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Benzothiazinethione derivatives and their preparation and use

A technology of benzothiazinethione and its derivatives, which is applied in the field of medicine and can solve the problems of restricting sustainable economic development and long treatment cycle of tuberculosis

Active Publication Date: 2011-12-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional long treatment cycle for tuberculosis has brought enormous pressure to society and families, and has restricted the sustainable development of my country's economy to a certain extent.

Method used

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  • Benzothiazinethione derivatives and their preparation and use
  • Benzothiazinethione derivatives and their preparation and use
  • Benzothiazinethione derivatives and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Example 1 Compound I a: Preparation of 2-(5-bromopyridine-2-amino)-6,7,8-trifluoro-4H-benzo[e][1,3]thiazine-4-thione

[0104]

[0105] Dissolve 2,3,4,5-tetrafluorobenzoyl chloride (3g, 14.12mmol) in dichloromethane (20ml), slowly drop in ammonium thiocyanate (2.14g, 28.24mmol), then add dropwise PEG-400 (0.2g), reacted at room temperature for two hours, filtered off the precipitate, and slowly added the filtrate dropwise to a dichloromethane solution of 2-amino-5-bromo-pyridine (2.44g, 14.12mmol), and reacted at room temperature for three hours. Water and dichloromethane were added to the reaction solution at room temperature, the organic layer was collected and spin-dried to obtain a yellow intermediate, which was placed in a dry flask, Lawson's reagent (5.72g, 14.12mmol) and toluene (80ml) were added, and refluxed for 40 minutes , the reaction solution was cooled and filtered, and the filtrate column chromatography gave 3.15 g of a dark red solid (55.1% yield).

...

Embodiment 2

[0108] Example 2 Compound I b: 6,8-dinitro-2-(4-(trifluoromethyl)anilino)-4H-benzo[e][1,3]thiazine-4-thione preparation

[0109]

[0110] Dissolve 2-chloro-3,5-dinitrobenzoyl chloride (3g, 11.32mmol) in toluene (20ml), slowly drop in ammonium thiocyanate (1.71g, 22.64mmol), then add 18-crown- 6 (0.2g), react at room temperature for about two hours, remove the precipitate by filtration, slowly add p-trifluoromethylaniline (1.82g, 11.32mmol) in toluene solution dropwise, and react at room temperature for two hours. Add water (20ml) to the reaction solution at room temperature, stir for 30 minutes, extract with ethyl acetate, collect the organic layer and spin dry to obtain a yellow intermediate, which is placed in a dry flask, and Lawson's reagent (4.59g, 11.32mmol) is added and toluene (70ml), refluxed for 30 minutes, the reaction solution was cooled and filtered, the filtrate was concentrated to obtain a crude product, and column chromatography gave a red solid 3.20g (66.7...

Embodiment 3

[0113] Example 3 Compound Ic: Preparation of 2-(ethylamino)-6,8-dinitro-4H-benzo[e][1,3]thiazine-4-thione

[0114]

[0115] Dissolve 2-chloro-3,5-dinitrobenzoyl chloride (3g, 11.32mmol) in dichloromethane (20ml), slowly drop in ammonium thiocyanate (1.71g, 22.64mmol), then add peg- 400 (0.2g), react at room temperature for about two hours, remove the precipitate by filtration, slowly add ethylamine solution (0.51g, 11.32mmol) dropwise to the solution, and react at room temperature for two hours. Add water (20ml) to the reaction solution at room temperature, and stir for 30 Minutes, extracted with dichloromethane, collected the organic layer and spin-dried to obtain a yellow intermediate, which was placed in a dry flask, added Lawson's reagent (4.59g, 11.32mmol) and toluene (70ml), refluxed for 30 minutes, and the reaction solution was After cooling and filtration, the filtrate was concentrated to obtain a crude product, and column chromatography gave 1.04 g of a red solid (yi...

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Abstract

The invention belongs to the medicine field, and particularly relates to benzothiazinethione derivatives and preparation methods and uses thereof. In the aspect of the present invention, novel benzothiazinethione derivatives of formula I are provided, the benzothiazinethione derivatives of the invention are new compounds obtained based on extensive screening. Experimental results show that the benzothiazinethione derivatives of formula I have obvious inhibitory effects on mycobacterium tuberculosis, with effects equivalent to or even better than that of isoniazide (MIC 90 =0.8µM). The benzothiazinethione derivatives of formula I have anti-mycobacterium tuberculosis activities, and provide new choices for the development and application of antitubercular agents.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to benzothiazinethione derivatives and their preparation methods and applications. Background technique [0002] Tuberculosis is one of the diseases with the highest morbidity and mortality in history. In the 21st century, tuberculosis remains the leading cause of death in developing countries and a reactivated disease in developed countries. Due to the prevalence of poverty and AIDS, the emergence of multidrug-resistant (MDR-TB) / extensively drug-resistant tuberculosis (XDR-TB), the number of deaths from tuberculosis continues to increase globally, and the existing anti-tuberculosis drugs can no longer meet the needs of cure. At present, one-third of the world's population, that is, 2 billion people, carry Mycobacterium tuberculosis, and tuberculosis kills 3 million people every year, and tuberculosis is likely to sweep the world again. As one of the developing countries, China currently h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D279/08C07D491/113A61K31/5415A61P31/06
CPCC07D417/12C07D417/04C07D491/113C07D279/08A61K31/5415A61P31/06
Inventor 余洛汀魏于全
Owner SICHUAN UNIV
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