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【结 构 式】 
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【药物名称】FPL-55712 【化学名称】7-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylic acid 【CA登记号】40786-08-1 (Na salt) 【 分 子 式 】C27H30O9 【 分 子 量 】498.53475 |
【开发单位】AstraZeneca (Originator) 【药理作用】Angina pectoris, Treatment of, Antiallergy/Antiasthmatic Drugs, Asthma Therapy, CARDIOVASCULAR DRUGS, RESPIRATORY DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Leukotriene Antagonists, Leukotriene Synthesis Inhibitors |
合成路线1
By condensation of ethyl 8-propyl-7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate (I) with 4-(2,3-epoxypropoxy)-3-propyl-2-hydroxyacetophenone (II) by means of benzyltrimethylammonium hydroxide in refluxing DMF, followed by hydrolysis with NaHCO3 in refluxing ethanol - water. The starting compounds (I) and (II) are prepared as follows: 1) The condensation of 3-propyl-2,4-dihydroxyacetophenone (III) with diethyl oxalate (IV) by means of sodium ethoxide in refluxing ethanol gives (I). 2) The condensation of acetophenone (III) with 1-chloro-2,3-epoxypropane (V) by means of KOH in refluxing ethanol - water gives (II).
| 【1】 Pratt, A.D.; Bantick, J..; Lee, T.B.; Chamberlain, T.R.; Hardern, D.N.; Appleton, R.A.; Antagonits of slow reacting substance od anaphylaxis. Synthesis of a series of chromone-2-carboxylic acids. J Med Chem 1979, 20, 3, 371. |
| 【2】 Augstein, J.; Lee, T.B.; Carter, D. (AstraZeneca plc); Chromone derivs.. FR 2147287 . |
| 【3】 Augstein, J.; Carter, D.; Lee, T.B. (AstraZeneca plc); Chrome cpds. having SRS-A properties. US 3882148 . |
| 【4】 Blancafort, P.; Castaner, J.; Sneddon, J.M.; Serradell, M.N.; FPL-55,712. Drugs Fut 1982, 7, 7, 472. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 37126 | C10H18NO | 详情 | 详情 | |||
| (I) | 37124 | ethyl 7-hydroxy-4-oxo-8-propyl-4H-chromene-2-carboxylate | C15H16O5 | 详情 | 详情 | |
| (II) | 37125 | 1-[2-hydroxy-4-(2-oxiranylmethoxy)-3-propylphenyl]-1-ethanone | C14H18O4 | 详情 | 详情 | |
| (III) | 13137 | 2',4'-Dihydroxy-3'-propylacetophenone; 1-(2,4-Dihydroxy-3-propylphenyl)-1-ethanone | 40786-69-4 | C11H14O3 | 详情 | 详情 |
| (IV) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (V) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |