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A kind of phenylpropionate derivative and its preparation method and application

A technology of phenylpropionate and derivatives, which is applied in the field of related medicines, can solve the problems of less attention on lipid-lowering effect, achieve the effects of improving lipid metabolism, optimizing synthesis route and process parameter conditions, and increasing yield

Active Publication Date: 2021-02-26
XIAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The research on the existing hypoglycemic drugs such as sulfonylureas, thiazolidinediones, α-glucosidase inhibitors, DPP-IV inhibitors, and SGLT2 inhibitors mainly focuses on the hypoglycemic effect and the lipid-lowering effect At present, there is an urgent need to carry out the research and development of new diabetes therapeutic drugs that have therapeutic effects on diabetic complications and obese diabetes.

Method used

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  • A kind of phenylpropionate derivative and its preparation method and application
  • A kind of phenylpropionate derivative and its preparation method and application
  • A kind of phenylpropionate derivative and its preparation method and application

Examples

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example 1 2

[0050] The synthesis of example 1 dihydrocaffeic acid-2-naphthyl methyl ester (PN1 for short, as shown in formula II)

[0051]

[0052] 1) Weigh 1.10mmol of dihydrocaffeic acid, dissolve in 1.5mL DMSO, add 1.32mmol of Na 2 CO 3 After stirring at room temperature for 0.5 h, 1.10 mmol of potassium iodide and 1.20 mmol of 2-(chloromethyl)naphthalene were added in sequence. The reaction mixture was stirred at 60 °C for 6 h (end of reaction by TLC).

[0053] 2) After the reaction was completed, cool to room temperature, add 5 mL of saturated sodium chloride solution and 5 mL of ethyl acetate, mix well and let stand to separate layers; the aqueous phase was extracted twice with ethyl acetate (3 mL×2 times), and the organic phase was combined, Then washed with saturated copper sulfate solution (3mL×4 times), and saturated sodium chloride solution (2mL×2 times), dried over anhydrous sodium sulfate, and then rotary evaporated (-0.08MPa, 45°C) to remove the solvent to obtain solid ...

example 2

[0055] The synthesis of example 2 p-hydroxyphenylpropionic acid-1-naphthylmethyl ester (PN for short, as shown in formula III)

[0056]

[0057] 1) Weigh 1.10mmol of p-hydroxyphenylpropionic acid, dissolve in 1.5mL of acetone, add 2.2mmol of NaHCO 3 After stirring at room temperature for 1 h, 2.2 mmol of lithium iodide and 2.2 mmol of 1-(bromomethyl)naphthalene were sequentially added. The reaction mixture was stirred at 40 °C for 12 h (end of reaction by TLC).

[0058] 2) Cool to room temperature after the reaction, add 10mL of saturated sodium chloride solution and 5mL of ethyl acetate, mix well and let stand to separate layers; extract the aqueous phase twice with ethyl acetate (3mL×2 times), combine the organic phases, Wash with saturated sodium chloride solution (2 mL×2 times), dry over anhydrous sodium sulfate, and then remove the solvent by rotary evaporation (-0.08 MPa, 45° C.) to obtain a solid crude product.

[0059] 3) The crude product is purified by column ch...

example 3 2

[0060] The synthesis of example 3 dihydrocaffeic acid-1-naphthalene-(5-isopropyl)-methyl ester (PN for short, as shown in formula IV)

[0061]

[0062] 1) Weigh 1.10mmol of dihydrocaffeic acid, dissolve in 1.5mL DMF, add 3.3mmol of KHCO 3 After stirring at room temperature for 1 h, 3.3 mmol of sodium iodide and 1.20 mmol of 1-(chloromethyl)-(5-isopropyl)-naphthalene were added sequentially. The reaction mixture was stirred at 80 °C for 3 h (end of reaction by TLC).

[0063] 2) After the reaction was completed, cool to room temperature, add 5 mL of saturated sodium chloride solution and 5 mL of ethyl acetate, mix well and let stand to separate layers; the aqueous phase was extracted twice with ethyl acetate (3 mL×2 times), and the organic phase was combined, Then washed with saturated copper sulfate solution (4mL×4 times), and saturated sodium chloride solution (2mL×2 times), dried over anhydrous sodium sulfate, and then rotary evaporated (-0.08MPa, 45°C) to remove the solv...

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Abstract

The invention discloses a phenylpropionate derivative and its preparation method and application. The structure of the phenylpropionate derivative is shown in formula I: wherein, R 1 , R 2 H, OH, OCH 3 , isopentenyl, 3-methylbut-2-enyl, alkyl; R 3 for H, CH 3 , i-Pr, t-Bu, CF 3 or OCH 3 . The rat diabetes model induced by OGTT and STZ of normal mice shows that the derivative has significant hypoglycemic activity, and can reduce the blood sugar of diabetic model rats in a dose-dependent manner, and has a certain effect on hyperlipidemia diabetic mice The protective effect has confirmed the hypoglycemic and lipid-lowering effects of the derivative, and can be used to prepare related drugs for diabetes, especially obese diabetes and adjuvant treatment of diabetic complications.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a phenylpropionate derivative and its application in hypoglycemic and renal protection, in particular to the application of the derivative in the preparation of anti-diabetes and its complications and other related drugs. Background technique [0002] Diabetes is a chronic disease caused by disorders of the endocrine system. It is estimated that the number of people suffering from diabetes worldwide will increase from 285 million in 2013 to 566 million by 2030. Diabetes has a long duration of action and is characterized by high blood sugar, which can easily cause damage to other organs such as eyes, kidneys, blood vessels, and heart. It has the phenomenon of "three highs and three lows" with high prevalence rate, high mortality rate, high disability rate, low awareness rate, low treatment rate and low control rate. Diabetes is divided into type 1 diabetes and type 2 diabetes. Type 1 is c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C69/734C07C67/11C07C67/56A61P3/10A61P3/08A61P3/06
CPCC07C67/11C07C67/56C07C69/732C07C69/734
Inventor 陈福欣侯彬彬龚频文和郑超李刚周安宁
Owner XIAN UNIV OF SCI & TECH
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