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3-(d-glucopyranosyl)thiazole derivative and its preparation method and application

A technology of glucopyranosyl and derivatives, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of few types and low content, and achieve good inhibitory effect

Active Publication Date: 2012-02-08
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, naturally occurring glycosyl heterocyclic compounds containing thiazole rings are not only rare in species and low in content, but far from meeting the needs of research. Therefore, glycosyl heterocyclic compounds containing thiazole rings are mostly synthesized.

Method used

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  • 3-(d-glucopyranosyl)thiazole derivative and its preparation method and application
  • 3-(d-glucopyranosyl)thiazole derivative and its preparation method and application
  • 3-(d-glucopyranosyl)thiazole derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of 1-benzoyl-4-methyl-3-(D-glucopyranosyl)thiazole compound

[0030] At a certain temperature (60°C), prepare 10ml of a KOH / EtOH solution with a concentration of 0.1g / ml, and then add 716mg (1mmol) of 1-benzoyl-4-methyl-3-(2,3,4,6- Tetra-O-pivaloyl-D-glucopyranosyl)thiazole was stirred for 5 hours, detected by TLC spot plate, using a mixed solution of ethyl acetate and methanol with a volume ratio of 10:1 as the developer, after the reaction was complete, 2N Hydrochloric acid until the pH value is 7, and the solvent is removed by a rotary evaporator to obtain a yellow solid, which is completely dissolved by adding 10ml of methanol, filtered, and the filtrate is concentrated to a solid, then dry-loaded, and the volume ratio of ethyl acetate and methanol is 10: The mixed solution of 1 was the eluent, and column chromatography gave 309 mg of white solid, with a yield of 81.4%; mp 126-128°C. 1 H NMR (CD 3 OD): δ7.96(d, J=8Hz, 2H), 7.55-7.43(m, 3H), ...

Embodiment 2

[0031] Example 2: Preparation of 1-benzoyl-4-(4-iodophenyl)-3-(D-glucopyranosyl)thiazole compound

[0032] At a certain temperature (20°C), prepare MeNH with a concentration of 0.2g / ml 2 / MeOH solution 10ml, then add 904mg (1mmol) 1-benzoyl-4-(4-iodophenyl)-3-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranose Base) thiazole was stirred for 4 hours, and detected by TLC spot plate, using a mixed solution of ethyl acetate and methanol with a volume ratio of 10:1 as the developing solvent. The solvent was removed to obtain a yellow solid, which was completely dissolved by adding 10ml of methanol, filtered, and the filtrate was concentrated to a solid, then dry-loaded, using a mixed solution of ethyl acetate and methanol with a volume ratio of 10:1 as the eluent, and obtained by column chromatography White solid 352mg, yield 62.0%; mp 179-181°C; 1 H NMR (CD 3 OD): δ8.01(q, J=8.2Hz, 2H), 7.68(t, J=6.0Hz, 4H), 7.65(d, J=8.8Hz, 1H), 7.56(q, J=6.6Hz, 2H), 6.01.(d, J=6.2Hz, 1H), 5.6(t, J=8.4...

Embodiment 3

[0033] Example 3: Preparation of 1-benzoyl-4-(4-nitrophenyl)-3-(D-glucopyranosyl)thiazole compound

[0034] At a certain temperature (40°C), prepare Me with a concentration of 0.3g / ml 2 NH / MeOH solution 10ml, then add 823mg (1mmol) 1-benzoyl-4-(4-nitrophenyl)-3-(2,3,4,6-tetra-O-pivaloyl-D-pyridine Glucopyranosyl)thiazole was stirred for 4 hours, detected by TLC spot plate, using a mixed solution of ethyl acetate and methanol with a volume ratio of 10:1 as the developing solvent, after the reaction was complete, 2N hydrochloric acid was added to pH 7, and the solvent was rotated to Remove solvent by evaporator to obtain yellow solid, add 10ml of methanol to dissolve completely, filter, concentrate the filtrate to solid, apply dry method, use ethyl acetate and methanol volume ratio 10:1 mixed solution as eluent, column layer Analysis gave 334.5mg of white solid, yield rate was 68.7%; mp101-103°C; 1 H NMR (CD 3 OD): δ7.96(q, J=4.4Hz, 2H), 7.54(t, J=6.2Hz, 4H), 7.38(d, J=10.2Hz...

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Abstract

The invention discloses a 3-(D-glucopyranosyl)thiazole derivative as shown in formula (VII); in formula (VII), R1 is benzoyl, formyl or acetyl; R2 is methyl, Ethyl, acetyl, fluorophenyl, chlorophenyl, iodophenyl, methoxyphenyl or nitrophenyl; R3 is hydrogen, methyl, ethyl or phenyl, and discloses 3-(D- A preparation method of glucopyranosyl)thiazole derivatives and an application thereof in the preparation of antitumor drugs. The beneficial effects of the present invention are: providing a new 3-(D-glucopyranosyl)thiazole derivative with anticancer activity, which has a good inhibitory effect on HCT-8 cells and can be applied to the preparation of antitumor drugs middle.

Description

(1) Technical field [0001] The present invention relates to a novel 3-(D-glucopyranosyl)thiazole derivative, its preparation method, and its application in the preparation of antitumor drugs. (2) Background technology [0002] Carbohydrates are a large class of organic compounds with broad-spectrum chemical structures and biological functions that exist in nature, and have important and complex physiological functions and physiological activities in the body. Studies have found that many carbohydrate compounds have antibacterial, antiviral, and antitumor activities, but their application as drugs is limited because they also bring toxic side effects to the body while treating diseases. Chemical modification of sugar and its derivatives can improve biological activity and reduce toxic side effects, so it has attracted great attention. [0003] Many natural compounds contain thiazole rings, such as LyngbyabellinA, Dollarbellin, etc., from which drugs with physiological activi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/24C07H1/00A61K31/7056A61P35/00
Inventor 章鹏飞赵卿郑辉
Owner HANGZHOU NORMAL UNIVERSITY
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