摘要
在相转移催化剂BnEt3N+Br-作用下,利用5-取代苯氧甲基-2-巯基-1,3,4-噻二唑与α-溴代四乙酰基吡喃糖室温反应,合成了22个结构新颖的硫代糖苷类SGLT2抑制剂化合物,结构经IR,1HNMR,13CNMR和HR-ESI-MS谱表征确认.采用小鼠口服葡萄糖耐受量法测定了目标化合物在治疗糖尿病方面的活性,结果发现化合物9Ah有明显的降糖作用,而9Aa和9Bi与对照药物格列齐特相当.
22 thioglycosides with novel structure were designed and synthesized from 5-substituded phenyloxymethyl-2-mercapto-1,3,4-thiadiazole and tetra-O-acetyl-α-glycopyranosyl bromides in the presence of phase transfer catalysis（BnEt3N^＋Br^-） at room temperature.These compounds were characterized by IR,^1H NMR,^13C NMR,and HR-ESI-MS techniques.Bioactivity of decreasing blood glucose was performed through in vivo by oral glucose tolerance test（OGTT） in mice.In addition,preliminary pharmacological test showed that compound 9Ah was more potent than positive control gliclazide,while compounds 9Aa and 9Bi were comparable to gliclazide in potency.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2010年第6期849-859,共11页
Chinese Journal of Organic Chemistry
基金
科技部支撑(No.2007BAI40B01)
天津市科技支撑计划重点(No.10ZCKFSH01300)资助项目
关键词
噻二唑
硫代糖苷
SGLT2抑制剂
合成
降糖活性
thiadiazole
thioglycoside
SGLT2 inhibitor
synthesis
anti-hyperglycemic activity
