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2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof, synthetic method and application of 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof

A technology of hydroxybenzoate and dimethoxybenzoate is applied in the fields of 2-phenyl-3,4-dihydroxybenzoate and its derivatives and synthesis to inhibit cell proliferation and reaction Mild conditions and easy post-processing results

Pending Publication Date: 2022-07-15
GUIZHOU MEDICAL UNIV
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Its related derivatives have not been reported in the literature

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  • 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof, synthetic method and application of 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof
  • 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof, synthetic method and application of 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof
  • 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof, synthetic method and application of 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy-benzoate and derivative thereof

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Effect test

Embodiment 1

[0126] Compound 1: Preparation of 2-bromo-6-(isoxazol-5-yl)phenyl-3,4-dihydroxybenzoate:

[0127] (1) Synthesis of 2-bromo-6-(5-isoxazolyl) phenol:

[0128] 1-(3-Bromo-2-hydroxyphenyl)ethanone (5 mmol) and DMF-DMA (7.5 mmol) were added to a 50 mL flask, an appropriate amount of Toluene was added to dissolve, the reaction mixture was heated to 90 °C, and stirred at 90 °C for 2 h , then cooled to room temperature, Ethanol (5 mL) and NH were added to the reaction mixture 2 OH.HCl (7.6 mmol), then the solution was heated to 78 °C and stirred for 1 h, and the compound 2-bromo-6-(5-isoxazolyl)phenol was extracted and isolated.

[0129] NMR spectral data: 1 H NMR (600MHz, MeOD): δ 8.44 (d, J=1.9Hz, 1H), 7.84 (dd, J=7.9, 1.6Hz, 1H), 7.59 (dd, J=7.9, 1.6Hz, 1H), 6.96(d,J=1.9Hz,1H),6.92(t,J=7.9Hz,1H).

[0130] (2) Synthesis of 2-bromo-6-(isoxazol-5-yl)phenyl-3,4-dimethoxybenzoate:

[0131] 3,4-Dimethoxybenzoic acid (5.2 mmol) was added to a 50 mL flask, dissolved with an appropriat...

Embodiment 2

[0137] Compound 2: Preparation of 2-(3-methylisoxazol-5-yl)phenyl-3,4-dihydroxybenzoate:

[0138] (1) Synthesis of 2-(3-methylisoxazol-5-yl)phenol:

[0139] 2'-hydroxyacetophenone (5 mmol), pyridine 7.5 mmol), acetic anhydride (7.5 mmol) were added to a 50 mL flask, an appropriate amount of DCM was added to dissolve, the reaction mixture was stirred at room temperature for 6 h, and the dichloromethane in the reaction system was spin-dried , pyridine (3 mL), DBU (10 mmol) were added, the reaction system was refluxed at 100 °C for 7 h, then cooled to room temperature, NH2OH.HCl (7.6 mmol) was added to the reaction mixture, then the solution was heated to 78 °C and stirred for 1 h, extracted The compound 2-(3-methylisoxazol-5-yl)phenol was isolated.

[0140] NMR spectral data: 1 H NMR (600MHz, MeOD): δ 7.78 (dd, J=7.8, 1.6Hz, 1H), 7.26 (ddd, J=8.3, 7.3, 1.7Hz, 1H), 6.97–6.91 (m, 2H), 6.77 (s,1H),2.32(s,3H).

[0141](2) Synthesis of 2-(3-methylisoxazol-5-yl)phenyl-3,4-dimethox...

Embodiment 3

[0147] Compound 3: Synthesis of 2-chloro-6-(isoxazol-5-yl)phenyl-3,4-dihydroxybenzoate:

[0148] According to the preparation method of compound 1, 1-(3-chloro-2-hydroxyphenyl)ethyl-1-one was used to replace 1-(3-bromo-2-hydroxyphenyl)ethanone, and other operations were the same. The product is a white solid.

[0149] NMR spectral data: 1 H NMR (600MHz, MeOD): δ8.37 (d, J=1.9Hz, 1H), 7.92 (dd, J=8.0, 1.5Hz, 1H), 7.66 (ddd, J=8.1, 4.3, 1.8Hz, 2H) ), 7.61(d, J=2.1Hz, 1H), 7.44(t, J=8.0Hz, 1H), 6.93(d, J=8.3Hz, 1H), 6.63(d, J=1.9Hz, 1H). 13 C NMR (151MHz, MeOD): δ165.5, 164.9, 153.2, 152.2, 146.7, 145.7, 132.9, 130.3, 128.7, 127.8, 124.9, 124.5, 120.5, 118.0, 116.4, 103.7

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Abstract

The invention belongs to the field of medicinal chemistry, and particularly relates to 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy benzoate and a derivative thereof as well as a synthesis method and application of the 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy benzoate. 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy benzoate is designed and synthesized, and research shows that SD-0 does not affect the intracellular total beta-catenin content, and meanwhile, beta-catenin / BCL9PPI is affected, so that beta-catenin nuclear transfer is reduced, and colorectal cancer cell proliferation caused by Wnt / beta-catenin abnormal expression is inhibited; a series of 2-(isoxazole-5-yl) phenyl-3, 4-dihydroxy benzoate derivatives are synthesized, and meanwhile, the synthetic route for preparing the compound is simple, the reaction condition is mild, and post-treatment is convenient.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a 2-(isoxazol-5-yl)phenyl-3,4-dihydroxybenzoate and a derivative thereof, as well as a synthesis method and application thereof. Background technique [0002] Colorectal cancer (CRC) is one of the high-incidence malignant tumors in human beings. The new cases each year account for about 11% of the diagnosed tumor patients, and its morbidity and mortality are the third and second among all cancers, respectively. The occurrence and development of colorectal tumors is a multi-factor, multi-gene, multi-stage and progressive evolution process, in which the abnormal activation of the Wnt canonical signal transduction pathway plays an important role in regulating its occurrence, development, invasion and metastasis. [0003] Wnt pathway refers to a complex cell signaling pathway composed of Wnt family genes and their products and the protein products of many other related ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08A61P35/00
CPCC07D261/08A61P35/00
Inventor 董永喜董莉刘明吉吴淑霞毛永清廖尚高何迅张吉泉周孟关焕玉徐国波杨小生
Owner GUIZHOU MEDICAL UNIV
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