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Shikonin carboxylic ester derivatives containing cinnamate-like skeleton and synthesis method and application thereof

A technology of shikonin carboxylic acid and cinnamic acid, which is applied in the direction of drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problems of poor water solubility, cytotoxicity and side effects, and achieve the effect of low toxicity and side effects and significant inhibition of activity

Inactive Publication Date: 2020-11-20
济宁市第一人民医院
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  • Summary
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AI Technical Summary

Problems solved by technology

However, Shicaoning has not been used as an antineoplastic drug on the market or entered into a clinical candidate drug so far. This is related to its own physical and chemical properties and toxic and side effects. It is mainly manifested in poor water solubility and has certain toxic and side effects on normal tissues and cells. its clinical application

Method used

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  • Shikonin carboxylic ester derivatives containing cinnamate-like skeleton and synthesis method and application thereof
  • Shikonin carboxylic ester derivatives containing cinnamate-like skeleton and synthesis method and application thereof
  • Shikonin carboxylic ester derivatives containing cinnamate-like skeleton and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0025] Example 1: Preparation of Shikonin Pyridine Cinnamate Derivatives of Formula I

[0026] Take 0.05mol different substituted pyridine formaldehyde (1a-1o) and 0.06mol malonic acid in a 50mL round bottom flask, add 30mL pyridine solution to dissolve and drop 5-6 drops of piperidine, heat to 80-90°C, reflux, The reaction was stirred for 24 hours. After the reaction is over, pour an appropriate amount of ice water, add concentrated hydrochloric acid dropwise under stirring conditions to adjust the pH to 2 to 3, a large amount of solid products are precipitated, add an appropriate amount of saturated sodium chloride solution and stir, after standing for 2 hours, use a Buchner funnel to The precipitated solid was vacuum filtered and washed three times with water. The resulting solid was recrystallized in absolute ethanol, filtered to obtain the crystalline product and dried in a vacuum oven to constant weight, and the obtained product was pyridine cinnamic acid.

[0027] Wei...

example 2

[0044] Example 2: Application of pyridine cinnamate shikonin ester derivatives of formula I

[0045] MCF-7, HeLa, MDA-MB-231, A549, and L02 human normal liver cell lines were used as detection strains, and MTT colorimetry was used as the detection method, and the tumors of the derivatives of pyridine cinnamate and shikonin esters of formula Ⅰ were detected in vitro. The study of cell inhibitory activity found that this kind of novel structure derivative has obvious tumor cell inhibitory activity in vitro. see attached results figure 1 , 2 , 3, 4, 5.

example 3

[0046] Example 3: Compound C8 significantly induces Hela cell apoptosis

[0047] Compound C8 acted on Hela cells at different concentrations (0, 2, 4, 8 μM), treated for 24 hours, collected cells, centrifuged, washed cells twice with PBS; resuspended cells with binding buffer in PI / FITC double staining kit, Add 5 μL FITC and 10 μL PI respectively, and stain for 15 minutes in the dark, and detect cell apoptosis by flow cytometry. see attached results Figure 6 . The derivatives of this novel structure can obviously promote the apoptosis of human cervical cancer cell Hela.

[0048] The shikonin pyridine cinnamate derivatives of the present invention can be prepared into antitumor drugs.

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Abstract

The invention discloses a shikonin carboxylic ester derivatives containing cinnamate-like skeleton and synthesis method and application thereof, belongs to the technical field of chemical pharmacy, and particularly relates to shikonin derivatives and application thereof in tumor inhibition. Corresponding pyridine cinnamic acid is connected with shikonin through a synthesis means to obtain corresponding ester derivatives, and in-vitro antitumor activity research shows that the pyridine cinnamic acid shikonin derivatives have very strong inhibitory activity on tumor cell strains.

Description

[0001] 1. Technical field [0002] The invention belongs to the technical field of chemical pharmacy, and in particular relates to the preparation of a pyridine cinnamate shikonin derivative and its application in tumor suppression. [0003] 2. Background technology [0004] In China, comfrey is a commonly used Chinese herbal medicine, and its medicinal ingredient, zicaoning, has broad-spectrum activities, such as sterilization, anti-inflammatory, anti-immune deficiency, and anti-tumor. Previous studies have shown that it has great potential as a lead in the study of functional molecules that inhibit tumor activity. However, Shicaoning has not been used as an antineoplastic drug on the market or entered into a clinical candidate drug so far. This is related to its own physical and chemical properties and toxic and side effects. It is mainly manifested in poor water solubility and has certain toxic and side effects on normal tissues and cells. its clinical application. [0005...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/55C07D213/61C07D213/64A61P35/00
CPCA61P35/00C07D213/55C07D213/61C07D213/64
Inventor 孙文学江沛赵世媛刘蒙蒙郭玉金杨永华王小明王长水林红燕王雪
Owner 济宁市第一人民医院
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