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Barbituric acid derivatives and preparation method thereof

A technology of barbituric acid and dimethyl barbituric acid, which is applied in the field of barbituric acid derivatives containing thiophene and fluorine substitution and its preparation, to achieve high yield, strong inhibitory effect, and strong potential biological activity Effect

Inactive Publication Date: 2011-05-25
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The innovation of the present invention lies in the synthesis of a barbituric acid derivative containing thiophene and fluorine substitution, and the synthesis method of the barbituric acid derivative, which has not yet been reported

Method used

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  • Barbituric acid derivatives and preparation method thereof
  • Barbituric acid derivatives and preparation method thereof
  • Barbituric acid derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Put 1.26g of 2-acetylthiophene, 1.36g of p-fluorobenzaldehyde, 1.56g of 1,3-dimethylbarbituric acid and 0.1g of ammonium acetate in a 50ml reaction flask and mix evenly, heat and stir, and control the temperature At 110°C, reacted for 3 hours; after the reaction was completed, the reaction mixture was dissolved with 20 ml of dichloromethane, washed twice with 2 ml of water, dried over anhydrous sodium sulfate, then evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain 3.30 g white solid 5-(1-(4-fluorophenyl)-3-oxo-3-(thiophen-2-yl)propyl)-1,3-dimethylbarbituric acid, yield 85 %.

[0024] After testing, the molecular formula of the product: C 19 h 17 FN 2 o 4 S, molecular weight: 388.41, appearance: white solid, melting point: 124-125°C.

[0025] 1 H NMR (CDCl 3 , 400MHz) δ: 7.83 (dd, 1H, J=0.8, 4.0Hz, ArH), 7.65 (dd, 1H, J=0.8, 5.2Hz, ArH), 7.15-7.08 (m, 3H, ArH), 6.98- 6.92(m, 2H, ArH), 4.38-4.34(m, 1H, CH), 4.02-3.93(m, 2H, CH), 3.49-...

Embodiment 2

[0029] 12.6g 2-acetylthiophene, 13.6g p-fluorobenzaldehyde, 15.6g 1,3-dimethylbarbituric acid and 1g ammonium acetate were placed in a 250 ml reaction flask and mixed uniformly, heated and stirred, and the temperature was controlled at 120°C, reacted for 2.5 hours; after the reaction was completed, the reaction mixture was dissolved with 200 ml of dichloromethane, washed twice with 200 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain the corresponding white Product 5-(1-(4-fluorophenyl)-3-oxo-3-(thiophen-2-yl)propyl)-1,3-dimethylbarbituric acid 33.6g, the yield is 87 %, melting point: 124-125°C.

Embodiment 3

[0031] 100.8g 2-acetylthiophene, 161.2g p-fluorobenzaldehyde, 124.8g 1,3-dimethylbarbituric acid and 10g ammonium acetate were placed in a 1000 ml reaction flask and mixed evenly, heated and stirred, and the temperature was controlled at 125°C, reacted for 2.5 hours; after the reaction was completed, the reaction mixture was dissolved with 2000 ml of dichloromethane, washed twice with 2000 ml of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and recrystallized with 95% ethanol to obtain 328 g of a white solid 5-(1-(4-Fluorophenyl)-3-oxo-3-(thien-2-yl)propyl)-1,3-dimethylbarbituric acid, 84% yield, m.p. : 124-125°C.

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Abstract

The invention provides barbituric acid derivatives and a preparation method thereof. The barbituric acid derivatives provided by the invention introduce fluorine atoms which have small radiuses and high electronegativity, and the bond energy of formed C-F bonds is higher than that of C-H bonds, thereby improving the stability and bioactivity of organic fluorine compounds; and the organic fluorine compounds have relatively higher lipid solubility and relatively higher hydrophobicity. The barbituric acid derivatives provided by the invention introduce thiophene at the same time of introducing the fluorine atoms so as to achieve higher potential bioactivity and be easier to absorb. In-vitro antibacterial tests show that the compounds have a relatively better inhibiting effect on tested bacteria, and can be further developed as antibacterial agents or leading compounds. In the preparation method provided by the invention, a solvent-free one-step synthesis method is adopted; and the preparation method has the advantages of readily-available raw materials, simple operations, environmental-friendliness, high yield and the like.

Description

technical field [0001] The invention relates to a barbituric acid derivative, in particular to a barbituric acid derivative containing thiophene and fluorine substitution and a preparation method thereof. Background technique [0002] Barbituric acid and its derivatives are nitrogen-containing heterocyclic compounds with important physiological activities. Most barbiturates have medicinal effects on the central nervous system. For example, phenobarbital and its sodium salt have hypnotic and anticonvulsant effects. It can be used to treat insomnia, epilepsy and anxiety. In addition, many barbiturates have anticancer, antibacterial, antiviral, and antioxidative activities, and have shown wide application and development prospects in medical care. Barbituric acid and its derivatives are also common intravenous general anesthetics, such as thiopental sodium is a short-acting barbiturate intravenous general anesthetics. [0003] Thiophene compounds are important sulfur-containi...

Claims

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Application Information

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IPC IPC(8): C07D409/10
Inventor 李卫林晁淑军杨丽娟闫云辉罗秋燕
Owner XINXIANG MEDICAL UNIV
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