【结 构 式】 |
【药物名称】Nicainoprol, RU-42924, CAS-924 【化学名称】(±)-1,2,3,4-Tetrahydro-8-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-1-(3-pyridinylcarbonyl)quinoline 【CA登记号】76252-06-7 【 分 子 式 】C21H27N3O3 【 分 子 量 】369.46764 |
【开发单位】Aventis Pharma (Originator), Cassella (Originator) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS |
合成路线1
The acylation of 8-hydroxy-1,2,3,4-tetrahydroquinoline (I) with nicotinoyl chloride (II) by means of triethylamine in benzene gives 8-hydroxy-1-nicotinoyl-1,2,3,4-tetrahydroquinoline (III), which is condensed with epichlorohydrin (IV) by means of potassium tert-butoxide in DMF to yield 1-nicotinoyl-8-(2,3-epoxy-1-propoxy)-1,2,3,4-tetrahydroquinoline (V). Finally, this compound is condensed with isopropylamine (VI) in ethanol.
【1】 Graewinger, O.; Raabe, T.; Beyerle, R.; Scholtholt, J.; Nitz, R.E.; 1-Acyl-8-(3-amino-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolines, compositions and use. DD 153368; DE 2934609; EP 0025864; JP 56034668; US 4335123 . |
【2】 Castaner, J.; Serradell, M.N.; Hillier, K.; Nicainoprol. Drugs Fut 1984, 9, 10, 749. |
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) | 16022 | 1,2,3,4-tetrahydro-8-quinolinol | C9H11NO | 详情 | 详情 | |
(II) | 10753 | Nicotinoyl chloride | C6H4ClNO | 详情 | 详情 | |
(III) | 34334 | [8-hydroxy-3,4-dihydro-1(2H)-quinolinyl](3-pyridinyl)methanone | C15H14N2O2 | 详情 | 详情 | |
(IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
(V) | 34335 | [8-(2-oxiranylmethoxy)-3,4-dihydro-1(2H)-quinolinyl](3-pyridinyl)methanone | C18H18N2O3 | 详情 | 详情 | |
(VI) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |