Bromophenol-pyrazoline compound and synthesis method and application thereof

A synthesis method and compound technology, applied in the field of compounds, can solve problems such as repeated infection, difficulty in complete immunity, unsatisfactory treatment effect, etc., and achieve broad application prospects and high-efficiency inhibition of activity

Active Publication Date: 2020-10-30
LEAD HIGH TECH (QINGDAO) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are multiple serotypes of coronavirus, which can cause repeated infections, and it is difficult to achieve complete immunity
At present, there is no specific drug for the treatment of COVID-19 on the market. Broad-spectrum antiviral drugs or traditional Chinese medicine are widely used clinically to treat various symptoms, but the therapeutic effect is not ideal

Method used

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  • Bromophenol-pyrazoline compound and synthesis method and application thereof
  • Bromophenol-pyrazoline compound and synthesis method and application thereof
  • Bromophenol-pyrazoline compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 3,4-dibromo-5-(3-(4-(4-ethoxyphenoxy)phenyl)-4,5-dihydro-1H-pyrazol-5yl)-1 , Synthesis and characterization of 2-dihydroxybenzene (6a)

[0027] (1) Synthetic route and specific steps

[0028]

[0029] Take 15.2g of vanillin (0.1mol, 1) and add it into 100mL of dichloromethane, and stir evenly. Under stirring in an ice bath, a solution of 5.6 mL of bromine (16.0 g, 0.1 mol) in 10 mL of methanol was added dropwise. React at room temperature for 2 hours, then cool to 0°C. 50 mL of ice water was added dropwise, and a precipitate precipitated out, filtered, washed with ice water, and dried to obtain 21 g of white solid 5-bromo-vanillin (2a, yield 92%, mp 160-162°C).

[0030] Add 21g of 5-bromo-vanillin (2a, 0.09mol) into 100mL of acetic acid, and add dropwise a solution of 10.26mL (0.2mol) of bromine in 15mL of acetic acid under normal temperature stirring. Add 0.1 g of reduced iron powder, and reflux for 2 hours. Cool to room temperature, filter the preci...

Embodiment 2

[0038] Example 2: 5-(2,3-dibromo-4,5-dihydroxyphenyl)-3-(4-(4-ethoxyphenoxy)phenyl)-4,5-dihydro- Synthesis and Characterization of 1H-1-Formaldehyde Pyrazole (6b)

[0039] (1) Synthetic route and specific steps

[0040]

[0041] Weigh 267 mg (0.5 mmol) of compound (5a), dissolve it in a mixed solution of 3 mL ethanol and 1 mL formic acid, and add 5 drops of hydrazine hydrate (concentration 85%) under stirring. Heating to reflux for 2h, cooling, and standing overnight. A white solid precipitated, after ultrasonic vibration, filtered, washed with water and ethanol to obtain the final product 5-(2,3-dibromo-4,5-dihydroxyphenyl)-3-(4-(4-ethoxy (phenoxy)phenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (6b), 176 mg (61.1% yield).

[0042] (2) Compound characterization

[0043] 1 H NMR (500MHz, DMSO-d6) δ8.94(s, 1H), 7.75(d, J=8.3Hz, 2H), 7.04(d, J=8.9Hz, 2H), 6.97(dd, J=13.6, 8.8Hz, 4H), 6.53(s, 1H), 5.63(dd, J=11.4, 3.8Hz, 1H), 4.03–4.00(m, 2H), 3.91(dd, J=17.8, 11.8Hz, 1H),...

Embodiment 3

[0045] Example 3: 5-(2,3-dibromo-4,5-dihydroxyphenyl)-3-(4-(4-ethoxyphenoxy)phenyl)-4,5-dihydro- Synthesis and Characterization of 1H-1-Acetylpyrazole (6c)

[0046] (1) Synthetic route and specific steps

[0047]

[0048] Weigh 267 mg (0.5 mmol) of compound (5a), dissolve it in 4 mL of acetic acid solution, and add 5 drops of hydrazine hydrate (concentration 85%) under stirring. Heating to reflux for 2h, cooling, and standing overnight. A white solid precipitated, after ultrasonic vibration, filtered, washed with water and ethanol to obtain the final product 5-(2,3-dibromo-4,5-dihydroxyphenyl)-3-(4-(4-ethoxy (phenoxy)phenyl)-4,5-dihydro-1H-1-acetylpyrazole (6c), 121 mg (yield 41.1%).

[0049] (2) Compound characterization

[0050] 1 H NMR (500MHz, DMSO-d6) δ9.97(s, 1H), 9.54(s, 1H), 7.73(d, J=8.8Hz, 2H), 7.01(d, J=9.0Hz, 2H), 6.98 –6.91(m,4H),6.46(s,1H),5.61(d,J=7.8Hz,1H),4.05–3.98(m,2H),3.89–3.82(m,1H),2.95(dd,J =17.9,4.0Hz,1H),2.31(s,3H),1.31(t,J=7.0Hz,3H).

[005...

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Abstract

The invention relates to a compound, in particular to a bromophenol-pyrazoline compound and a synthesis method and application thereof. The bromophenol-pyrazoline compound provided by the invention has efficient main protease Mpro inhibitory activity, can interfere with the replication of coronavirus in cells, has the effect of treating coronavirus pneumonia, and has a wide application prospect inpreparation of drugs for treating coronavirus pneumonia.

Description

technical field [0001] The invention relates to a compound, especially a bromophenol-pyrazoline compound and its synthesis method and application. Background technique [0002] The new coronavirus is a single-stranded RNA positive-strand enveloped B-coronavirus. In the life cycle of the coronavirus, all replication and transcription are performed by the multi-protein replicase ppla and pplab. Before becoming mature functional proteins, ppla and ppab must be hydrolyzed by the host's cellular enzymes before they can function. This important polyprotein hydrolysis process in the life cycle of the virus is a proteolytic enzyme (Main Protease, M) encoded by the virus. pro ) and is essential for processing polyproteins translated from viral RNA. Therefore, inhibiting the activity of this enzyme will effectively prevent viral replication. [0003] Countries around the world are stepping up the development of vaccines against the novel coronavirus pneumonia, and some vaccines hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06C07D417/04A61K31/415A61K31/427A61P31/14
CPCC07D231/06C07D417/04A61P31/14
Inventor 史大永李祥乾王鑫杨金波
Owner LEAD HIGH TECH (QINGDAO) CO LTD
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