阅读说明：本技术 一种羟基取代的二苯甲酮类化合物及其制备方法和应用 (Hydroxyl-substituted benzophenone compound and preparation method and application thereof ) 是由 周北斗 黄堡城 于 2019-05-06 设计创作，主要内容包括：一种羟基取代的二苯甲酮类化合物,为(4-羟基苯基)(3,5-二甲基-2-羟基苯基)甲酮,其结构如下式所示：<Image he="261" wi="509" file="DDA0002050042420000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(4-羟基苯基)(3,5-二甲基-2-羟基苯基)甲酮为一种新的二苯甲酮类化合物,具有明显的抗肿瘤活性和抑制酪氨酸酶的活性,可用于制备抗肿瘤药物和酪氨酸酶代谢调节药物、保健品、食品、化妆品。本发明提供的(4-羟基苯基)(3,5-二甲基-2-羟基苯基)甲酮制备方法操作简单,反应条件温和,产率高,可用于(4-羟基苯基)(3,5-二甲基-2-羟基苯基)甲酮的大量制备。(A hydroxyl-substituted benzophenone compound is (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and the structure of the compound is shown as the following formula: the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone is a new benzophenone compound, has obvious antitumor activity and tyrosinase inhibiting activity, and can be used for preparing antitumor drugs and tyrosinase metabolism regulating drugs, health products, foods and cosmetics. The preparation method operation of the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone provided by the inventionSimple, mild reaction condition and high yield, and can be used for the mass preparation of (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone.)

1. A hydroxyl-substituted benzophenone compound is characterized in that the compound is (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and the structure of the compound is shown as the chemical formula (I):

2. a process for preparing the compound of claim 1, which comprises reacting 4-hydroxybenzoic acid, 2, 4-dimethylphenol, phosphorus pentoxide and methanesulfonic acid.

3. The method according to claim 2, wherein the molar ratio of 4-hydroxybenzoic acid to 2, 4-dimethylphenol is 1: 1.

4. The method of claim 2, comprising the steps of:

1) dissolving phosphorus pentoxide in methanesulfonic acid to prepare a first mixed solution;

2) 4-hydroxybenzoic acid and 2, 4-dimethylphenol are added to the first mixed solution to carry out a dehydration reaction to produce (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone.

5. The method of claim 4, further comprising the steps of:

and (3) carrying out precipitation, suction filtration and column chromatography separation on the solution containing the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone after the reaction in the step 2) is finished to obtain the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone with high purity.

6. The method according to claim 4, wherein the dissolving temperature in the step 1) is controlled to be 105 to 115 ℃.

7. The preparation method according to claim 4, wherein in the step 2), the reaction temperature is controlled to be 80-90 ℃ and the reaction time is controlled to be 2.5-3.5 h.

8. Use of a hydroxy-substituted benzophenone compound of claim 1 to inhibit tyrosinase activity.

9. The use of the hydroxy-substituted benzophenone compound of claim 1 in antineoplastic agents.

10. The use of the hydroxy-substituted benzophenones as claimed in claim 1 for drugs, health products, foods and cosmetics for regulating tyrosinase metabolism.

Technical Field

The invention relates to the field of biochemical medicine, in particular to a hydroxyl-substituted benzophenone compound and a preparation method and application thereof.

Background

The benzophenone compound can be synthesized and can also be separated from some plants. The compounds have a plurality of important biological activities, such as antitumor activity, neuroprotection, fatty acid synthetase inhibition and the like. These different biological activities are determined by the different substituents on the two phenyl rings. The biological activity of the benzophenone compound is determined by different substituents on two benzene rings, and the biological activity can be influenced by changing one or more substituents.

Disclosure of Invention

Therefore, the invention aims to provide a hydroxyl substituted benzophenone compound with certain physiological and pharmacological activity.

In order to realize the purpose of the invention, the invention adopts the following technical scheme:

a hydroxyl-substituted benzophenone compound is (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and the structure of the compound is shown in the chemical formula (I):

further, the method comprises a process of reacting 4-hydroxybenzoic acid, 2, 4-dimethylphenol, phosphorus pentoxide and methanesulfonic acid.

Further, the molar ratio of 4-hydroxybenzoic acid to 2, 4-dimethylphenol was 1: 1.

Further, the method comprises the following steps:

1) dissolving phosphorus pentoxide in methanesulfonic acid to prepare a first mixed solution;

2) adding 4-hydroxybenzoic acid and 2, 4-dimethylphenol into the first mixed solution, and performing dehydration reaction to generate (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone;

further, the solution containing (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone after the reaction in 2) is precipitated, filtered by suction, and separated by column chromatography to obtain the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone with high purity.

Further, in the step 1), the dissolving temperature is controlled to be 105-115 ℃.

Further, in the step 2), the reaction temperature is controlled to be 80-90 ℃, and the reaction time is controlled to be 2.5-3.5 h.

In the preparation, the control of the temperature is crucial. Too high a temperature carbonizes the raw material to lower the yield, while too low a temperature affects the reaction rate.

The invention also provides application of the compound shown in the formula I in inhibiting tyrosinase activity.

The invention also provides application of the compound shown in the formula I in antitumor drugs.

The invention also provides application of the compound shown in the formula I in the aspects of tyrosinase metabolism regulation medicines, health-care products, foods and cosmetics.

The compound (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone shown in the formula I is a novel benzophenone compound, has obvious antitumor activity and tyrosinase inhibition activity, and can be used for preparing antitumor drugs and tyrosinase metabolism regulation drugs, health care products, foods and cosmetics. The preparation method of the compound shown in the formula I has the advantages of simple operation, mild reaction conditions and high yield, and can be used for large-scale preparation of the compound shown in the formula I.

Detailed Description

In order to explain technical contents, structural features, and objects and effects of the technical means in detail, the following detailed description is given with reference to specific embodiments.

The invention adopts the following technical scheme:

a hydroxyl-substituted benzophenone compound is (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and the structure of the compound is shown in the chemical formula (I):

further, the method comprises a process of reacting 4-hydroxybenzoic acid, 2, 4-dimethylphenol, phosphorus pentoxide and methanesulfonic acid.

Further, the molar ratio of 4-hydroxybenzoic acid to 2, 4-dimethylphenol was 1: 1.

Further, the method comprises the following steps:

1) dissolving phosphorus pentoxide in methanesulfonic acid to prepare a first mixed solution;

2) adding 4-hydroxybenzoic acid and 2, 4-dimethylphenol into the first mixed solution, and performing dehydration reaction to generate (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone;

further, the solution containing (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone after the reaction in 2) is precipitated, filtered by suction, and separated by column chromatography to obtain the (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone with high purity.

Further, in the step 1), the dissolving temperature is controlled to be 105-115 ℃.

Further, in the step 2), the reaction temperature is controlled to be 80-90 ℃, and the reaction time is controlled to be 2.5-3.5 h.

In the preparation, the control of the temperature is crucial. Too high a temperature carbonizes the raw material to lower the yield, while too low a temperature affects the reaction rate.

The invention also provides application of the compound shown in the formula I in inhibiting tyrosinase activity.

The invention also provides application of the compound shown in the formula I in antitumor drugs.

The invention also provides application of the compound shown in the formula I in the aspects of tyrosinase metabolism regulation medicines, health-care products, foods and cosmetics.

The compound (4-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone shown in the formula I is a novel benzophenone compound, has obvious antitumor activity and tyrosinase inhibition activity, and can be used for preparing antitumor drugs and tyrosinase metabolism regulation drugs, health care products, foods and cosmetics. The preparation method of the compound shown in the formula I has the advantages of simple operation, mild reaction conditions and high yield, and can be used for large-scale preparation of the compound shown in the formula I.

For a further understanding of the present invention, reference will now be made in detail to the following examples.