摘要
Mollincdine(1-(3,4-亚甲二氧基苄基)-6,7-亚甲二氧基异喹啉)是花菱草碱的去甲游离碱。具有对抗多种实验性心律失常作用,Mollinedine全合成曾由Schlitter完成,本文对该路线作了改进,以苯甲酸、甘氨酸及胡椒醛为原料,经10步反应全合成Mollinedine。产品的熔点,红外光谱、质谱及核磁共振谱数据均与文献报道一致。
It was reported that Mollinedine, a benzylisoquinoline compound in Eschscholtzia Oregane, could prevent several experimental arrhythmias. In this paper we synthesized Mollinedine via 10 steps, using benzoic acid, glycine and piperonal as starting materials. Condensation of hippuric acid ( Ⅱ ) with poperonal yielded 2-phenyl-4-poperonylidene-5-oxazolone (Ⅲ), which was hydrolyzed by 1% K2CO3 to form N-benzoyl-C-piperonylidene glycine (Ⅳ), Ⅳ reacted with ammonia liquor in a Parr Shaker yielded a diamide (Ⅴ), and Ⅴ after hydrolysis gave N-(3,4-methylenedioxyphenylacetyl)-poperony glycine (Ⅵ). Esterifecation of 1 by methyl alcohlo and cone. H2SO4 yielded (Ⅶ). Cyclization of Ⅶ gave a dihydroisoquinoline-3-carboxylic ester(Ⅷ), Ⅷ was hydrolyzed to its free acid(Ⅸ). Mollinedine(Ⅹ) was obtained after decarboxy-lation and dehydrogenation of Ⅸ .The structure of synthesized Mollinedine was confirmed by IR NMR and MS spectra.
出处
《同济医科大学学报》
CAS
CSCD
北大核心
1992年第4期265-267,共3页
Acta Universitatis Medicinae Tongji
关键词
全合成
抗心律失常药
mollinedine
antiarrhythmic
total synthesis
