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Novel diphenylpropene derivative, preparation method thereof and pharmaceutical composition

A technology of diphenylpropylene and its derivatives, applied in the chemical synthesis and pharmaceutical fields, to achieve the effect of promoting neurogenesis activity, low cytotoxicity, and reducing cytotoxicity

Active Publication Date: 2018-07-13
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of unknown mechanism and lack of three-dimensional structure of the target, it is impossible to rationally design based on the structure

Method used

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  • Novel diphenylpropene derivative, preparation method thereof and pharmaceutical composition
  • Novel diphenylpropene derivative, preparation method thereof and pharmaceutical composition
  • Novel diphenylpropene derivative, preparation method thereof and pharmaceutical composition

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preparation example Construction

[0097] The present invention also provides a preparation method of a novel diphenylpropene derivative, which is used to prepare the compound with the general formula II or the general formula III or the general formula IV or the general formula V, specifically using Based on the ligand-based skeleton transition, combined with the structural design principles of crossing the blood-brain barrier, the chalcone skeleton is modified, and the carbonyl group is removed by a multi-step reaction, and a new diphenylpropylene structure is finally obtained. figure 1 A flow chart showing a method for preparing a novel diphenylpropene derivative according to an embodiment of the present invention, refer to figure 1 , the method includes:

[0098] Step 101, select chalcone.

[0099] The selected chalcone has any one of the four structural formulas of the following structural formula a-structural formula d.

[0100]

[0101] Step 102, performing hydrogenation reaction and dehydration rea...

Embodiment 1

[0115] Example 1: Preparation of 1-(4-aminophenyl)-3-(3,4-methylenedioxyphenyl)-E-propene (LSS-23c).

[0116]

[0117] Add p-nitroacetophenone (18.0mmol, 3.00g) and lithium hydroxide monohydrate (288.0mmol, 12.08g) to a 100mL round bottom flask, dissolve in anhydrous methanol (15mL), stir at room temperature for 1.0h, then add 3,4-Methylenedioxybenzaldehyde (18.0mmol, 2.70g), reacted at room temperature for 3.0h. After the reaction, the methanol was evaporated to dryness, poured into 30 mL of distilled water and stirred, and 10% dilute hydrochloric acid was added dropwise to adjust the pH of the solution to 3-4. A yellow solid was precipitated, which was filtered by suction and dried to obtain compound LSS-23a (5.31 g, yield 99.2%).

[0118] Compound LSS-23a (7.5mmol, 2.20g) and anhydrous nickel chloride (15.0mmol, 1.96g) were added to a 100mL round bottom flask, dissolved in anhydrous methanol (75mL) and protected by argon. Sodium borohydride (45.0mmol, 1.70g) was added u...

Embodiment 2

[0121] Example 2: Preparation of 1-(4-aminophenyl)-3-(3,4-methylenedioxyphenyl)propanol

[0122]

[0123] Add compound LSS-23a (10.0mmol, 2.97g) to a 100mL round bottom flask, dissolve it with dry tetrahydrofuran (20mL), protect with argon, then add sodium borohydride (5.0mmol, 0.19g), carbon powder (10mmol , 0.12g), stirred and reacted at room temperature for 0.5h, then added distilled water (2ml), after TLC detection, suction filtered after the reaction, concentrated under reduced pressure, extracted with ethyl acetate (20mL), separated the organic phase, concentrated by rotary evaporation, and passed through the column layer Analysis (100-200 mesh silica gel, mobile phase: V (petroleum ether): V (ethyl acetate) = 4:1), drying to obtain a solid compound LHP-25 (2.43 g, yield 85%).

[0124] HRMS(ESI)(M-H) - m / z 298.0274, calcd for C 16 h 12 NO 5 298.0271. (acetone-d 6 ,400MHz)δ:8.21(d,J=8.8Hz,2H),7.73(d,J=8.8Hz,2H),7.01(d,J=1.6Hz,1H),6.88(dd,J 1 =8Hz,J 2 =1.6Hz,1H)...

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Abstract

The invention provides a novel diphenylpropene derivative and a preparation method thereof, and a pharmaceutical composition. The novel diphenylpropene derivative is a compound with the following general formula I, or the novel diphenylpropene derivative is an acceptable salt formed by a compound with the general formula I and an inorganic acid or an organic acid, wherein B is E-1-allyl group or E-2-allyl group; R1 and R3 are methoxy groups and R2 is hydrogen, or R2 and R3 form a methylenedioxy group, and R1 is hydrogen; the general formula I specifically comprises a general formula II, a general formula III, a general formula IV and a general formula V. Based on the setting of a specific substituent R, the novel diphenylpropene derivative has the effect of promoting the activity of the body nerves and the low cytotoxicity.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and pharmacy, in particular to a novel diphenylpropene derivative, a preparation method of the novel diphenylpropene derivative and a pharmaceutical composition. Background technique [0002] With the development of society, the aging of the population is accelerating, and the incidence of Alzheimer's disease (AD) accounts for about 10% of the elderly around the age of 65, or more than 60 million people. Suffering from different kinds of dementia, accounting for about 47% of the elderly over the age of 85, has become the fourth killer after heart disease, tumor and stroke. Currently, more than 20% of the population over the age of 60 in Europe, Japan and the United States suffer from the disease. It is predicted that the number of dementia patients will increase by 50% by 2020, doubling the total number of patients. In recent years, the incidence of this disease in our country is also increasi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54C07D317/58C07C217/84C07C233/25C07D407/12C07D405/12C07C233/60C07C275/32C07C213/08C07C231/02C07C273/18A61K31/36A61K31/136A61K31/167A61K31/443A61K31/27A61K31/4025A61K31/17A61P25/28
CPCC07C217/84C07C233/25C07C233/60C07C275/32C07D317/54C07D317/58C07D405/12C07D407/12
Inventor 梁建华李红鹏庆宏刘斯斯马聪璇范炳芝张贺奡杨亮全贞贞
Owner BEIJING INSTITUTE OF TECHNOLOGYGY