Pictet-Spengler reaction of biogenic amines with carbohydrates. Synthesis of novel C-nucleosides
Pictet-Spengler reaction of biogenic amines with carbohydrates. Synthesis of novel C-nucleosides
复制标题
生物胺与碳水化合物的 Pictet-Spengler 反应。
DOI：
10.1139/v83-467
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发表时间：
1983
影响因子：
1.1
通讯作者：
W. Szarek
中科院分区：
文献类型：
--
作者：
I. M. Piper;D. Maclean;I. Kvarnström;W. Szarek
利用生物胺与碳水化合物的Pictet-Spengler缩合反应合成了几种新型的C-核苷。多巴胺盐酸盐与D-葡萄糖反应得到6，7-二羟基-1（R）-和-1（S）-（D-葡萄糖戊糖醇-1 ′-基）-1，2，3，4-四氢异喹啉盐酸盐，与2，5-脱水-D-甘露糖反应得到1（R）-和1（S）-（α-D-阿拉伯呋喃糖基）-6，7-二羟基-1，2，3，4-四氢异喹啉盐酸盐。盐酸色胺和组胺不与D-葡萄糖反应，而与2，5-脱水-D-甘露糖反应，分别生成1（R）-和1（S）-（α-D-阿拉伯呋喃糖基）-1，2，3，4-四氢-β-咔啉和4-（α-D-阿拉伯呋喃糖基）-咪唑并[4，5-c]-4，5，6，7-四氢吡啶。化合物的结构已通过核磁共振实验和质谱法确定。
Several novel C-nucleosides have been prepared by Pictet–Spengler condensations between biogenic amines and carbohydrates. Dopamine hydrochloride reacted with D-glucose to give 6,7-dihydroxy-1(R)- and -1(S)-(D-gluco-pentitol-1′-yl)-1,2,3,4-tetrahydroisoquinoline hydrochlorides, and with 2,5-anhydro-D-mannose to give 1(R)- and 1(S)-(α-D-arabinofuranosyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorides. Tryptamine hydrochloride and histamine did not react with D-glucose, but with 2,5-anhydro-D-mannose gave 1(R)- and 1(S)-(α-D-arabinofuranosyl)-1,2,3,4-tetrahydro-β-carboline and 4-(α-D-arabinofuranosyl)-imidazo[4,5-c]-4,5,6,7-tetrahydropyridine, respectively. The structures of the compounds have been established by nmr experiments and by mass spectrometry.