Bouchardatine, Bouchardatine derivative and preparation methods and applications of Bouchardatine and Bouchardatine derivative

A technology of derivatives and drugs, applied in the field of Bouchardatine, can solve the problems of anti-obesity and alleviating fatty liver application, etc., and achieve the effects of improving drugability, reducing fat formation, and alleviating fatty liver formation.

Active Publication Date: 2015-02-25
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Bouchardatine is isolated from Bouchardatia neurococca. Modern studies have shown that Bouchardatine has various biological activities such as anti-cancer, anti-virus, and anti-tuberculosis, but its application in anti-obesity and alleviating fatty liver has not been seen.

Method used

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  • Bouchardatine, Bouchardatine derivative and preparation methods and applications of Bouchardatine and Bouchardatine derivative
  • Bouchardatine, Bouchardatine derivative and preparation methods and applications of Bouchardatine and Bouchardatine derivative
  • Bouchardatine, Bouchardatine derivative and preparation methods and applications of Bouchardatine and Bouchardatine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of compound 1

[0054] Put 1.36g of anthranilamide into a 50mL single-necked bottle, add 10mL of triethyl orthopropionate, adjust the temperature to 155°C for 19h, and monitor the completion of the reaction by thin-layer chromatography. The reaction solution was cooled to room temperature, a small amount of white solid precipitated, and then placed in the refrigerator to precipitate a large amount of solid, filtered, washed with ethanol, spin-dried the mother liquor, dissolved impurities in it with ethanol, filtered again, combined the filter cake, and dried to obtain a total of 1.51g White needle-like solid 1.

[0055] Yield 89.5%; 1 H NMR (400MHz, CDCl 3 )δ11.39(s, 1H), 8.31(d, J=7.9Hz, 1H), 7.83-7.67(m, 2H), 7.48(t, J=7.4Hz, 1H), 2.85(q, J=7.5 Hz, 2H), 1.46(t, J=7.6Hz, 3H); ESI-MS m / z: 175.2[M+H] + .

[0056]

Embodiment 2

[0057] Embodiment 2: the synthesis of compound 2

[0058] Add 1.5g of Compound 1 to 90mL of acetic acid, then add 705mg of sodium acetate, heat to 60°C, and stir for a while until the reaction solution is clear. Dissolve 0.5mL bromine into 10mL acetic acid, drop it into the reaction solution with a constant pressure dropping funnel, the reaction solution turns from brown to white turbidity, react for about 10 hours, pour the reaction solution into water, and a large amount of white solid precipitates , suction filtered and washed with a large amount of water. Drying under an infrared lamp gave 1.93 g of white solid 2.

[0059] Yield 88.7%; 1 H NMR (400MHz, DMSO) δ12.49(s, 1H), 8.12(d, J=8.0Hz, 1H), 7.86(t, J=7.8Hz, 1H), 7.70(t, J=8Hz, 1H) , 7.56(d, J=8.0Hz, 1H), 5.10(m, 1H), 2.01(d, J=8.0Hz, 3H); ESI-MS m / z: 255.0[M+H] + , 253.0[M-H] - .

[0060]

Embodiment 3

[0061] Embodiment 3: the synthesis of compound 3

[0062] Add 14.87g of compound 2 into 450mL of ethanol, then add 20.2mL of phenylhydrazine, heat to reflux, and react overnight, and a large amount of light yellow solids are found to be suspended the next day. Stop the reaction, cool and stand, filter, wash with a small amount of ethanol, recrystallize with ethanol, and dry to obtain 12.4 g of light yellow cotton-like light solid 3.

[0063] Yield 76%; 1 H NMR (400MHz, DMSO) δ11.50(s, 1H), 9.88(s, 1H), 8.13(d, J=7.9Hz, 1H), 7.81(t, J=7.6Hz, 1H), 7.68(d ,J=8.1Hz,1H),7.60(d,J=7.8Hz,2H),7.49(t,J=7.5Hz,1H),7.28(t,J=7.9Hz,2H),6.89(t,J =7.3Hz,1H),2.35(s,3H);ESI-MS m / z:279.2[M+H] + , 277.2[M-H] - .

[0064]

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PUM

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Abstract

Disclosed are applications of Bouchardatine and Bouchardatine derivative in preparation of an anti-obesity and fatty liver-relieving drug. The structural fomulas of the Bouchardatine and the Bouchardatine derivative are shown in a pattern (I), to be specific, R is -(CH<2>)<n>R<1>, R<1>is substituted phenyl, heterocyclic radical or substituted amidogen, and n is equal to 0, 1, 2 or 3. By the use of the Bouchardatine and the Bouchardatine derivative, differentiation of pre-adipocyte 3T3-L1 is restrained so as to reduce lipid accumulation in adipocyte 3T3-L1; lipid accumulation, caused by sodium oleate, in hepatoma carcinoma cells is reduced, zooblast triglyceride level is lowered, and anti-obesity and fatty liver-relieving effect is achieved.

Description

technical field [0001] The present invention relates to the technical field of Bouchardatine, more specifically, relates to a kind of Bouchardatine and Bouchardatine derivatives and their preparation method and application. Background technique [0002] Obesity, as a type of metabolic disease, is closely related to the occurrence and development of many other metabolic diseases, such as type 2 diabetes, atherosclerosis, and hypertension. Studies have shown that the formation of obesity is due to the body's exogenous energy intake exceeds the body's energy consumption, and the excess energy is stored in the form of triglycerides, which mediates the process of body metabolic disorders. At present, the World Health Organization's judgment of obesity is based on the Body Mass Index (BMI), that is, BMI≥30kg / m 2 is defined as obesity. With the development of the global economy, obesity and its complications have become a worldwide public health problem that seriously affects hum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/517A61K31/5377A61P3/04A61P1/16C07D403/04
CPCA61K31/517A61K31/5377C07D403/04A61K9/08A61K9/107A61K9/20A61K9/48
Inventor 黄志纾叶冀明刘宏饶勇陈迎春高琳余宏古练权
Owner SUN YAT SEN UNIV
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