[1]何世波,肖智心,刘 建,等.槲皮素-３-O-乙酸-(４-(３H-１,２-二硫杂环戊烯 -３-硫酮))-苯酯的合成[J].湖北工业大学学报,2024,39(4):37-40.
　HE Shibo,XIAO Zhixin,LIU Jian,et al.Synthesis of quercetin-3-O-acetic acid-(4-(3H-1,2-dithiacyclopentene-3-thione))-phenyl ester[J].,2024,39(4):37-40.
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槲皮素-３-O-乙酸-(４-(３H-１,２-二硫杂环戊烯 -３-硫酮))-苯酯的合成()
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《湖北工业大学学报》[ISSN:1003-4684/CN:42-1752/Z]

卷:
39
期数:
2024年第4期
页码:
37-40
栏目:
出版日期:
2024-08-28

文章信息/Info

Title:
Synthesis of quercetin-3-O-acetic acid-(4-(3H-1,2-dithiacyclopentene-3-thione))-phenyl ester
文章编号:
1003-4684(2024)04-0037-04
作者:
何世波; 肖智心; 刘 建; 刘明星
(湖北工业大学生物工程与食品学院,湖北 武汉 ４３００６８)
Author(s):
HE Shibo;  XIAO Zhixin;  LIU Jian;  LIU Mingxing
(School of Biological Engin. and Food, Hubei Univ. of Tech., Wuhan 430068, China)
关键词:
芦丁; 槲皮素; H２S供体
Keywords:
rutin;  quercetin;  H2S donor;  synthesis
分类号:
R914.4
文献标志码:
A
摘要:
以芦丁为起始原料，以5(4羟基苯基)3H1,2二硫杂环戊烯3硫酮作为H2S供体，合成一种具有治疗糖尿病且促进伤口愈合功能的药物槲皮素3O乙酸(4(3H1,2二硫杂环戊烯3硫酮))苯酯。整个工艺路线包括取代、水解、williamson醚化、水解和酯化等5步反应，总产率为6.4 %。各步产物经MS、1H NMR分析表征。该合成路线具有原料廉价易得、反应条件温和、操作简便的优点。
Abstract:
A drug quercetin -3 -O -acetic acid -(4 -(3H -1,2 -dithiacyclopentene -3 -thione)) -phenyl ester with the function of treating diabetes and promoting wound healing was synthesized by using rutin as the starting material and 5 -(4 -hydroxyphenyl) -3H -1, 2 -dithiacyclopentene -3 -thione as the H2S donor. The whole process route included a total of five reaction steps including substitution, hydrolysis, williamson etherification, hydrolysis, and esterification, with a total yield of 6.4 %. The products of each step were characterized by MS and 1H NMR analysis. The synthetic route has the advantages of cheap and easy availability of raw materials, mild reaction conditions and simple operation.

参考文献/References:

［1］WANG G,LI W,CHEN Q,et al. Hydrogen sulfide accelerates wound healing in diabetic rats [J ]. International Journal of Clinical and Experimental Pathology,2015,8(05):5097 -5104. [2 ]DAⅥES M J,D’ALESSIO D A,FRADKIN J,et al. Management of Hyperglycemia in type 2 diabetes,2018. a consensus report by the american diabetes association(ADA) and the european association for the study of diabetes(EASD) [J ]. Diabetes Care,2018,41(12):2669 -2701. [3 ]BENNETT W L,MARUTHUR N M,SINGH S,et al. Comparative effectiveness and safety of medications for type 2 diabetes: an update including new drugs and 2 -drug combinations [J ]. Annals of Internal Medicine,2011,154(09):602 -613. [4 ]SHI G J,LI Y,CAO Q H,et al. In vitro and in vivo evidence that quercetin protects against diabetes and its complications: a systematic review of the literature [J ]. Biomedicine &Pharmacotherapy,2019,109:1085 -1099. [5 ]WANG M J,CAI W J,ZHU Y C. Mechanisms of angiogenesis: role of hydrogen sulphide [J ]. Clinical and Experimental Pharmacology and Physiology,2010,37(07):764 -771. [6 ]VACEK T P,GILLESPIE W,TYAGI N,et al. Hydrogen sulfide protects against vascular remodeling from endothelial damage [J ]. Amino Acids,2010,39(05):1161 -1169. [７] 王忠雷,张小华,杨丽燕,等．拼合原理在降血糖新药研 发中的应用设想[J]．中国实验方剂学杂志,２０１３,１９ (０４):３５１-３５４． [８] CHEVEREAUG,BOLLENBACH T．SystematicdisＧ coveryofdruginteraction mechanisms[J]．Molecular SystemsBiology,２０１５,１１(０４):８０７．

备注/Memo

备注/Memo:
［收稿日期］ 20221028［基金项目］ 国家级大学生创新创业训练计划项目(202110500010)［第一作者］ 何世波(1997-)， 男， 安徽六安人， 湖北工业大学硕士研究生， 研究方向为新药研发。［通信作者］ 刘明星(1970-)， 男， 湖北武汉人， 工学博士， 湖北工业大学教授， 研究方向为新药研发。
更新日期/Last Update: 2024-08-23