Thiazole (piperazine) azululanone azasugar derivative and synthesis method and application thereof to medicinal preparation

A technology of derivatives and azasaccharides, applied in the direction of active ingredients of heterocyclic compounds, medical preparations containing active ingredients, antiviral agents, etc., to achieve the effect of simple operation

Inactive Publication Date: 2012-04-18
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current research focuses on the heterocyclic rings of azasaccharides, and its transformation is mainly pyrrole, pyridine, i

Method used

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  • Thiazole (piperazine) azululanone azasugar derivative and synthesis method and application thereof to medicinal preparation
  • Thiazole (piperazine) azululanone azasugar derivative and synthesis method and application thereof to medicinal preparation
  • Thiazole (piperazine) azululanone azasugar derivative and synthesis method and application thereof to medicinal preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Synthesis of 6R, 7R, 8R, 8aR)-tetrahydro-6-hydroxyl-7,8-O-isopropyl-2H-thiazo[3,2-a]pyridin-3(5H)-one (referred to as compound 2a) and (6R, 7R, 8R, 8aS)-tetrahydro-6-hydroxyl-7,8-O-isopropyl-2H-thiazo[3,2-a]pyridin-3(5H)-one (referred to as compound 3a )

[0060] Its chemical reaction formula is as follows:

[0061]

[0062] The specific method is:

[0063] In a 10mL microwave sealed tube, weigh 1mmol azido sugar 1a (1-hydroxy-2,3-O-isopropyl-5-azidofuran D ribose), and dissolve it in 3mL anhydrous toluene, add Triphenylphosphine 393mg (1.5mmol), microwave irradiation at 80°C for 5-8min., add thioglycolic acid 146μL (2.0mmol), continue microwave reaction at 80°C for 10-15min. After the reaction was completed, anhydrous potassium carbonate powder was added to neutralize the reaction solution to pH=7, and dichloromethane (3×10 mL) was added for extraction, the organic phases were combined, and silica gel column chromatography (ethyl acetate:cyclohexane 1:3-2:1), to...

Embodiment 2

[0079] Synthesis of (6R, 7S, 8S, 8aR)-tetrahydro-6-hydroxyl-7,8-O-isopropyl-2H-thiazo[3,2-a]pyridin-3(5H)-one (referred to as compound 2b ) and (6R, 7S, 8S, 8aS)-tetrahydro-6-hydroxyl-7,8-O-isopropyl-2H-thiazolo[3,2-a]pyridin-3(5H)-one (compound for short 3b)

[0080] Its chemical reaction formula is as follows:

[0081]

[0082] The specific method is:

[0083] In a 10 mL microwave sealed tube, weigh 1 mmol of azido sugar 1b (2,3-O-isopropyl-5-azidofuran D-lyxose), dissolve it in 3 mL of anhydrous toluene, add triphenyl Base phosphine 393mg (1.5mmol), seal the tube at 80°C for 5-8min under microwave irradiation, add 146μL (2.0mmol) of thioglycolic acid, and continue the microwave seal reaction at 80°C for 10-15min. After the reaction was completed, anhydrous potassium carbonate powder was added to neutralize the reaction solution to pH=7, and dichloromethane (3×10 mL) was added for extraction, the organic phases were combined, and silica gel column chromatography (ethyl...

Embodiment 3

[0105] Synthesis of (5S,6R,7S,8S,8aR)-tetrahydro-5-trityloxymethyl-6-hydroxy-7,8-O-isopropyl-2H-thiazole[3,2-a] Pyridin-3(5)-one (compound 2c for short) and (5S,6R,7S,8S,8aS)-tetrahydro-5-trityloxymethyl-6-hydroxy-7,8-O-iso Propyl-2H-thiazo[3,2-a]pyridin-3(5H)-one (compound 3c for short)

[0106] Its chemical reaction process is as follows:

[0107]

[0108] The specific method is:

[0109] In a 10 mL microwave sealed tube, weigh 1 mmol azido sugar 1c (2,3-O-isopropyl-5-azido-6-O-tritylfuran D-mannose), and dissolve it in 3 mL Add 393 mg (1.5 mmol) of triphenylphosphine to anhydrous toluene, seal the tube at 80°C for microwave irradiation for 5-8 min., add 146 μL (2.0 mmol) of thioglycolic acid, and continue the microwave lock reaction at 80°C for 10-15 min. After the reaction was completed, anhydrous potassium carbonate powder was added to neutralize the reaction solution to pH=7, and dichloromethane (3×10 mL) was added for extraction, the organic phases were combined, ...

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Abstract

The invention discloses a thiazole (piperazine) azululanone azasugar derivative, and provides a synthesis method of the derivative and application of the derivative to preparation of an anti-HIV (Human Immunodeficiency Virus) medicinal preparation. A compound has high anti-HIV activity, and more administration options can be provided for clinical treatment of AIDS.

Description

technical field [0001] The present invention relates to an azasaccharide derivative compound and its synthesis method and its application in pharmaceutical preparations, in particular to thiazolyl (oxazin) alkanone azasaccharides, its synthesis method and its application in pharmaceutical preparations. Background technique: [0002] AIDS is acquired immunodeficiency syndrome (Acquired Immunodeficiency Syndrome, AIDS), is caused by human immunodeficiency virus (Human Immunodeficiency Virus, HIV) infection. There are three main classes of drugs currently used to treat AIDS: nucleoside reverse transcriptase inhibitors, non-nucleoside reverse transcriptase inhibitors, and protease inhibitors. Because HIV has a very strong ability to mutate rapidly, patients will develop drug resistance shortly after taking certain anti-HIV drugs. For this reason, clinicians often use more than three different anti-HIV drugs in combination. Even so, patients will still develop obstinate drug re...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/437A61K31/542A61K31/55A61P31/18
CPCY02P20/55
Inventor 李小六陈华张洪志秦占斌张平竹殷庆梅张金超
Owner HEBEI UNIVERSITY
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