Nitroethylene-containing ester compound as well as preparation method and application thereof

A technology of ester compounds and nitroethylene, applied in the field of fructose-1,6-bisphosphatase inhibitors

Inactive Publication Date: 2017-06-13
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few drugs in the prior art that can be used for the treatment or prevention of diabetes and can also treat or prevent thrombosis and hyperlipidemia complications caused by diabetes.

Method used

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  • Nitroethylene-containing ester compound as well as preparation method and application thereof
  • Nitroethylene-containing ester compound as well as preparation method and application thereof
  • Nitroethylene-containing ester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0046] According to another preferred embodiment of the present invention, the ester compound is selected from the compounds described in the following formula:

[0047]

[0048] The present invention also provides a method for preparing the above-mentioned ester compound, the method comprising:

[0049] 1) In the presence of an alkali metal salt and a first organic solvent, the phenolic compound represented by the formula (1') is subjected to a substitution reaction with ethyl 2-halo-2-methylpropionate to obtain the formula (1") the indicated compound;

[0050]

[0051] Among them, R 1' -R 5' At least one of them is -CHO, and the remaining groups are independently selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, -NO 2 , -COOH, -CN, -NR 2 , a C1-C6 alkyl group substituted by a substituent and a C1-C6 alkoxy group substituted by a substituent, R is selected from a C1-C6 alkyl group substituted or unsubstituted by a substituent, each of the substituents independen...

Embodiment 1

[0111] This example is used to illustrate the preparation of the ester compound represented by formula (1-1) of the present invention.

[0112] (1) Mix 0.701g (5mmol) of 4-fluoro-3-formylphenol, 10mmol of potassium carbonate and 25mL of acetonitrile, then add 1.5mL (about 10mmol) of ethyl 2-bromo-2-methylpropionate, and then Heat to reflux at 80°C for 6h; then cool the reaction solution to room temperature (about 25°C), filter with suction and wash the filter cake. The filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. 20 mL of water and ethyl acetate (20 mL×3) were added for extraction, the organic phases were combined and washed with 20 mL of saturated brine, and the organic phase was dried over anhydrous sodium sulfate. Concentrate the dried organic phase, and purify the obtained concentrated solution by silica gel column chromatography (the eluent is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:4) t...

Embodiment 2

[0117] This example is used to illustrate the preparation of the ester compound represented by formula (1-2) of the present invention.

[0118] According to the method described in embodiment 1, the difference is,

[0119] In step (1), 4-chloro-3-formylphenol is used to replace 4-fluoro-3-formylphenol, thereby obtaining the compound (4.1mmol, yield rate 82%) shown in formula (1 "-2) ).

[0120] In step (2), then adopt the compound shown in formula (1 "-2) to replace the compound shown in formula (1 "-1), thereby make the ester compound (2.3mmol) shown in formula (1-2) , the yield was 77%).

[0121] 1 H NMR (600MHz, CDCl 3 )δ8.32(d, J=13.7Hz, 1H), 7.51(d, J=13.7Hz, 1H), 7.34(d, J=8.9Hz, 1H), 7.11(d, J=2.8Hz, 1H) ,6.90(dd,J=8.8,2.8Hz,1H),4.25(q,J=7.1Hz,2H),1.62(s,6H),1.26(t,J=7.1Hz,3H).

[0122] 13 C NMR (151MHz, CDCl 3 )δ173.44, 154.46, 138.85, 134.94, 131.01, 128.96, 128.83, 123.19, 118.89, 79.91, 61.75, 25.24, 14.08.

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Abstract

The invention relates to the field of fructose-1,6-biphosphatase inhibitors, and specifically discloses a nitroethylene-containing ester compound. The ester compound is the compound as shown in a formula (1). The invention further discloses a preparation method of the compound as shown in the formula (1). The invention further discloses another nitroethylene-containing ester compound which is the compound as shown in the formula (2). The invention further discloses a preparation method of the compound as shown in the formula (2). The invention further provides application of the nitroethylene-containing ester compounds or pharmaceutically acceptable salt in preparation of medicines such as the medicine for inhibiting fructose-1,6-biphosphatase, and the medicine for treating or preventing gluconeogenesis metabolic disease or thrombus diseases.

Description

technical field [0001] The invention relates to the field of fructose-1,6-bisphosphatase inhibitors, in particular to ester compounds containing nitrovinyl groups and their preparation methods and applications. Background technique [0002] Diabetes has now been recognized by the World Health Organization and other organizations as a worldwide disease, and will be one of the most important diseases that will cause death or loss of life in the next 30 years. The human liver is an important place for the main production of endogenous glucose. Existing studies have shown that the production of endogenous glucose in the liver is the main reason for the increase in blood sugar in diabetic patients, especially the increase in fasting blood sugar. There are two ways for the liver to produce glucose: one is the endogenous synthesis of glucose, that is, gluconeogenesis; the other is the decomposition of liver glycogen. Inhibiting and regulating the gluconeogenesis pathway and reduci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/32C07C205/37C07C205/53C07C205/54C07C213/08C07C217/84A61K31/22A61K31/277A61K31/222A61P3/10A61P7/02A61P3/06A61P3/04A61P1/16A61P9/00A61P9/10
CPCC07C205/32C07C205/37C07C205/53C07C205/54C07C217/84
Inventor 万坚韩新亚陈海峰黄运远池波任彦亮冯玲玲饶立
Owner HUAZHONG NORMAL UNIV
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