5-羟甲基-2-呋喃甲醛衍生物的合成及降血糖活性评价  

Synthesis and hypoglycemic activity of 5-hydroxylmethyl-2-furfural derivatives

作　　者：张欣[1] 廖祥伟[2] 吴松[2] 杜冠华[2] 郝玲花[2] 

机构地区：[1]内蒙古医学院药学院,内蒙古呼和浩特010059 [2]中国医学科学院北京协和医学院药物研究所卫生部天然药物生物合成重点实验室,活性物质的发现与适药化研究北京市重点实验室,北京100050

出　　处：《中国药物化学杂志》2012年第5期349-355,共7页Chinese Journal of Medicinal Chemistry

基　　金：“十二五”重大新药创制科技重大专项(2012ZX09301002-001)

摘　　要：目的设计合成5-羟甲基-2-呋喃甲醛(5-HMF)衍生物,并评价其降血糖活性,寻找新型降血糖化合物。方法以5-羟甲基-2-呋喃甲醛为起始原料,分别经缩合、酯化、苄基化、脱苄基等反应合成目标化合物。通过测试目标化合物对葡萄糖促吸收率的影响评价化合物的活性。结果合成了14个未见文献报道的新化合物,其化学结构经1H-NMR、MS谱确证。结论生物活性评价结果显示,8个目标化合物(1～7、14)具有良好的降血糖活性,其中,化合物6的降血糖活性最好,其葡萄糖促吸收率为87.45%。5-Hydroxylmethyl-2-furfural （5-HMF） is the active ingredient of traditional Chinese medicine Trichosanthes kirilowii, which could lower the level of glycemic, so it is effective agents for the treatmen of diabetes in clinic. However, it was reported that 5-HMF may have a weak cytotoxic, mutagenic, carcinogenic and other toxic side. The aim of this study is to discover new hypoglycemic drugs with high activities. Based on the structure of 5-HMF, fourteen new compounds were synthesized via condensation, esterification, pro- tection and deprotection, whose structures were confirmed by 1H-NMR and MS. Eight compounds （ 1 - 7, 14 ） were detected in vitro for hypoglycemic activity by observing their effects on absorption rate of glucose,all of them showed certain activities at 10 Ixg .mL-1 concentration, among which compound 6 exhibited the strongest hypoglycemic activity to insulin with 87.45% absorption rate of glucose. The activity was much better than the parent compound 5-HMF. The structure-activity relationship of its derivatives as a novel of hypoglycemic drugs will be investigated further.

关 键 词：合成 5-羟甲基-2-呋喃甲醛衍生物 降血糖活性 

分 类 号：R914[医药卫生—药物化学]