摘要
目的 :对位取代苯酚氧苷类化合物具有多种生物活性 ,在对对位取代苯酚氧苷类化合物结构 活性研究中 ,我们进行了对乙酰氨基酚葡萄糖苷及其类似物的合成工作。方法 :采用相转移催化合成法 ,由溴代葡萄糖与对羟基苯酚合成了对硝基苯基葡萄糖苷 ,再经 5 %Pd C催化氢化还原为氨基苯基葡萄糖苷 ,然后经氨基酰化、脱乙酰基得到对乙酰氨基酚葡萄糖苷。采用常规方法制得其类似物。结果 :从葡萄糖计算 ,对乙酰氨基酚四乙酰葡萄糖苷总收率为 4 6 0 % ,所得到的产物的结构经1HNMR、IR、元素分析证实。结论 :该方法为首次报道此化合物及其类似物的合成方法 。
AIM:p-Substituted phenyl-β-D-glucosides have numerous biological activities To investigate the structure-activity relationship of them,4-aminophenol-glucopyranoside and its analogues were synthesized METHOD:4-Nitrophenyl- 2′,3′,4′,6′-aceglucopyranoside was synthesized from 2′,3′,4′,6′- aceglucose bromide and 4-nitrophenol by phase-transfer catalysis 4-Nitrophenyl-2′,3′,4′,6′-aceglucopyranoside was reduced to 4-aminophenol-2′,3′,4′,6′- aceglucopyranoside under catalytic transfer hydrogenation with 5% Pd on charcoal Finally,4-aceaminophenol- glucopyranoside was easily derived by deactylation from 2′,3′,4′,6′-aceglucopyranoside obtained by acetylation Its analogues were obtained by common method RESULT:Starting from glucose,4-aminophenol-glucopyranoside was synthesized with 46 0% yields Structures of the resultants were identified by 1 HNMR ,IR and elemental analysis CONCLUSION:The synthesis method of 4-aminophenol-glucopyranoside and its analogues was reported for the first time The pharmacological study is under study and forthcoming
出处
《中国药科大学学报》
CAS
CSCD
北大核心
2004年第5期397-400,共4页
Journal of China Pharmaceutical University
关键词
对乙酰氨基酚
葡萄糖苷
合成
对乙酰氨基酚葡萄糖苷
相转移催化
催化氢化
Paracetamol
Glucopyranoside
Synthesis
4-Aminophenol-glucopyranoside
Phase-transfer catalysis
Catalytic transfer hydrogenation
