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Design, Synthesis and Anti-diabetic Activities of Thiazole-bearing Compounds as Novel Dipeptidyl Peptidase Ⅳ Inhibitors

Author: ZhanFuXu
Tutor: WangJianWu
School: Shandong University
Course: Organic Chemistry
Keywords: Thiazole Type 2 diabetes mellitus Dipeptidyl peptidase IV Inhibitors
CLC: TQ464.8
Type: Master's thesis
Year: 2010
Downloads: 195
Quote: 0
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Abstract


Type 2 diabetes is a disease caused due to metabolic disorders worldwide to become a major public health problem. World Health Organization statistics show that around the world each year there are nearly three million people died from diabetes. 2025, the world will have 333 million type 2 diabetes patients, representing 90-95% of the total number of patients with diabetes. In China, the total number of patients with type 2 diabetes over 40 million, and caused great concern in the field of medicine. In the search for new treatment options, the number of new drug targets has been developed, DPP-Ⅳ targets for drug research hotspot. DPP-IV inhibitors can inhibit the activity of vivo dipeptidyl peptidase Ⅳ protect intestinal insulin from degradation, improving abnormal glucose tolerance and increased insulin sensitivity. 2006 Merck antidiabetic therapy West column Ting (sitagliptin, trade name Januvia) successfully listed as the first DPP-Ⅳ inhibitors, followed by Novartis' vildagliptin (vildagliptin, trade name Galvus) in 2007 The year also received the approval of the European Union, the United States and other countries. Saxagliptin, developed by BMS companies listed in the United States in 2009, became the third listed inhibitor of DPP-Ⅳ type 2 diabetes drug. The success of clinical applications, and helped to trigger a new boom of the DPP-Ⅳ inhibitor research. In 2004, Merck also found that the DPP-Ⅳ inhibitor, a class of thiazolidine ring. This class of compounds has a simple structure and activity characteristics. They found two of this series of compounds, the treatment of type 2 diabetes in a very good potential drug, their structure is as follows: the paper work is for the pilot to the above two compounds, design and synthesis of a number of columns containing thiazole ring DPP-IV inhibitors, in order to find new potential treatment of type 2 diabetes drug. To explore the influence of the different groups of pharmaceutically active, respectively, from the R terminal and a thiazole ring end of this series of compounds the modification, a total synthesis of the target compound (49), and its structure after H NMR, 13C NMR, MS, IR, characterization. Test their hypoglycemic effect, mice oral glucose tolerance test results showed that nine of compounds have strong hypoglycemic effect six (23,31,35,41,43,49) and gliclazide quite , three (12,16,38) stronger than gliclazide, prospects in the treatment of diabetes. Careful analysis of the structure-activity relationship can be established, the results show that the the thiazole ring volume group, will lead to poor activity of the compound.

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