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Aryl-substituted chalcones compound, its preparation method and its application

A technology of chalcones and compounds, applied in the field of aryl-substituted chalcones and their preparation, can solve the problem of low anti-tumor activity of chalcones and achieve high inhibitory activity

Active Publication Date: 2012-02-08
NEOPANORA BIO TECH ZHUHAI LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the antitumor activity of current chalcone compounds is still low. We hope that by introducing aryl groups into the chalcone skeleton, changing the spatial conformation, designing a "fusion-shaped" molecule, and making this type of The molecule presents a "V"-shaped spatial conformation, thus obtaining a class of chalcone compounds with simple synthesis and excellent anti-tumor activity

Method used

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  • Aryl-substituted chalcones compound, its preparation method and its application
  • Aryl-substituted chalcones compound, its preparation method and its application
  • Aryl-substituted chalcones compound, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 (E)-3-(4-methoxyphenyl)-1-(3'-fluoro-[1,1'-biphenyl]-3-yl)prop-2-ene-1- Ketone (compound 1) synthesis:

[0040] 4eq m-bromoacetophenone and 5.2eq of 3-fluorophenylboronic acid with dioxane and 2M K 2 CO 3 Aqueous 1:1 mixed solution as solvent, add 0.2eq PdCl 2 (dppf), microwave heating at 150°C for 15 minutes, extraction of the organic layer with ethyl acetate, separation by column chromatography to obtain the intermediate 1-(3'-fluoro-[1,1'-biphenyl]-3-yl)ethanone , 1eq of the intermediate and 1eq of 4-methoxybenzaldehyde were dissolved in ethanol, 3eq of KOH was added as a catalyst, stirred at room temperature for 20h, adjusted to pH 3 with 1N HCl, extracted with ethyl acetate, and the organic layer was separated by column chromatography to obtain the product (E)-3-(4-methoxyphenyl)-1-(3′-fluoro-[1,1′-biphenyl]-3-yl)prop-2-en-1-one, producing rate of 65%.

[0041] Product NMR analysis:

[0042] 1 H NMR (500MHz, CDCl 3)δ8.19 (t, J=1.7Hz, 1H), 8.00 (dd...

Embodiment 2

[0043] Example 2 (E)-3-(4-methoxyphenyl)-1-(4'-fluoro-[1,1'-biphenyl]-2-yl)prop-2-ene-1- Ketone (compound 3) synthesis:

[0044] Dissolve 4eq of o-bromoacetophenone and 4eq of 4-methoxybenzaldehyde in ethanol, add 12eq of KOH as a catalyst, stir at room temperature for 20h, adjust the pH to 3 with 1N HCl, extract with ethyl acetate, and separate the organic layer by column chromatography Obtained intermediate (E)-3-(4-methoxyphenyl)-1-(2-bromophenyl)prop-2-en-1-one, 1 eq of intermediate and 1.3 eq of 4-fluorophenylboronic acid with dioxane and 2M K 2 CO 3 Aqueous solution 1:1 mixed solution as solvent, add 0.05eq PdCl 2 (dppf), microwave heating at 150°C for 15 minutes, extraction of the organic layer with ethyl acetate, separation by column chromatography to obtain the product (E)-3-(4-methoxyphenyl)-1-(4'-fluoro-[1 , 1'-biphenyl]-2-yl)prop-2-en-1-one, yield 76%.

[0045] Product NMR analysis:

[0046] 1 H NMR (500MHz, CDCl 3 )δ7.61(dd, J=7.6, 1.4Hz, 1H), 7.54(td, J=7...

Embodiment 3

[0047] Example 3 (E)-3-(4-methoxyphenyl)-1-(3'-fluoro-[1,1'-biphenyl]-2-yl)prop-2-ene-1- Ketone (compound 11) synthesis:

[0048] 4.8eq o-bromophenylboronic acid and 4eq of 3-bromofluorobenzene with dioxane and 2M K 2 CO 3 Aqueous 1:1 mixed solution as solvent, add 0.2eq PdCl 2 (dppf), microwave heating at 150°C for 15 minutes, extraction of the organic layer with ethyl acetate, separation by column chromatography to obtain the intermediate 1-(3'-fluoro-[1,1'-biphenyl]-2-yl)ethanone , 1eq of the intermediate and 1eq of 4-methoxybenzaldehyde were dissolved in ethanol, 3eq of KOH was added as a catalyst, stirred at room temperature for 20h, adjusted to pH 3 with 1N HCl, extracted with ethyl acetate, and the organic layer was separated by column chromatography to obtain the product (E)-3-(4-methoxyphenyl)-1-(3′-fluoro-[1,1′-biphenyl]-2-yl)prop-2-en-1-one, producing rate of 72%.

[0049] Product NMR analysis:

[0050] 1 H NMR (400MHz, CDCl 3 )δ8.17(t, J=1.7Hz, 1H), 8.01-7....

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Abstract

The invention discloses an aryl-substituted chalcones compound, a preparation method and an application. The aryl-substituted chalcones compound has a structure shown as a formula(I) or a formula(II), wherein, R1, R2, R3, R4, R5 are aromatic groups or aromatic groups with a substituent, the aromatic groups are phenyl, furan, thienyl, pyridyl, pyrimidyl, thiazolyl or pyrrolyl, the substituent is one or more selected from hydroxyl, methoxyl, ethoxyl, methyl, ethyl, trifluoromethyl, halogen, amino, methylamino or dimethylamino; R3 is selected from hydrogen, amino or-NHCOCH3. The aryl-substituted chalcones compound introduces the aromatic groups based on a phenyl skeleton to form a structure with steric hindrance, the molecule presents a V-shaped spatial conformation, compared with the current chalcone compounds, and the aryl-substituted chalcones compound has higher inhibitory activity to cancer cells and can be used for preparing the antitumor drugs.

Description

technical field [0001] The invention belongs to the field of drug design and synthesis, and specifically relates to an aryl-substituted chalcone compound and a preparation method and application thereof. Background technique [0002] Chalcones widely exist in nature, and their basic skeleton structure is 1,3-diphenylpropenone. Current studies have found that the introduction of various substituents on the basic skeleton structure can enable chalcones to exhibit new physiological and pharmaceutical activities. The existing activities of chalcones include anti-inflammatory activity, anti-angioproliferative activity, antimicrobial activity, antibacterial activity, optical recording material, antidepressant, pesticide, antitumor, etc. For example, Chinese patent CN200710037570.8 discloses a type of chalcone compounds that have the effect of inhibiting tumor or inhibiting excessive cell proliferation. [0003] The biaryl structure is a pharmacophore existing in natural products...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/68C07C225/22C07C221/00C07D213/61A61K31/4418A61K31/136A61K31/12A61P35/00
Inventor 卜宪章左应林杜军温格斯周斌华商娜娜
Owner NEOPANORA BIO TECH ZHUHAI LTD
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