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【结 构 式】 
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【药物名称】Fantofarone, SR-33557 【化学名称】2-Isopropyl-1-[4-[3-[N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]amino]propoxy]phenylsulfonyl]indolizine 【CA登记号】114432-13-2 【 分 子 式 】C31H38N2O5S 【 分 子 量 】550.72291 |
【开发单位】Labaz (Originator), Sanofi-synthélabo (Originator) 【药理作用】Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, L-Type Calcium Channel Blockers |
合成路线1
This compound has been obtained by two similar ways: 1) The alkylation of 4-hydroxyphenyl(2-isopropylindolizin-1-yl)sulfone (I) 1,3-dibromopropane (II) by means of K2CO3 in DMF gives 4-(3-bromopropoxy)phenyl(2-isopropylindolizin-1-yl)sulfone (III), which is finally condensed with N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamine. 2) By direct condensation of sulfone (I) with the tertiary amine N-(3-chloropropyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamine.
| 【1】 Gubin, J.; et al.; A novel class of calcium-entry blockers: The 1-[[4-(aminoalkoxy)phenyl]sulfonyl]indolizines. J Med Chem 1992, 35, 6, 981. |
| 【2】 Gubin, J.; et al.; Novel heterocyclic analogues of the new potent class of calcium entry blockers: 1-[[4-(Aminoalkoxy)phenyl]sulfonyl]indolizines. J Med Chem 1993, 36, 10, 1425. |
| 【3】 Chatelain, P.; Gubin, J.; Aminoalkoxybenzenesulfonyl heterocyclic compounds, a novel class of calcium channel antagonists. Structure-activity relationship with a focus on fantofarone, SR 33557. Drugs Fut 1993, 18, 9, 817. |
| 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) | 41267 | 4-[(2-isopropyl-1-indolizinyl)sulfonyl]phenol | C17H17NO3S | 详情 | 详情 | |
| (II) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (III) | 41268 | 4-(3-bromopropoxy)phenyl 2-isopropyl-1-indolizinyl sulfone; 1-[[4-(3-bromopropoxy)phenyl]sulfonyl]-2-isopropylindolizine | C20H22BrNO3S | 详情 | 详情 | |
| (IV) | 29986 | 3-chloro-N-(3,4-dimethoxyphenethyl)-N-methyl-1-propanamine; N-(3-chloropropyl)-N-(3,4-dimethoxyphenethyl)-N-methylamine | C14H22ClNO2 | 详情 | 详情 | |
| (V) | 18938 | 2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine | 3490-06-0 | C11H17NO2 | 详情 | 详情 |