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【结 构 式】 
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【药物名称】SL-11093 【化学名称】trans-N1-Ethyl-N4-[2-[4-(ethylamino)butylaminomethyl]cyclopropylmethyl]-1,4-butanediamine tetrahydrochloride 【CA登记号】306292-64-8 【 分 子 式 】C17H42Cl4N4 【 分 子 量 】444.36309 |
【开发单位】SLIL Biomedical (Originator) 【药理作用】Oncolytic Drugs, Prostate Cancer Therapy, Apoptosis Inducers, Polyamine Biosynthesis Inhibitors |
合成路线1
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.
| 【2】 Marton, L.J.; Frydman, B. (SLIL Biomedical Corp.); Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases. WO 0066175 . |
| 【1】 Sarkar, A.; Basu, H.S.; Marton, L.J.; Valasinas, A.; Frydman, B.; Reddy, V.K.; Conformationally restricted analogues of 1N,14N-bisethylhomospermine (BE-4-4-4): Synthesis and growth inhibitory effects on human prostate cancer cells. J Med Chem 2001, 44, 3, 390. |
| 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) | 46925 | N-ethyl-2,4,6-trimethylbenzenesulfonamide | C11H17NO2S | 详情 | 详情 | |
| (II) | 34789 | 4-bromobutanenitrile | 5332-06-9 | C4H6BrN | 详情 | 详情 |
| (III) | 46926 | N-(3-cyanopropyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide | C15H22N2O2S | 详情 | 详情 | |
| (IV) | 46927 | N-(4-aminobutyl)-N-ethyl-2,4,6-trimethylbenzenesulfonamide | C15H26N2O2S | 详情 | 详情 | |
| (V) | 41158 | 2,4,6-trimethylbenzenesulfonyl chloride | 773-64-8 | C9H11ClO2S | 详情 | 详情 |
| (VI) | 46928 | N-ethyl-N-[4-[(mesitylsulfonyl)amino]butyl]-2,4,6-trimethylbenzenesulfonamide | C24H36N2O4S2 | 详情 | 详情 | |
| (VII) | 46929 | ((1R,2R)-2-[[(mesitylsulfonyl)oxy]methyl]cyclopropyl)methyl 2,4,6-trimethylbenzenesulfonate | C23H30O6S2 | 详情 | 详情 | |
| (VIII) | 46930 | N-ethyl-N-[4-[[((1R,2R)-2-[[[4-[ethyl(mesitylsulfonyl)amino]butyl](mesitylsulfonyl)amino]methyl]cyclopropyl)methyl](mesitylsulfonyl)amino]butyl]-2,4,6-trimethylbenzenesulfonamide | C53H78N4O8S4 | 详情 | 详情 |