SC-41930
2H-1-苯并吡啶-2-羧酸,7-[3-(4-乙酰-3-甲氧基-2-丙基苯氧基)丙氧]-3,4-二氢-8-丙基-Chemical Name: 7-[3-(4-Acetyl-3-methoxy-2-propylphenoxy)propoxy]-8-propyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
CAS No. 120072-59-5
项目整合开发状态: Phase II
项目研究机构: Pfizer (Originator), Kureha (Licensee)
合成路线:The reaction of 2,4-dihydroxy-3-n-propylacetophenone (I) with excess 1,3-dibromopropane in the presence of potassium carbonate in dimethylformamide gives 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (II).Subsequent reaction of (II) with 2-carbomethoxy-7-hydroxy-8-n-propylchromone in dimethylformamide containing anhydrous potassium carbonate furnished 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchromone (III),m.p.113-115 C.Hydrogenation of (III) in acetic acid with 5% palladium on carbon catalyst generated 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchroman (IV),m.p.70-72 C.Subsequent alkylation of (IV) with excess methyl iodide in refluxing acetone containing anhydrous potassium carbonate produced O-methyl ester (V).Final hydrolysis of O-methyl ester (V) was carried out with lithium hydroxide in aqueous methanol to provide SC-41930.
📌 参考资料/链接：
参考文献标题:7-[3-(4-Acetyl-3-methoxy-2-propylphenoxy)propoxy]-3,4-dihydro-8-propyl- 2H-1-benzopyran-2-carboxylic acid: An orally active selective leukotriene B4 receptor antagonist
文献作者:Djuric,S.W.; Collins,P.W.; Jones,P.H.; et al.
参考来源:J Med Chem 1989,32(6),1145-7
📄 详细内容
合成路线:The reaction of 2,4-dihydroxy-3-n-propylacetophenone (I) with excess 1,3-dibromopropane in the presence of potassium carbonate in dimethylformamide gives 3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (II).Subsequent reaction of (II) with 2-carbomethoxy-7-hydroxy-8-n-propylchromone in dimethylformamide containing anhydrous potassium carbonate furnished 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchromone (III),m.p.113-115 C.Hydrogenation of (III) in acetic acid with 5% palladium on carbon catalyst generated 2-carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)propoxy]-8-n-propylchroman (IV),m.p.70-72 C.Subsequent alkylation of (IV) with excess methyl iodide in refluxing acetone containing anhydrous potassium carbonate produced O-methyl ester (V).Final hydrolysis of O-methyl ester (V) was carried out with lithium hydroxide in aqueous methanol to provide SC-41930.
参考文献标题:SC-41930
文献作者:Shone,R.L.; Djuric,S.W.; Tsai,B.S.; Fretland,D.J.; Gaginella,T.S.; Cook,C.S.
参考来源:Drugs Fut 1990,15(7),695
产品链接: CAS No. 120072-59-5››