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Chromone skeleton-containing polycyclic compound as well as preparation method and application thereof

A technology for polycyclic compounds and compounds, applied in the field of preparation of polycyclic compounds containing chromone skeleton, can solve the problems of unreported synthetic methods and high price

Active Publication Date: 2020-10-02
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0013] However, the current method for preparing chromones using norbornene has the following disadvantages: Although there have been a series of reports that norbornene, as a C2 unit, participates in the palladium-catalyzed [2+2+2] reaction for the chromone-containing skeleton Construction of polycyclic compounds, but the reaction raw material is iodobenzene with higher price
At the same time, the [2+2+1] reaction involving norbornene as a C2 unit has not been reported for the synthesis of chromone-containing polycyclic compounds.

Method used

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  • Chromone skeleton-containing polycyclic compound as well as preparation method and application thereof
  • Chromone skeleton-containing polycyclic compound as well as preparation method and application thereof
  • Chromone skeleton-containing polycyclic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] 3-iodochromone (0.2mmol), benzyl bromide (0.22mmol), norbornene (0.8mmol, 75.3mg), palladium acetate (0.02mmol, 4.5mg), three (2-methylphenyl) phosphorus (0.04mmol, 12.2mg), potassium phosphate (0.4mmol, 84.9mg), mesitylene (1.2mL) and acetonitrile (0.8mL) were added to a 4mL reaction flask under nitrogen at 100°C, and reacted at 100°C for 24h, After the reaction is finished, cool to room temperature, and the resulting reaction solution is subjected to column chromatography (the eluent is obtained by mixing ethyl acetate and petroleum ether according to a volume ratio of 50:1–20:1), and the obtained reaction solution is obtained by column chromatography. The solvent was removed from the solution to obtain 23 mg of a yellow solid (4a), and 20 mg of a light yellow solid mixture of 4a and 4a', with an overall yield of 65%. The diastereoselectivity was determined to be 86:14, and the melting point was 158.0-159.3°C.

[0058] The above-mentioned yellow solid was characterize...

Embodiment 2

[0065] The 3-iodochromone in Example 1 was replaced by 3-iodo-5-methoxychromone, and the other conditions were the same as in Example 1 to finally obtain a light green solid with a yield of 43.0 mg and a yield of 60%. , its diastereoselectivity was detected to be 99:1, and its melting point was 175.9~177.1°C.

[0066] The above-mentioned light green solid was characterized by NMR, and the specific result data are as follows:

[0067] 1 H NMR (400MHz, CDCl 3 )δ7.40(t,J=8.4Hz,1H),7.34–7.28(m,2H),7.26–7.21(m,1H),7.15–7.11(m,2H),6.86–6.82(m,1H) ,6.77–6.73(m,1H),3.95(s,3H),3.84–3.81(m,1H),3.25–3.15(m,1H),2.68(d,J=4.2Hz,1H),2.24(d ,J=4.2Hz,1H),2.20–2.15(m,1H),1.66–1.56(m,1H),1.54–1.46(m,1H),1.42–1.31(m,2H),1.18–1.10(m ,2H);

[0068] 13 C NMR (100MHz, CDCl 3 )δ176.9, 167.1, 160.4, 159.6, 142.5, 133.0, 129.0, 127.7, 127.2, 124.7, 115.2, 110.6, 106.4, 57.1, 56.6, 53.2, 49.3, 42.9, 39.0, 32.8, 28.9, 28.I7. ):calcd.for C 24 h 23 o 3 [M+H] + 359.1642; found 359.1645.

[0069]...

Embodiment 3

[0072] The 3-iodochromone in Example 1 was replaced by 3-iodo-6-methylchromone, and other conditions were the same as in Example 1 to finally obtain a yellow solid with a yield of 52.0 mg and a yield of 76%. Its diastereoselectivity was detected to be 81:19, and its melting point was 169.5-171.3°C.

[0073] The above green solid was characterized by NMR, and the specific result data are as follows:

[0074] 1H NMR (400MHz, CDCl 3 )δ8.03–8.00(m,1H),7.36–7.29(m,3H),7.27–7.24(m,1H),7.18(d,J=8.5Hz,1H),7.15–7.13(m,2H) ,3.89–3.85(m,1H),3.29–3.25(m,1H),2.65(d,J=4.2Hz,1H),2.42(s,3H),2.26(d,J=4.3Hz,1H), 2.24–2.19(m,1H),1.66–1.58(m,1H),1.57–1.47(m,1H),1.44–1.31(m,2H),1.22–1.11(m,2H);

[0075] 13 C NMR (100MHz, CDCl 3 )δ176.9, 169.6, 155.6, 142.6, 134.9, 134.2, 129.0, 127.7, 127.2, 125.3, 124.1, 123.3, 118.1, 57.5, 53.0, 49.1, 42.9, 39.2, 32.9, 29.0, 28.7, 21.0 ):calcd.for C 24 h 23 o 2 [M+H] + 343.1693; found 343.1697.

[0076] After analysis, it can be seen that the structu...

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Abstract

The invention discloses a chromone skeleton-containing polycyclic compound as well as a preparation method and application thereof. The preparation method comprises the following steps: with 3-iodochromone compounds and norbornene as building blocks and palladium acetate as a catalyst, carrying out a [2 + 2 + 1] domino cycloaddition reaction with benzyl bromide compounds in an organic solvent to obtain a series of polycyclic compounds containing chromone skeletons, wherein diastereostereoselective change of the product is realized by adjusting the solvent. The chromone skeleton-containing polycyclic compound contains a chromone skeleton with potential biological activity, can provide a compound source for biological activity screening, and has important application value for drug screeningand pharmaceutical industry. Meanwhile, tumor growth inhibition activity screening is carried out on human non-small cell lung cancer cells (A549) and human hepatoma carcinoma cells (HepG2) of two tumor cell strains by the compound, and the compound is found to have certain tumor cell growth inhibition activity and can be applied to preparation of anti-tumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a polycyclic compound containing a chromone skeleton, a preparation method and an application thereof. Background technique [0002] The heterocyclic structure is an important part of the molecular structure of modern drugs, and the existence of the heterocyclic skeleton often determines the important biological and pharmaceutical activities of the drug molecule. New synthetic strategies for the construction of heterocyclic compounds by efficiently synthesizing multiple bonds have far-reaching applications in the synthesis of natural products, bioactive molecules, and functional materials, and are an important goal of modern organic chemistry. Among oxygen-containing heterocyclic compounds, chromones are an important class of structural units, which widely exist in many natural products and drug molecules with important biological activities. Therefore, the developme...

Claims

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Application Information

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IPC IPC(8): C07D311/78A61P35/00
CPCC07D311/78A61P35/00C07B2200/13
Inventor 韩文勇贺晨李菲陈永正崔宝东万南微
Owner ZUNYI MEDICAL UNIVERSITY
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