Thiouracil derivatives containing oxadiazole/thiadiazole and preparation method and application of thiouracil derivatives

A technology of thiouracil and its derivatives, which is applied in the field of thiouracil derivatives and their preparation, and can solve the problems of poor antibacterial activity due to drug resistance

Inactive Publication Date: 2015-12-16
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a class of thiouracil derivatives containing oxadiazole/thiadiazole, simultaneously provide the synthetic method of this type of derivative and the application of this type of derivative in the preparation of an

Method used

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  • Thiouracil derivatives containing oxadiazole/thiadiazole and preparation method and application of thiouracil derivatives
  • Thiouracil derivatives containing oxadiazole/thiadiazole and preparation method and application of thiouracil derivatives
  • Thiouracil derivatives containing oxadiazole/thiadiazole and preparation method and application of thiouracil derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0093] According to the concrete synthetic steps of above-mentioned general chemical formula I, when aromatic aldehyde is 2,4-dichlorobenzaldehyde in step (1), i.e. R 2 When being 2,4-dichloro, when the aromatic aldehyde in step (2) is benzaldehyde, ie R 1 When it is hydrogen, the final product compound Ia is obtained according to the above synthesis method, named as: 4-(((5-cyano-4-(2,4-dichlorophenyl)-6-oxo-1,6-dichlorophenyl) Hydropyrimidin-2-yl)thio)methyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide; its chemical structure is:

[0094]

[0095] After detection, compound Ia4-(((5-cyano-4-(2,4-dichlorophenyl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)methyl) -N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide: pale yellow solid, yield 59.6%, m.p.219.2~222.3℃; IR(KBr,cm -1 ):3393(N-H)and1642,1687(2C=O),2364(-CN); 1 HNMR (DMSO-d 6 ,600MHz)δ:8.01(d,J=7.8Hz,2H,ArH),7.76(d,J=7.2Hz,2H,ArH),7.69(d,J=8.4Hz,2H,ArH),7.64(dd ,J=7.2Hz,J=7.8Hz,2H,ArH),7.58(dd,J=7.2Hz,J=7.8Hz,2H,ArH),7.47(d,J=...

Embodiment 2

[0097] According to the concrete synthetic steps of above-mentioned general chemical formula I, when aromatic aldehyde is 2,6-dichlorobenzaldehyde in step (1), i.e. R 2 When being 2,6-dichloro, when the aromatic aldehyde in step (2) is benzaldehyde, ie R 1 When it is hydrogen, the final product compound Ib is obtained, named after: 4-(((5-cyano-4-(2,6-dichlorophenyl)-6-oxo-1,6-dihydropyrimidine-2 -yl)thio)methyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide.

[0098] After detection, compound Ib4-(((5-cyano-4-(2,6-dichlorophenyl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio)methyl) -N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide: light yellow solid, yield 56.1%, m.p.204.4~206.1℃; IR(KBr,cm -1 ):3407(N-H)and1632,1682(2C=O),2361(-CN); 1 HNMR (DMSO-d 6 ,600MHz)δ:7.96(d,J=7.8Hz,2H,ArH),7.78(d,J=7.2Hz,2H,ArH),7.66(d,J=8.4Hz,2H,ArH),7.60(dd ,J=7.2Hz,J=7.8Hz,2H,ArH),7.53(dd,J=7.2Hz,J=7.8Hz,2H,ArH),7.44(d,J=3.6Hz,1H,ArH),7.35 (d,J=6.0Hz,1H,ArH),4.40(s,2H,CH 2 ); 13 CNMR (CD 3 OD,150MHz)δ:3...

Embodiment 3

[0100] According to the specific synthetic steps of above-mentioned general chemical formula I, when aromatic aldehyde is p-phenylbenzaldehyde in step (1), i.e. R 2 When being 4-phenyl, when the aromatic aldehyde in step (2) is benzaldehyde, ie R 1 When it is hydrogen, the final product compound Ic is obtained, named as: 4-(((5-cyano-4-(1,1'-biphenyl-4-yl)-6-oxo-1,6-di Hydropyrimidin-2-yl)thio)methyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide.

[0101] After detection, compound Ic4-(((5-cyano-4-(1,1'-biphenyl-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl)thio )methyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide: light yellow solid, yield 53.6%, m.p.260.2~262.8℃; IR(KBr, cm -1 ):3409(N-H)and1632,1689(2C=O),2361(-CN); 1 HNMR (DMSO-d 6 ,600MHz)δ:8.33(d,J=7.2Hz,2H,ArH),8.02(d,J=8.4Hz,2H,ArH),7.89(d,J=8.4Hz,2H,ArH),7.77(d ,J=7.8Hz,2H,ArH),7.74(d,J=7.8Hz,2H,ArH),7.71(d,J=8.4Hz,2H,ArH),7.64(dd,J=7.2Hz,J= 7.8Hz, 2H, ArH), 7.59(dd, J=7.2Hz, J=7.8Hz, 1H, ArH), 7.50(dd, J=7.2Hz, J=8.4Hz, ...

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Abstract

The invention discloses thiouracil derivatives containing oxadiazole/thiadiazole, and further provides a method for synthesizing the thiouracil derivatives. The general chemical formula of the thiouracil derivatives is shown in figure I or figure II, wherein R1, R2 and R3 are hydrogen or halogen or aryl-. The method includes the steps of making aromatic aldehyde react with ethyl cyanoacetate and thiourea under the catalysis of piperidine to obtain a compound III, making aromatic aldehyde react with semicarbazide to obtain a compound IV, making the compound IV react with bromine to obtain a compound V, making the compound V react with benzoyl chloride to obtain a compound VI, making the compound VI and the compound III have a reflux reaction under the catalysis of potassium carbonate to obtain the general chemical formula I, making aromatic acid react with thiosemicarbazide to obtain a compound VII, making the compound VII react with benzoyl chloride to obtain a compound VIII, and making the compound VIII react with the compound III under the catalysis of potassium carbonate to obtain the general chemical formula II. The adopted method is simple, easy to operate and beneficial to large-scale production; it is verified that the prepared compound has high bacteriostatic activity and can be widely applied in bacteriostatic drug preparations.

Description

technical field [0001] The invention relates to antibacterial drugs and a preparation method thereof, in particular to a thiouracil derivative containing oxadiazole / thiadiazole, a preparation method and application thereof. Background technique [0002] Bacterial infection is the most common type of infectious disease. Without timely and effective treatment, the condition will aggravate and even cause death. Therefore, the medical community has studied various types of antibacterial drugs for clinical selection. However, with the extensive use of antibacterial drugs and antibiotics, many microorganisms have developed resistance to antibacterial drugs, and the problem of drug resistance has become one of the most difficult problems in the clinical treatment of anti-infection. Therefore, researchers in the industry need to continuously develop new antibacterial agents, especially those with new drug targets, to alleviate the problem of pathogenic bacteria's resistance to anti...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D417/12A61K31/506A61P31/04
CPCC07D413/12C07D417/12
Inventor 李小六崔朋雷陈华王炳和
Owner HEBEI UNIVERSITY
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