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Polysubstituted benzene compound with biological activity, and preparation method and application thereof

A bioactive, benzene compound technology, applied in the field of multi-substituted benzene compounds and their preparation, can solve the problems of harsh reaction conditions, low specificity, poor selectivity, etc.

Active Publication Date: 2019-08-20
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The production and research of anti-tumor drugs in my country has made great progress, but the products are still far from meeting the growing needs of clinical practice, and many of them still rely on imports. Therefore, the market potential for the development and production of anti-tumor drugs is still huge
Traditional chemotherapeutic drugs have obvious clinical therapeutic effects, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious tumor multi-drug resistance, which limits clinical application. Looking for safe and effective anti-tumor drugs Drugs have always been the pursuit of the pharmaceutical industry
These methods often require harsh reaction conditions, expensive reagents or metal catalysts that are harmful to the environment, and have the disadvantages of cumbersome operation and low reaction regioselectivity.

Method used

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  • Polysubstituted benzene compound with biological activity, and preparation method and application thereof
  • Polysubstituted benzene compound with biological activity, and preparation method and application thereof
  • Polysubstituted benzene compound with biological activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Preparation of 2-methyl-3-(prop-2-yn-1-yloxy)-4H-pyran-4-one (compound V-1)

[0109] The synthetic route is as follows:

[0110]

[0111] Concrete synthetic steps are as follows:

[0112] 15g of compound VII-1 methyl maltol, 3 equivalents of potassium carbonate and 1.2 equivalents of propargyl bromide were added to 300 milliliters of acetonitrile, heated to 80 ° C for 12 hours; after the reaction, filter with a short silica gel column, reduce The solvent was removed by pressure evaporation, and 17.2 g of compound V-1 was obtained by column chromatography with a yield of 88%.

Embodiment 2

[0114] Preparation of 5,6-dihydroxy-7-methyl-1-phenyl-2,3-dihydro-1H-indene-4-carbaldehyde (compound 1-2)

[0115] The synthetic route is as follows:

[0116]

[0117] Concrete synthetic steps are as follows:

[0118] Add 0.25 mmol of compound V-1, 3.5 equivalents of p-methylstyrene and 1 ml of chlorobenzene into a Shrek tube, heat to 150°C for 13 hours under nitrogen protection, cool down to room temperature, spin dry, and pass through the column to obtain a yellow solid 50.1 mg, namely compound I-2, yield 71%.

Embodiment 3

[0120] Preparation of 1-(3-bromophenyl)-5,6-dihydroxy-7-methyl-2,3-dihydro-1H-indene-4-carbaldehyde (compound I-10)

[0121] The synthetic route is as follows:

[0122]

[0123] Concrete synthetic steps are as follows:

[0124] Add 0.25 mmol of compound V-1, 3.5 equivalents of m-bromostyrene and 1 ml of chlorobenzene into a Shrek tube, heat to 150°C for 13 hours under nitrogen protection, cool down to room temperature, spin dry, and pass through the column to obtain 45 mg of a yellow solid , namely compound I-10, the yield was 52%.

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PUM

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Abstract

The invention discloses a polysubstituted benzene compound with biological activity, and a preparation method and an application thereof. The compound provided by the invention has good biological activity, has the activity of inhibiting proliferation of tumor cells, can be used as a lead compound for research and development of a novel drug, and is used for preparation of antitumor drugs, such asdrugs for treating gastric cancer, drugs for treating ovarian cancer, drugs for treating lung cancer and drugs for treating prostate cancer. The synthetic method provided by the invention has the advantages of extensively-available raw materials, simple operation, simple and short route, mild reaction conditions, low cost and potential industrial value.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a multi-substituted benzene compound with biological activity and a preparation method and application thereof. Background technique [0002] Neoplastic disease, one of the leading causes of death in humans and other mammals, is characterized by cellular proliferation that is out of control of normal cellular proliferation. The production and research of anti-tumor drugs in my country has made great progress, but the products are still far from meeting the growing clinical needs, and many of them still rely on imports. Therefore, the market potential for the development and production of anti-tumor drugs is still huge. Traditional chemotherapeutic drugs have obvious clinical therapeutic effects, but their disadvantages are: low specificity and poor selectivity, leading to obvious toxic and side effects, and prone to serious tumor multi-drug resistance, which limits clinical app...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/57C07C205/44C07D309/22C07C47/575C07C255/56C07D333/22C07C69/94C07D333/78C07C49/84C07C323/22C07D307/46C07C49/83C07J1/00C07J9/00C07C69/76C07C43/205C07C43/23C07C43/178C07C39/17C07C65/24A61P35/00
CPCC07C47/57C07C205/44C07D309/22C07C47/575C07C255/56C07D333/22C07C69/94C07D333/78C07C49/84C07C323/22C07D307/46C07C49/83C07J1/0011C07J1/0059C07J9/00C07C69/76C07C43/2055C07C43/23C07C43/178C07C39/17C07C65/24A61P35/00C07C43/205C07D309/26C07C43/1783C07C43/1785C07C2602/08C07C2603/94C07F7/1804C07C43/115C07C323/18C07C37/01C07J75/00C07D309/20A61K31/11A61K31/351A61K31/381A61K31/566C07C45/60C07D307/42C07J5/0053A61K31/05A61K31/34
Inventor 祝诗发曹同祥王永东黄志鹏
Owner SOUTH CHINA UNIV OF TECH
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