【结 构 式】 |
【药物名称】AS-2646, AD-2646 【化学名称】2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline dimaleate 【CA登记号】94788-64-4, 72320-60-6 (diHCl), 72320-59-3 (free base) 【 分 子 式 】C29H31N3O8 【 分 子 量 】549.58572 |
【开发单位】Dainippon Pharmaceutical (Originator) 【药理作用】Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS |
合成路线1
This compound can be prepared by two related ways: 1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II), which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III). The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV), which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V). The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI), which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII). Finally, this compound is condensed with N-ethylpiperazine (VIII) at 130 C. 2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X), which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.
【1】 Uno, H.; Nagai, Y.; Karasawa, T.; Furukawa, K. (Dainippon Pharm. Co.; Ltd.); 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its salts with acids, process for their preparation and their use as antidepressant agents. DE 2912414 . |
【2】 Uno, H.; Nagai, Y.; Hino, K.; Kawashima, K.; Oka, M.; Matsumoto, J.; A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines. Chem Pharm Bull 1989, 37, 1, 110. |
【3】 Prous, J.; Castaner, J.; AD-2646. Drugs Fut 1989, 14, 8, 735. |
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) | 20951 | 2-nitrobenzoic acid;o-Nitrobenzoic acid | 552-16-9 | C7H5NO4 | 详情 | 详情 |
(II) | 21099 | o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride | 610-14-0 | C7H4ClNO3 | 详情 | 详情 |
(III) | 21100 | (2-nitrophenyl)(phenyl)methanone | 2243-79-0 | C13H9NO3 | 详情 | 详情 |
(IV) | 21101 | (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone | 2835-77-0 | C13H11NO | 详情 | 详情 |
(V) | 21102 | N-(2-benzoylphenyl)acetamide | 85-99-4 | C15H13NO2 | 详情 | 详情 |
(VI) | 21103 | 4-phenyl-2(1H)-quinolinone | C15H11NO | 详情 | 详情 | |
(VII) | 21104 | 2-chloro-4-phenylquinoline | C15H10ClN | 详情 | 详情 | |
(VIII) | 14213 | N-Ethylpiperazine; 1-Ethylpiperazine | 5308-25-8 | C6H14N2 | 详情 | 详情 |
(IX) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
(X) | 21107 | 4-phenyl-2-(1-piperazinyl)quinoline | C19H19N3 | 详情 | 详情 |