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Medicine for preventing and treating diabetes and diabetic nephropathy, and synthetic method and application thereof

A kind of technology of diabetic nephropathy, synthesis method

Active Publication Date: 2016-12-21
XIAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] With the deepening of research, the original method of extracting compounds from natural products can no longer meet the needs of activity and structure-activity relationship research. It is necessary to study new synthetic methods. At the same time, more in-depth research on caffeic acid-phenylalanine It is also very meaningful to study the biological activity of acid amide compounds and their analogs, and to provide them with new applications, especially in pharmaceutical applications.

Method used

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  • Medicine for preventing and treating diabetes and diabetic nephropathy, and synthetic method and application thereof
  • Medicine for preventing and treating diabetes and diabetic nephropathy, and synthetic method and application thereof
  • Medicine for preventing and treating diabetes and diabetic nephropathy, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0047] The synthesis of example 1 caffeic acid-phenylalanine amide compound (CP1 for short, as shown in formula II)

[0048]

[0049] 1) Weigh 90mg (0.5mmol) of caffeic acid and add it to a 10mL round-bottomed flask, add 5mL of trichloroethane dropwise to the round-bottomed flask to dissolve the caffeic acid;

[0050] 2) Add 208 μL (about 1.5 mmol) of triethylamine to the round bottom flask, and stir for 10 min in an ice-water bath to bring the temperature of the system to 0°C;

[0051] 3) Add 143 mg (0.75 mmol) of EDCI (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) and DMAP ( 4-Dimethylaminopyridine) 91.5 mg (0.75 mmol), after 20 min, add L-phenylalanine hydrochloride 101 mg (0.5 mmol) to the round bottom flask, the temperature rose to 40 ° C, and continued to stir under the condition of Respond for 24 hours;

[0052] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evaporation, -0.08MPa, 45°C), and 20 mL of ethyl acetate was added ...

example 2

[0053] The synthesis of example 2 ferulic acid-phenylalanine isopropyl ester (CP2 for short, as shown in formula III)

[0054]

[0055] 1) Weigh 97 mg (0.5 mmol) of ferulic acid and add it to a 10 mL round-bottomed flask, add 6 mL of DCM (dichloromethane) dropwise to the round-bottomed flask to dissolve the ferulic acid;

[0056] 2) Add 205 μL (about 1.5 mmol) of diisopropylamine to the round bottom flask, and stir for 15 minutes in an ice-water bath to make the temperature of the system reach 0°C;

[0057] 3) Add NMM (N-methylmorpholine) 101mg (1mmol) and IBCF (isobutyl chloroformate) 135mg (1mmol) to the round-bottomed flask under ice-water bath and stirring conditions, and pour into the round-bottomed flask after 40min Then add 101 mg (1 mmol) of L-phenylalanine isopropyl ester hydrochloride, raise the temperature to 80°C, and continue to react under stirring conditions for 18 hours;

[0058] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evap...

example 3

[0059] Example 3 Synthesis of 3-acetyl-caffeic acid-β-naphthylalanine benzyl ester (CP3 for short, shown in formula IV)

[0060]

[0061] 1) Weigh 111mg (0.5mmol) of the raw material 3-acetyl-caffeic acid (structural formula is as follows) into a 10mL round-bottomed flask, and add 5mL of toluene dropwise into the round-bottomed flask to dissolve the raw material;

[0062]

[0063] 2) Add 70 μL (about 0.5 mmol) of triethylamine to the round-bottomed flask, and stir for 20 minutes in an ice-water bath to make the temperature of the system reach 0°C;

[0064] 3) Add EDCI 95mg (0.5mmol) and HOBt67.3mg (0.5mmol) to the round bottom flask under ice-water bath and stirring conditions, and then add β-L-naphthylalanine benzyl ester to the round bottom flask after 30min 183mg (0.6mmol), the temperature was raised to 60°C, and the reaction was continued for 48 hours under stirring;

[0065] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evaporation, -0.0...

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Abstract

The invention discloses a medicine for preventing and treating diabetes and diabetic nephropathy, and a synthetic method and an application thereof. The medicine is a caffeic acid-phenylalanine derivative, and has a structure represented by formula I; and in the formula I, R<1> and R<2> are H, OH, OCH3, OCOCH3, 3-methylbutyl-2-vinyl group or an isopentenyl group, R<3> is H, CH3, Bn, OCH3, OCOCH3, BnCH2, i-Pr, t-Bu or an adamantyl group, and n is 0 or 1. An STZ induced rat diabetic model shows that the derivative substantially reduces the blood sugar of diabetic model rats, and has a certain protection effect on diabetic nephropathy model mice, so the blood sugar reducing effect and the kidney protecting effect of the derivative are confirmed, and the derivative can be used to prepare diabetes and diabetic nephropathy correlated medicines.

Description

technical field [0001] The invention belongs to the field of pharmacy and relates to the application of caffeic acid-phenylalanine derivatives in hypoglycemic and renal protection, in particular to the use of the derivatives in the preparation of anti-diabetic and its complications and other related medicines. Background technique [0002] Caffeoyl-N-phenylalanine amide compound (Caffeoyl-N-phenylalanine), chemical name is (trans)-3-(3,4-dihydroxyphenyl)acrylic acid-L-phenylalanine, widely present in various In coffee beans, such as small-grain coffee, medium-fruit coffee, robusta coffee, etc., this compound was first isolated and identified from the Himalayan hoofed fern (Athyrium filix-femina) by the research group of Klaus Peter Adam in 1955. Subsequent studies have found that the compound is also widely present in other plants. [0003] Similar to the caffeic acid phenethyl ester compound in propolis, the caffeic acid-phenylalanine amide compound also has a very wide ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C235/34A61K31/198A61K31/216A61P3/10A61P13/12
CPCC07C231/02C07C235/34
Inventor 陈福欣龚频侯彬彬王兰文和马逢乐周安宁
Owner XIAN UNIV OF SCI & TECH
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