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The Synthesis of Amino Acids Derivatives for the Treatment of T2DM

Author: YuZhiBing
Tutor: ChenXingJuan
School: Harbin Engineering University
Course: Applied Chemistry
Keywords: Type 2 diabetes mellitus PPAR Insulin sensitizers Amino acid derivatives Organic Synthesis
CLC: R914
Type: Master's thesis
Year: 2007
Downloads: 156
Quote: 1
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Abstract


Diabetes is a absolute or relative lack of endocrine and metabolic disease caused by insulin in the body, with the improvement of people's living standards, its incidence is increasing year by year, and are getting younger and younger, it has become the major diseases of serious harm to human health one. People are actively seeking a cure for diabetes drug, in order to overcome the problems of the world, but in recent years, many of the treatment of diabetes new drugs have varying degrees of toxicity. Looking for efficiency and low toxicity nor side effects of new drugs, is still arduous task of chemistry and pharmacy workers. Currently, the treatment of type 2 diabetes drug research direction is the development of new PPARγ partial agonists, PPARα / γ dual effect agonist. Herein, the synthesis of new compounds having anti-diabetic efficacy, respectively having one or more active in the activity of PPARα, PPARγ, and some activity of the compounds at the same concentration to be higher than the pioglitazone, such insulin sensitizers both can improve the body's sensitivity to insulin, but also can reduce white fat deposition by regulating the content of free fatty acids and triglycerides, is expected to reduce cardiovascular complications and did not induce obesity. MCC-555, JTT-501, KRP-297, BMS-298585, a lead compound, its structure transformation, design of the seven amino acid derivatives, a preparation of such compounds, synthetic routes explored by experiment, seven amino acid derivatives were synthesized, respectively, N-[(4 - methoxy-phenyl) carbonyl]-N-[(4 - (2 - (9 - carbazol-yl) ethoxy) phenyl) methyl ] glycine (LTD-1), N-[4 - [2 - [N-methyl-N-(2 - benzo ah thiazolyl) amino] ethoxy] phenyl] methyl]-N-[(4 - methoxy-phenyl) carbonyl] glycine (LTD-2), N-[(4 - methoxy-phenyl) carbonyl]-N-[2 - [6 - (2 - fluorobenzyloxy) naphthyl] methyl] glycine (LTD-3), N-[(4 - methoxy phenyl) carbonyl yl]-N-[2 - [6 - (4 - fluoro-benzyloxy) naphthyl] methyl] glycine (LTD-4), N-[(4 - methoxy-phenyl) carbonyl yl]-N-[[4 - [(1 - methyl - benzimidazol-2 - yl) methoxy] phenyl] methyl] glycine (LTD-5 ), N-[[4 - [3 - [(4 - phenoxy) phenoxy] propoxy] phenyl] methyl]-N-[(4 - methoxyphenyl) carbonyl] glycine (LTD -6), N-[[4 - [2 - [(4 - phenoxy) phenoxy] ethoxy] phenyl] methyl]-N-[(4 - methoxyphenyl) carbonyl] glycine (LTD-7), its structure is confirmed by ~ 1HNMR. The biological activity screening that can activate PPAR receptors the LTD1 LTD4, LTD6, and LTD7 improve insulin resistance and lipid-lowering activity of drugs can be used as a good candidate.

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