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1,3-benzothiazinone compound as well as synthesis method and application thereof

A technology of benzothiazinone and synthesis method, which is applied in the field of medicinal chemistry, can solve the problems of toxicity and interleukin compensatory increase, and achieve the effect of low toxicity, low toxicity and high yield

Inactive Publication Date: 2019-02-26
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since most non-steroidal anti-inflammatory drugs such as Xicam only inhibit the cyclooxygenase pathway, resulting in a compensatory increase in interleukin produced by the lipoxygenase pathway, resulting in nephrotoxicity, cardiovascular toxicity, etc.

Method used

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  • 1,3-benzothiazinone compound as well as synthesis method and application thereof
  • 1,3-benzothiazinone compound as well as synthesis method and application thereof
  • 1,3-benzothiazinone compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] N-(4-methoxybenzyl)-2-(methylthio)benzamide (Formula 2):

[0036] 1 2 g (6.5 mmol) of 2,2'-dithiodibenzoic acid, 3 g of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCl, 15.7 mmol), 2 g of 1-hydroxybenzotriazole (HOBt, 15.7 mmol) and 2.7 g (19.7 mmol) of 4-methoxybenzyl were placed in a 250 ml round bottom flask and replaced with argon. After adding 60ml of dry dichloromethane as a solvent, put it in an ice bath and stir, and add 3.3g (32.7mmol) of triethylamine dropwise, and then move to room temperature to react overnight. The reaction solution was quenched with saturated ammonium chloride solution, extracted three times with 50ml of dichloromethane, the solvent was evaporated by rotary evaporation, and the product 2 was separated by column chromatography to obtain 1.1g with a yield of 30%.

Embodiment 2

[0038] 2-mercapto-N-(4-methoxybenzyl)benzamide (Formula 3):

[0039]Put compound 2 2,2'-dithio-(4-methoxybenzyl)benzamide 1.1g (2.0mmol) in a 100ml round bottom flask, add 20ml of dry tetrahydrofuran under the protection of argon, and stir in an ice bath . Then slowly add 300 mg (8.0 mmol) of sodium borohydride, and quench the reaction with 5M / L hydrochloric acid under ice-cooling after 5 minutes. After the tetrahydrofuran was evaporated by rotary evaporation, it was extracted three times with dichloromethane, the solvent was evaporated by rotary evaporation, and 1 g of the product was obtained by silica gel column chromatography with a yield of 90%.

Embodiment 3

[0041] 3-(4-methoxybenzyl)-2-methyl-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one (formula 4, R 1 =CH 3 ):

[0042] Add compound 3 2-mercapto-(4-benzylmethoxybenzyl) benzamide 1g (3.6mmol), p-toluenesulfonic acid 620mg (3.6mmol), 160mg acetaldehyde (3.6mmol) and 35ml toluene in a 100ml round bottom flask , react overnight at 30°C under the protection of argon. After TLC traced the disappearance of the raw material, the toluene was evaporated by rotary evaporation, and extracted three times with dichloromethane. After the solvent was evaporated, the column was separated by column chromatography to obtain 750 mg of white solid with a yield of 70%.

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Abstract

The invention discloses a 1,3-benzothiazinone compound which has a chemical structural formula as shown in the description, in the formula, R1 is C1-C4 straight chain alkyl or methyl carbethoxy respectively; and R2 is a heterocyclic compound or substituted phenyl. The compound disclosed by the invention has activity equivalent to or higher than those of known medicines such as meloxicam and piroxicam at a cell level, has anti-inflammation, anti-cancer and antibacterial activity, has toxicity lower than those of xicam compounds in the market, and is safe and effective.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pharmacologically active 1,3-benzothiazinone compound and its synthesis method and application. Background technique [0002] Benzothiazinone has a wide range of biological activities. Studies have found that such derivatives have antibacterial, anticancer, anti-inflammatory, diuretic and blood lipid-lowering effects. Among them, a class of compounds in the 1,2-benzothiazinone compound has obvious anti-inflammatory effect, and the representative drug is a non-steroidal anti-inflammatory drug of the Xicam class. Xicam anti-inflammatory drugs act on the body's cyclo-oxygen-ase (COX), and inhibit the synthesis of prostaglandins by inhibiting the cyclo-oxygen-ase (COX) metabolism of cyclo-oxygen-ase, thereby exerting anti-inflammatory and analgesic effects. Its representative drugs are meloxicam and piroxicam. Its structural formula is as follows: [0003] . ...

Claims

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Application Information

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IPC IPC(8): C07D279/08C07D417/12A61K31/5415A61K31/541A61P35/00A61P35/02A61P29/00A61P31/02A61P31/04A61P31/10
CPCA61P29/00A61P31/02A61P31/04A61P31/10A61P35/00A61P35/02C07D279/08C07D417/12Y02P20/55
Inventor 王震侯永胜范晓红李俊芳邓杰丹
Owner LANZHOU UNIVERSITY
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