Unlock instant, AI-driven research and patent intelligence for your innovation.

N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound and preparation method thereof

A technology of dihydropyrimidine and compounds, which is applied in the field of drug synthesis, can solve problems such as inability to insert into biomembranes, and achieve the effects of stable target products, fewer by-products, and high yields

Inactive Publication Date: 2013-09-25
HUNAN UNIV OF SCI & TECH
View PDF2 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention combines 3,4-dihydropyrimidin-2-one with C 60 Combined, the purpose is to overcome the defect that 3,4-dihydropyrimidin-2-one cannot be inserted into the biomembrane, and obtain a C that can be inserted into the biomembrane 60 antibacterial drugs

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound and preparation method thereof
  • N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound and preparation method thereof
  • N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] a. Weigh 1-(4-bromobutyl)-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-one (0.60g, 1.50mmol) in a circle In the bottom flask, add 30mL of acetone to make it completely dissolved, then add p-hydroxybenzaldehyde (1.11g, 9.00mmol) and 3.00g of anhydrous potassium carbonate, stir at room temperature for 24 hours, TLC traces the reaction is complete;

[0035] b. After the reaction is complete, the acetone in the solution is evaporated under reduced pressure, then distilled water and dichloromethane are added for extraction, the organic phase is collected, filtered, dried, and column chromatography is carried out with 200-300 mesh silica gel, and the eluent is acetic acid Ethyl ester: Petroleum ether (1:3, v / v), after precipitation and drying, white solid 1-[1-(4-formyl)phenyl]butoxy-4-phenyl-5-ethoxy Carbonyl-6-methyl-3,4-dihydropyrimidin-2-one;

[0036] c. Weigh C 60 (100mg, 0.14mmol) was added to a three-necked flask with toluene (130mL), stirred at room tem...

Embodiment 2

[0041] Repeat Example 1 with the following differences: the raw material is changed to 1-(4-bromobutyl)-4-p-methylphenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidine- 2-keto (0.60g, 1.50mmol), C 60 (150mg, 0.21mmol), the eluent was changed to ethyl acetate: petroleum ether (1:4, v / v), toluene: ethyl acetate (7:1, v / v), and 40mg of tan solid was obtained. The rate is 24.1%.

[0042] The spectral data of the product are as follows: 1 H NMR (500MHz, CDCl 3 )δ7.71(br s,2H,β-phenyl),7.13(d,J=7.5Hz,2H,DHPM-phenyl),7.08(d,J=7.5Hz,2H,DHPM-phenyl),6.93(d ,J=6.5Hz,2H,α-phenyl),5.39(br s,1H,NH,exchanged with D 2 O),5.33(br s,1H,CH),4.98(d,J=9.0Hz,1H,β-pyrrole CH 2 ),4.88(s,1H,β-pyrrole CH),4.24(d,J=9.0Hz,1H,β-pyrrole CH 2 ),4.08-4.13(m,2H,ester-CH 2 ),3.89-4.01(m,3H,NCH 2 ,OCH 2 ),3.61-3.72(m,1H,NCH 2 ),2.79(s,3H,6-CH 3 ),2.52(s,3H,N-CH 3 ),2.27(s,3H,phenyl-CH 3 ),1.67-1.85(m,4H,2×CH 2 ),1.18(t,J=6.9Hz,3H,ester-CH 3 ). 13 C NMR (126MHz, CDCl 3 )δ166.07,158.98,154.10,1...

Embodiment 3

[0045] Repeat Example 1 with the following differences: the raw material is changed to 1-(4-bromobutyl)-4-p-methoxyphenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidine -2-ketone (0.64g, 1.50mmol), C 60 (150mg, 0.21mmol), the reflux time was changed to 6 hours, the eluent was changed to ethyl acetate: petroleum ether (1:1.5, v / v), toluene: ethyl acetate (4:1, v / v), 50 mg of tan solid was obtained with a yield of 29.7%.

[0046] The spectral data of the product are as follows: 1 H NMR (500MHz, CDCl 3 )δ7.70(br s,2H,β-phenyl),7.16(d,J=8.5Hz,2H,DHPM-phenyl),6.94(d,J=7.0Hz,2H,DHPM-phenyl),6.81(d ,J=8.5Hz,2H,α-phenyl),5.36(br s,1H,NH,exchanged with D 2 O),5.31(br s,1H,CH),4.98(d,J=9.5Hz,1H,β-pyrrole CH 2 ),4.88(s,1H,β-pyrrole CH),4.24(d,J=9.0Hz,1H,β-pyrrole CH 2 ),4.08(q,J=7.0Hz,2H,ester-CH 2 ),3.94-3.97(m,3H,NCH 2 ,OCH 2 ),3.74(s,3H,phenyl-OCH 3 ),3.66-3.71(m,1H,NCH 2 ),2.79(s,3H,6-CH 3 ),2.52(s,3H,N-CH 3 ),1.68-1.82(m,4H,2×CH 2 ),1.17(t,J=7.0Hz,3H,ester-CH 3 ). 1...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the field of medicament synthesis and particularly relates to a N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound and a preparation method thereof. The preparation method comprises the following steps of: firstly utilizing N1-substituted 3,4-dihydropyrimidine-2-ketone and p-hydroxy benzaldehyde to carry out Williamson reaction and preparing N1-aromatic-aldehyde-substituted 3,4-dihydropyrimidine-2-ketone; then under the inert atmosphere, adding the N1-aromatic-aldehyde-substituted 3,4-dihydropyrimidine-2-ketone into C60 methylbenzene solution, heating and backflowing; after the reaction is finished, cooling to room temperature, separating, purifying and obtaining the N1-substituted 3,4-dihydropyrimidine-2-ketone-C60 compound. The preparation method is simple, target products are stable, the productivity is higher, the operation is simple and safe, and a new path is provided for developing antibacterial medicaments.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to an N1 substituted 3,4-dihydropyrimidin-2-one-C 60 Compounds and methods for their preparation. Background technique [0002] C 60 It is another allotrope of carbon besides diamond and graphite. Due to its special three-dimensional spherical structure and unique electron-deficient characteristics, C 60 Many surface modification reactions can occur. Among them, using imine ylide and C 60 A 1,3-dipolar cycloaddition reaction gives C 60 Derivatives, are C 60 An important method of surface functionalization with a wide range of applications. 3,4-Dihydropyrimidin-2-one derivatives have antibacterial, antiviral, antihypertensive and anticancer activities. However, the current study found that 3,4-dihydropyrimidin-2-one cannot insert into biofilms. Under the conditions of existing research, the binding probability of 3,4-dihydropyrimidin-2-one derivatives to biological target enzym...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61P31/00
Inventor 曾荣今刘传磊沈鹏飞唐沙肖高飞徐州
Owner HUNAN UNIV OF SCI & TECH