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Compound, preparation method of the compound, application of the compound and products using the compound

A compound and product technology, applied in medical preparations containing active ingredients, drug combinations, organic chemistry, etc., can solve problems such as unsatisfactory inhibitory effects of histone deacetylase inhibitors

Active Publication Date: 2021-03-12
QINGDAO UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0011] The third object of the present invention is to provide the application of the above-mentioned compound in inhibiting the activity of histone deacetylase; The application in the acetylation level of protein H4; the fifth object of the present invention is to provide the application of the above-mentioned compound in the preparation of products for the treatment of diseases caused by histone acetylation disorders; the sixth object of the present invention is to provide the above-mentioned compound Application in the preparation of products for the treatment of cancer to alleviate the technical problem of the unsatisfactory inhibitory effect of histone deacetylase inhibitors on solid tumors existing in the prior art

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  • Compound, preparation method of the compound, application of the compound and products using the compound
  • Compound, preparation method of the compound, application of the compound and products using the compound
  • Compound, preparation method of the compound, application of the compound and products using the compound

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preparation example Construction

[0053] The present invention also provides the preparation method of above-mentioned compound, comprises carrying out according to the reaction shown in following formula (i):

[0054]

[0055] Wherein, R1 is independently selected from one or more of the following groups: hydrogen, methyl, trifluoromethyl, fluorine, chlorine or bromine;

[0056] Preferably, after the reaction is completed, the steps of quenching, extraction, washing, drying and solvent removal are also included in sequence;

[0057] Preferably, the extracted extract is ethyl acetate, dichloromethane or ether.

[0058] Specifically, compound 2 is generated from compound 1 and bromoacetonitrile, compound 2 is reacted with acid anhydride and then esterified to generate compound 3, compound 3 is reacted with hydroxylamine hydrochloride in solvent A to obtain compound 4, and compound 4 is reacted with different substituted benzoyl chlorides Generate compound 5, compound 5 reacts with hydroxylamine hydrochlorid...

Embodiment 1

[0078] The preparation of embodiment 1 YF452B

[0079]

[0080] Compound 2 is generated from compound 1 and bromoacetonitrile, compound 2 is reacted with acid anhydride and then esterified to generate compound 3, compound 3 is reacted with hydroxylamine hydrochloride in solvent A to obtain compound 4, compound 4 is reacted with different substituted benzoyl chlorides to generate compound 5 , compound 5 reacts with hydroxylamine hydrochloride in solvent B to generate compound 6, and compound 6 reacts with methoxy to generate the target compound YF452B. After the reaction is completed, it is generally quenched with ice water and extracted with ethyl acetate, dichloromethane, ether, etc. Washing with water and saturated saline successively, drying, removing the solvent under reduced pressure at low temperature, and obtaining the final product through column chromatography, the yield varies from 30% to 70%.

[0081] The solvent A is dimethylformamide, dioxane, toluene, benzene ...

Embodiment 2

[0084] Example 2 Histone Deacetylase Inhibitor Enzyme Activity Experiment

[0085]In this example, the histone deacetylase enzyme activity screening kit is used. In the experiment, the compound to be identified was mixed with histone deacetylase activity (HeLa cell or MDA-MB231 cell lysate) and histone deacetylase colorimetric substrate (containing an acetylated lysine side chain ) were incubated together. If the substrate is deacetylated, it will be activated, and then a luminescent group will be generated under the action of lysine chromogen. The final luminescent groups were read and analyzed with a microplate reader.

[0086] The result is as Figure 2A with Figure 2B As shown, the experimental results show that YF452B, similar to SAHA, can inhibit the activity of histone deacetylase in a concentration gradient-dependent manner, and at the same concentration, the inhibitory effect of YF452B on the activity of histone deacetylase is significantly better than that of S...

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Abstract

The invention provides a compound, a preparation method of the compound, and application of the compound as well as a product applying the compound, and relates to the technical field of small-molecule compounds. The structural formula of the compound provided by the invention is shown in a formula (I). It is verified by experiments that the compound has relatively strong function of inhibiting the activity of histone deacetylase (HDAC). At the cellular level, YF452B can remarkably inhibit the growth and movement of breast cancer cells at relatively low concentration. It is also verified by in-vitro and in-vivo experimental research that the compound has the activity of resisting breast cancer growth, metastasis and recurrence. The product containing the compound provided by the invention also can achieve the effect of treating cancer, and the dosage of a small-molecule drug is less; the specifity is strong; the side effects on a body is small; drug tolerance is less liable to generate. In addition, the invention further provides the preparation method of the compound. The method is convenient to operate and wide in universality; the prepared compound is high in purity and good in quality, and can effectively inhibit the growth and metastasis of cancel cells.

Description

technical field [0001] The invention relates to the technical field of small molecule compounds, in particular to a compound, a preparation method of the compound, an application of the compound and a product using the compound. Background technique [0002] Breast cancer is a diseased tumor formed when malignant tumor cells originating from breast epithelial cells invade and destroy normal breast tissue. Breast cancer is a highly heterogeneous malignant tumor. According to genotype classification, it mainly includes: LuminalA, LuminalB, HER2 and TNBC type. Breast cancer is one of the most common malignant tumors in women, and it is a very heterogeneous tumor. According to the statistics of the World Health Organization (WHO), about 1.67 million women suffered from breast cancer in 2012. Its incidence rate ranks first among female cancers (accounting for 25%), and its lethality rate ranks second, second only to lung cancer. Breast cancer occurs all over the world, but its ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/06A61K31/4245A61P35/00A61P35/04
CPCA61P35/00A61P35/04C07D271/06
Inventor 单佩佩李培峰杨飞飞朱素杰
Owner QINGDAO UNIV
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