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Piperazine amide compounds containing benzdioxan skeleton and preparation method and application thereof

A technology of benzodioxane and piperazine amide, which is applied in the field of piperazine amide compounds and their preparation, can solve the problems of no piperazine amide compounds, etc. high rate effect

Active Publication Date: 2018-07-31
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report about piperazine amides containing benzodioxane skeleton

Method used

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  • Piperazine amide compounds containing benzdioxan skeleton and preparation method and application thereof
  • Piperazine amide compounds containing benzdioxan skeleton and preparation method and application thereof
  • Piperazine amide compounds containing benzdioxan skeleton and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 2-(5-(2,3-dihydrobenzo[1,4]dioxane)-1,3,4-oxadiazole-2-thione)-1-(4-(2-methoxy The preparation of base phenyl) piperazine) ethanone, its molecular formula is:

[0033]

[0034] (1) Dissolve 10mmol of 1,4-benzodioxanecarbohydrazide and 12mmol of potassium hydroxide in 50mL of methanol, add 100mmol of carbon disulfide dropwise in an ice-water bath, and control the dropping within 15 minutes. After the dropwise addition of carbon disulfide, reflux React for 8 hours, spin to dry the solvent, add water to dissolve, filter, add hydrochloric acid to the filtrate, and filter to obtain product a;

[0035] (2) Dissolve 8mmol o-methoxyphenylpiperazine and 9.6mmol triethylamine in 32mL dichloromethane, slowly add 9.6mmol chloroacetyl chloride dropwise under ice-bath conditions, and control the dripping within 3 minutes; ice-bath conditions Under stirring reaction for 10 hours, filter to obtain product b;

[0036] (3) Dissolve 4mmol of product a, 4mmol of product b, and 6mmol o...

Embodiment 2

[0042] 2-(5-(2,3-dihydrobenzo[1,4]dioxane)-1,3,4-oxadiazole-2-thione)-1-(4-(3-methoxy The preparation of base phenyl) piperazine) ethanone, its molecular formula is:

[0043]

[0044] (1) Dissolve 10mmol of 1,4-benzodioxanecarbohydrazide and 13mmol of potassium hydroxide in 60mL of methanol, add 100mmol of carbon disulfide dropwise in an ice-water bath, and finish dropping within 18 minutes. After adding carbon disulfide dropwise, react under reflux for 9 hours, spin dry the solvent, add water to dissolve, filter, add hydrochloric acid to the filtrate to acidify, and filter to obtain product a;

[0045](2) 8 mmol of m-methoxyphenylpiperazine and 11 mmol of triethylamine were dissolved in 32 mL of dichloromethane, and 11 mmol of chloroacetyl chloride was slowly added dropwise under ice-bath conditions, and the drop was completed within 4 minutes. The reaction was stirred for 11 hours under ice-bath conditions, and filtered to obtain product b;

[0046] (3) 4mmol product a,...

Embodiment 3

[0052] 2-(5-(2,3-dihydrobenzo[1,4]dioxane)-1,3,4-oxadiazole-2-thione)-1-(4-(4-methoxy The preparation of base phenyl) piperazine) ethanone, its molecular formula is:

[0053]

[0054] (1) Dissolve 10mmol of 1,4-benzodioxanecarbohydrazide and 15mmol of potassium hydroxide in 70mL of methanol, add 100mmol of carbon disulfide dropwise in an ice-water bath, and finish dropping within 20 minutes. After adding carbon disulfide dropwise, reflux for 10 hours, spin to dry the solvent, add water to dissolve, filter, add hydrochloric acid to the filtrate to acidify, and filter to obtain product a;

[0055] (2) Dissolve 8 mmol of p-methoxyphenylpiperazine and 12 mmol of triethylamine in 32 mL of dichloromethane, slowly add 12 mmol of chloroacetyl chloride dropwise under ice-bath conditions, and finish the dropping within 5 minutes. Stir the reaction under ice bath conditions for 12 hours, filter to obtain product b;

[0056] (3) 4mmol product a, 4mmol product b, 6mmol potassium hydro...

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Abstract

The invention belongs to the technical field of non-steroidal anti-inflammatory drugs, and particularly relates to piperazine amide compounds containing a benzdioxan skeleton and a preparation methodand application thereof. The preparation method of the piperazine amide compounds containing the benzdioxan skeleton comprises the steps that 1,4-Benzodioxan Formylhydrazine is mixed with potassium hydroxide and methyl alcohol, under an ice-water bath, carbon disulfide is dropwise added, a backflow reaction is performed, a solvent is spin-dried, water is added for filtering, a filtrate is acidized, and a product a is obtained; piperazine substitutes, triethylamine and dichloromethane are mixed, chloroacetyl chloride is dropwise added under the ice-water bath, a reaction is performed, filteringis performed, and a product b is obtained; the product a, the product b, potassium hydroxide and methyl alcohol are mixed, and a reaction is performed to obtain the piperazine amide compounds. The piperazine amide compounds containing the benzdioxan skeleton are easy to synthesize, convenient to purify, high in yield and good in stability in air; the preparation method is simple and easy to implement and suitable for being produced industrially; in addition, the piperazine amide compounds containing the benzdioxan skeleton have the good anti-inflammatory activity and can be used for preparingnon-steroidal anti-inflammatory drugs.

Description

technical field [0001] The invention belongs to the technical field of non-steroidal anti-inflammatory drugs, and in particular relates to a piperazine amide compound containing a benzodioxane skeleton and a preparation method and application thereof. Background technique [0002] Inflammation is the body's own defense mechanism against infection, mainly manifested as redness, swelling, pain and fever. Non-steroidal anti-inflammatory drugs (NSAIDs), such as indomethacin, ibuprofen, naproxen, and fenbufen, are the most commonly used first-line drugs in clinical treatment of inflammation. According to incomplete statistics, more than 100 million people in the world are using such drugs. As the first-line anti-inflammatory and analgesic drugs, NSAIDs have prominent adverse reactions and side effects. Therefore, it is of great significance to develop non-steroidal anti-inflammatory drugs with high efficiency and few side effects. [0003] The benzodioxane skeleton has a very ...

Claims

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Application Information

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IPC IPC(8): C07D413/04A61P29/00
CPCC07D413/04
Inventor 刘志平闫瑞朱家伟岳梦琳田荣威李勇强吴孝婧秦洁
Owner PINGDINGSHAN UNIVERSITY
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