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(Thio) barbituric acid compound and application thereof

A technology of compounds and uses, applied in the field of chemical medicine, can solve problems such as increasing energy consumption, and achieve significant effects

Inactive Publication Date: 2013-06-26
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2. Drugs that increase energy expenditure

Method used

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  • (Thio) barbituric acid compound and application thereof
  • (Thio) barbituric acid compound and application thereof
  • (Thio) barbituric acid compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation of Example 1 "N-phenyl-2-(4-((2,4,6-trioxotetrahydropyrimidine-5(2H)-methylene) methyl)phenoxy)acetamide" .

[0057]

[0058] Step 1: Synthesis of 2-chloro-N-phenylacetamide.

[0059] Under ice-bath stirring, aniline (1.86g, 20mmol) and triethylamine (24mmol, 3.3ml) were dissolved in anhydrous dichloromethane (20ml), then chloroacetyl chloride (2.71g, 24mmol) was slowly added dropwise into the above solution. The mixture was stirred at room temperature for 12 hours. Then the solvent was removed under reduced pressure, the obtained solid was washed with ice water (100ml), filtered, and finally the crude product was recrystallized with diethyl ether / petroleum ether mixed solvent to obtain 3.1 g of white solid (yield 92%).

[0060] NMR: (400MHz, CDCl 3 )δ8.232 (s, 1H), 7.562-7.540 (m, 2H), 7.385-7.341 (m, 2H), 7.199-7.156 (m, 1H), 4.195 (s, 2H);

[0061] Mass Spectrum: 170.01[M+H] + .

[0062] Step 2: Synthesis of 2-(4-formylphenoxy)-N-phenylacetamide...

Embodiment 2

[0070] Example 2 "2-(4-((4,6-dioxo-2-thiotetrahydropyrimidine-5(2H)-methylene)methyl)phenoxy)-N-phenylacetamide" preparation of

[0071]

[0072] Step 1: Synthesis of 2-chloro-N-phenylacetamide.

[0073] Under ice-bath stirring, aniline (1.86g, 20mmol) and triethylamine (24mmol, 3.3ml) were dissolved in anhydrous dichloromethane (20ml), then chloroacetyl chloride (2.71g, 24mmol) was slowly added dropwise into the above solution. The mixture was stirred at room temperature for 12 hours. Then the solvent was removed under reduced pressure, the obtained solid was washed with ice water (100ml), filtered, and finally the crude product was recrystallized with diethyl ether / petroleum ether mixed solvent to obtain 3.1 g of white solid (yield 92%).

[0074] NMR: (400MHz, CDCl 3 )δ8.232 (s, 1H), 7.562-7.540 (m, 2H), 7.385-7.341 (m, 2H), 7.199-7.156 (m, 1H), 4.195 (s, 2H);

[0075] Mass Spectrum: 170.01[M+H] + .

[0076] Step 2: Synthesis of 2-(4-formylphenoxy)-N-phenylacetamid...

Embodiment 3

[0085] Example 3 Preparation of "N-p-toluene-2-(4-((2,4,6-trioxotetrahydropyrimidine-5(2H)-methylene)methyl)phenoxy)acetamide"

[0086]

[0087] Yield: 78.0%; Purity: 98.39%; Yellow solid; NMR (400MHz, DMSO-d 6 ): δ11.319(s, 1H), 11.194(s, 1H), 10.084(s, 1H), 8.358(d, 2H, J=9.2Hz), 8.251(s, 1H), 7.510(d, 2H, J=8.4Hz), 7.120(t, 4H, J=8.0Hz), 4.838(s, 2H), 2.257(s, 3H);

[0088] Mass spectrum: 378.15[M+H] - .

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Abstract

The invention relates to a (thio) barbituric acid compound and an application thereof, and belongs to the field of chemical medicine. Particularly, the invention relates to a compound as shown in formula I and an application thereof, wherein R1 is hydrogen or methyl; R2 is a benzene ring containing different substituents, a pyridine ring containing different substituents, cyclohexyl, pyrimidinyl, benzyl or a naphthalene ring group; R3, R4, R5, R6 and R7is hydrogen or a methyl; X is oxygen or sulfur atom. Tests show that the compound as shown in formula I has good effect on treating metabolic diseases such as diabetes, obesity, and the like, and provides a new choice for the preparation of drugs for treating metabolic diseases.

Description

technical field [0001] The present invention relates to a new class of (thio)barbituric acid compounds and uses thereof, in particular to 2-(4-(((thio)barbituric acid-5(2H)-methylene)methyl ) phenoxy) acetamide derivatives and their use in the preparation of drugs for the prevention and treatment of obesity and other metabolic diseases, belonging to the field of chemical medicine. technical background [0002] The World Health Organization has defined obesity as a disease, which is the third biggest enemy to human health after cardiovascular and cerebrovascular diseases and cancer. Obese people are prone to high blood pressure, coronary heart disease, fatty liver, diabetes, hyperlipidemia, gout and other diseases. Through clinical tests, the vast majority of patients with simple obesity have endocrine disorders, especially hyperinsulinemia, abnormal glucose tolerance test, disordered sex hormone levels, high adrenal cortex hormones, increased leptin, etc.; [0003] Obesity...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/62C07D239/66C07D401/12A61K31/515A61P3/00A61P3/04A61P3/10A61P9/12A61P3/06A61P1/16
Inventor 陈俐娟魏于全罗有福蒋维
Owner SICHUAN UNIV