/II
项目研究机构: SLIL Biomedical (Originator)
合成路线:The title tetraamino derivative was prepared by two related methods.Conversion of cis-butenediol (I) into the diamine (II) was effected by Mitsunobu condensation of (I) with HN3 with concomitant reduction of the azido group in the presence of PPh3.Acylation of (II) with mesitylenesulfonyl chloride (III) provided the bis-sulfonamide (IV),which was subsequently alkylated with the bromosulfonamide (V) in the presence of NaH to furnish the protected tetraamine (VI).The sulfonamido groups of (VI) were finally hydrolyzed by an HOAc solution of HBr in the presence of phenol.
合成路线:Alternatively,diol (I) was converted to the bis-sulfonate ester (VII) under phase-transfer conditions.Alkylation of the sodium salt of N-ethyl-1,3-propanediamine disulfonamide (VIII) with the bis-mesytilate (VII) produced (VI),which was then deprotected as above.
📌 参考资料/链接：
参考文献标题:Conformationally restricted polyamines
文献作者:Witiak,D.T.; Frydman,B.J.; Marton,L.J.; Reddy,V.K.; Valasinas,A.L.(Wisconsin Alumni Research Foundation)
参考来源:US 5889061
📄 详细内容
合成路线:The title tetraamino derivative was prepared by two related methods.Conversion of cis-butenediol (I) into the diamine (II) was effected by Mitsunobu condensation of (I) with HN3 with concomitant reduction of the azido group in the presence of PPh3.Acylation of (II) with mesitylenesulfonyl chloride (III) provided the bis-sulfonamide (IV),which was subsequently alkylated with the bromosulfonamide (V) in the presence of NaH to furnish the protected tetraamine (VI).The sulfonamido groups of (VI) were finally hydrolyzed by an HOAc solution of HBr in the presence of phenol.
合成路线:Alternatively,diol (I) was converted to the bis-sulfonate ester (VII) under phase-transfer conditions.Alkylation of the sodium salt of N-ethyl-1,3-propanediamine disulfonamide (VIII) with the bis-mesytilate (VII) produced (VI),which was then deprotected as above.
参考文献标题:Conformationally restricted polyamines and their use as antineoplastic agents
文献作者:Witiak,D.T.; Frydman,B.J.; Marton,L.J.; Reddy,V.K.; Valasinas,A.L.(Wisconsin Alumni Research Foundation)
参考来源:JP 2002508739; WO 9817624
合成路线:Alternatively,diol (I) was converted to the bis-sulfonate ester (VII) under phase-transfer conditions.Alkylation of the sodium salt of N-ethyl-1,3-propanediamine disulfonamide (VIII) with the bis-mesytilate (VII) produced (VI),which was then deprotected as above.
参考文献标题:Conformationally restricted analogues of 1N,12N-bisethylspermine: Synthesis and growth inhibitory effects on human tumor cell lines
文献作者:Reddy,V.K.; Valasinas,A.; Sarkar,A.; Basu,H.S.; Marton,L.J.; Frydman,B.
参考来源:J Med Chem 1998,41(24),4723
产品链接: CAS No. 206991-64-2›› 产品链接: CAS No.308145-19-9››