Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

A technology of aryl sulfonate and compound, applied in medical preparations containing active ingredients, organic chemistry, organic active ingredients, etc.

Active Publication Date: 2018-06-26
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No reports of the replacement of the sulfonamide group in celecoxib by other groups have been seen in the existing literature, and its use as an anti-inflammatory compound that inhibits COX-2

Method used

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  • Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
  • Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
  • Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, the synthesis of phenyl-5-methyl-3-p-tolyl-1-hydropyrazole-1-sulfonate

[0046] (1) Preparation of phenylsulfonyl fluoride: take a 100ml round bottom flask, add a magnet, add phenol (9.4g, 100mmol, 1.0eq) and 50ml of dichloromethane, then add triethylamine (20.8ml, 150mmol, 1.5eq), was introduced into sulfuryl fluoride gas, reacted at room temperature for 2-6h, monitored by TLC plate, extracted with dichloromethane after the reaction was complete, and the solvent was spin-dried to obtain phenylsulfonyl fluoride. Its structural formula and data representation are as follows:

[0047]

[0048] 1 H NMR (300 MHz, CDCl 3 ) δ 7.31 – 7.48 (m, 5H). 19 F NMR (282 MHz, CDCl 3 ) δ37.38;

[0049](2) Preparation of 1-p-methylphenylbutane-1,3-dione: Take a 100ml round bottom flask, add a magnet, and add sodium hydride (1.76g, 44mmol, purity 60%, 1.1eq) into it , then add 50ml of ethyl acetate under ice bath, slowly add p-methylacetophenone (5.37g, 40mmol, 1.0eq...

Embodiment 2

[0058] Embodiment 2, the synthesis of p-iodophenyl-5-methyl-3-p-tolyl-1-hydropyrazole-1-sulfonate

[0059] (1) Preparation of p-iodophenylsulfonyl fluoride: Take a 100ml round bottom flask, add a magnet, add p-iodophenol (4.4g, 20mmol, 1.0eq) and 50ml of dichloromethane, and then add triethylamine (4.2ml, 30mmol, 1.5eq), pass through sulfuryl fluoride gas, react at room temperature for 2-6h, monitor with TLC plate, extract with dichloromethane after the reaction is complete, spin the solvent to obtain p-iodophenylsulfonyl fluoride . Its structure and characterization data are as follows:

[0060]

[0061] 1 H NMR (300 MHz, CDCl 3 ) δ 8.40 (d, J = 7.8 Hz, 2H), 7.56 (d, J = 7.8 Hz,2H). 19 F NMR (282 MHz, CDCl 3 ) δ 37.35;

[0062] (2) Preparation of 1-p-tolylbutane-1,3-dione: same as Example 1;

[0063] (3) Preparation of 3-methyl-5-p-tolyl 1-hydropyrazole: same as Example 1;

[0064] (4) Preparation of p-iodophenyl-5-methyl-3-p-tolyl-1-hydropyrazole-1-sulfonate: ...

Embodiment 3

[0067] Example 3, Preparation of o-iodophenyl-5-methyl-3-p-tolyl-1-hydropyrazole-1-sulfonate

[0068] (1) Preparation of o-iodophenylsulfonyl fluoride: Take a 100ml round bottom flask, add a magnet, add o-iodophenol (11.0g, 50mmol, 1.0eq) and 50ml of dichloromethane, and then add triethylamine (13.9ml, 100mmol, 2.0eq), add sulfuryl fluoride gas, react at room temperature for 2-6h, monitor with TLC plate, extract with dichloromethane after the reaction is complete, and spin to dry the solvent to obtain o-iodophenylsulfonyl fluoride ester;

[0069] (2) Preparation of 1-p-tolylbutane-1,3-dione: same as Example 1;

[0070] (3) Preparation of 3-methyl-5-p-tolyl 1-hydropyrazole: same as Example 1;

[0071] (4) Synthesis of o-iodophenyl-5-methyl-3-p-tolyl-1-hydropyrazole-1-sulfonate: take a 50ml round bottom flask, add magnetons, and add 3-methyl - 5-p-tolyl-1-hydropyrazole (1.72g, 10mmol, 1.0eq) and o-iodophenylsulfonyl fluoride (4.4g, 20mmol, 2.0eq), then potassium tert-butoxide...

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Abstract

The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.

Description

technical field [0001] The present invention relates to a pyrazole compound, in particular to a pyrazole compound containing N-arylsulfonate and a synthesis method thereof; the present invention also relates to the use of the pyrazole compound in the preparation of drugs for inhibiting COX-2-related diseases The application of the invention belongs to the technical field of chemical synthesis and the field of biomedicine. Background technique [0002] Non-steroidal anti-inflammatory drugs can inhibit the cyclooxygenase activity that catalyzes the formation of prostaglandin G and H from arachidonic acid, so they have antipyretic, anti-inflammatory and analgesic effects. So far, studies have found that there are two subtypes of cyclooxygenase isozymes: cyclooxygenase 1 and cyclooxygenase 2, also called COX-1 and COX-2. COX-1 is a structural enzyme that exists in normal tissues. Its physiological function is to catalyze the oxidation of arachidonic acid to generate prostagland...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D405/04C07D409/04C07D401/04A61K31/415A61K31/4155A61K31/4439A61P29/00A61P19/02A61P25/02A61P35/00
CPCC07D231/12C07D401/04C07D405/04C07D409/04
Inventor 王锐许兆青郭全平姚海燕
Owner LANZHOU UNIVERSITY
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