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【结 构 式】

【药物名称】Ensaculin hydrochloride, Anseculin hydrochloride, KA-672.HCl

【化学名称】7-Methoxy-6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3,4-dimethyl-2H-1-benzopyran-2-one hydrochloride

【CA登记号】155773-59-4 (free base)

【 分 子 式 】C26H33ClN2O5

【 分 子 量 】489.01631

【开发单位】Schwabe (Originator)

【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Acetylcholinesterase Inhibitors, NMDA Antagonists

合成路线1

As shown in Scheme 21591401a, the Pechmann reaction of 2-methoxy-hydroquinone (I) with 2-methyl-3-oxobutanoic acid ethyl ester (II) in 75% sulfuric acid gives 6-hydroxy-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one (III), which is condensed with 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazin (IV) in the presence of K2CO3 and KI in ethanol yielding the target product as free base.

1 Noldner, M.; Hauer, H.; Chatterjee, S.S.; Anseculin Hydrochloride. Drugs Fut 1996, 21, 8, 779.
2 Chatterjee, S.S.; Noldner, M.; Hauer, H. (Willmar Schwabe GmbH); Benzopyranones, a method for producing them and uses therefor. DE 4111861; JP 1994506922; US 5428038; WO 9218493 .
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) 16845 2-methoxy-1,4-benzenediol 824-46-4 C7H8O3 详情 详情
(II) 10362 ethyl 2-methyl-3-oxobutanoate; ethyl 2-methylacetoacetate 609-14-3 C7H12O3 详情 详情
(III) 16847 6-hydroxy-7-methoxy-3,4-dimethyl-2H-chromen-2-one C12H12O4 详情 详情
(IV) 16848 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine; 2-[4-(3-chloropropyl)piperazino]phenyl methyl ether C14H21ClN2O 详情 详情
Extended Information