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Benzoxazepin bacteriostats and synthetic method thereof

A technology of benzoxanthine and a bacteriostatic agent is applied in the application field of active ingredients to achieve the effects of low preparation cost, high reaction efficiency and simple operation

Active Publication Date: 2017-06-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the large-scale and extensive application of antibacterial agents, the corresponding bacteria have also emerged with obvious drug resistance.

Method used

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  • Benzoxazepin bacteriostats and synthetic method thereof
  • Benzoxazepin bacteriostats and synthetic method thereof
  • Benzoxazepin bacteriostats and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A synthetic N-(tert-butyl)-2-(4-chlorophenyl)-5-oxo-3,5-dihydrobenzo[e][1,4]oxazepine-3-carboxamide method, including the following experimental steps:

[0028] Weigh o-azidobenzoic acid 1 (0.16g, 1mmol), weigh p-chloroacetophenone aldehyde 2 (0.17g, 1mmol) and tert-butylisonitrile 3 (0.08g, 1mmol) and add them to 5ml of dichloromethane, Placed at room temperature and reacted for 24 hours, azidobenzoate derivatives can be generated; the reaction solution was not separated, and triphenylphosphine (3.15g, 1.2mmol) was added, and intramolecular Wittig reaction; after the reaction is completed, the target compound 4a is obtained by column chromatography separation and purification through a silica gel column:

[0029]

[0030] Yield: 86%

[0031]

[0032] 1 HNMR (CDCl 3 ,600MHz)δ(ppm)7.98(d,J=6.6Hz,1H,Ar-H),7.76-7.69(m,3H,Ar-H),7.46-7.39(m,4H,Ar-H),6.79 (s,1H,NH),5.16(s,1H,CH),1.38(s,9H,CH 3 ).

[0033] HRMS Calculated for [C 20 h 19 ClN 2 o 3 +H]+:371.1162...

Embodiment 2

[0035] A method for synthesizing (4-bromophenyl)-N-(tert-butyl)-5-oxo-3,5-dihydrobenzo[e][1,4]oxazepine-3-carboxamide , including the following experimental steps:

[0036] Weigh o-azidobenzoic acid 1 (0.16g, 1mmol), weigh p-bromoacetophenone aldehyde 2 (0.21g, 1mmol) and tert-butylisonitrile 3 (0.08g, 1mmol) and add them to 5ml of dichloromethane, Placed at room temperature and reacted for 24 hours, azidobenzoate derivatives can be generated; the reaction solution was not separated, and triphenylphosphine (3.15g, 1.2mmol) was added, and intramolecular Wittig reaction; after the reaction is completed, the target compound 4b is obtained by column chromatography separation and purification through a silica gel column:

[0037] Yield: 83%

[0038]

[0039] 1 H NMR (CDCl 3 ,600MHz)δ(ppm)7.97(d,J=7.8Hz,1H,Ar-H),7.70-7.56(m,5H,Ar-H),7.45-7.38(m,2H,Ar-H),6.77 (s,1H,NH),5.16(s,1H,CH),1.37(s,9H,CH 3 ).

[0040] HRMS Calculated for [C 20 h 19 BrN 2 o 3 +H]+: 415.0657, Fo...

Embodiment 3

[0042] A method for synthesizing (4-chlorophenyl)-N-cyclohexyl-5-oxo-3,5-dihydrobenzo[e][1,4]oxazepine-3-carboxamide, comprising the following Experimental steps:

[0043] Weigh o-azidobenzoic acid 1 (0.16g, 1mmol), weigh p-chloroacetophenone aldehyde 2 (0.17g, 1mmol) and cyclohexylisocyanide 3 (0.11g, 1mmol) and add them to 5ml of dichloromethane , placed at room temperature and reacted for 24 hours to generate azidobenzoate derivatives; the reaction solution was not separated, and triphenylphosphine (3.15g, 1.2mmol) was added, and molecular Inner Wittig reaction; the residue was separated and purified by silica gel column chromatography to obtain the target compound 4c:

[0044] Yield: 79%

[0045]

[0046] 1 H NMR (CDCl 3 ,600MHz)δ(ppm)7.98(d,J=7.8Hz,1H,Ar-H),7.74-7.69(m,3H,Ar-H),7.46-7.40(m,4H,Ar-H),6.91 (s,1H,NH),5.24(s,1H,CH),3.79(s,1H,CH),1.97-1.74(m,4H,CH 2 ),1.34-1.17(m,6H,CH 2 ).

[0047] HRMS Calculated for [C 22 h 21 ClN 2 o3 +H]+: 397.1319, Found: ...

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Abstract

The invention relates to benzoxazepin bacteriostats and a preparation method thereof. The chemical structural formula is shown in the specification, wherein substituents R1, R2 and R3 are chloro, bromo, methyl, normal-butyl, p-chlorophenyl, methyl acetate groups, tertiary butyl or cyclohexyl, and positions, the number and conjugate positions of the substituents are not fixed. According to the synthetic method, ortho-azidobenzoic acid compounds and aryl ketoaldehyde compounds and in-situ formed isocyanide compounds are subjected toa Passerini reaction, a formed product and triphenylphosphine are subjected toa Staudinger reaction, and polysubstituted benzoxazepin heterocyclic compounds and other important heterocyclic compounds are produced through ring closing of an intramolecular aza-Wittig reaction. The key point of the invention is to provide one novel synthetic method which adopts fewer steps and has high yield to synthesize the novel benzoxazepin compounds. The compounds have better inhibitory activity on Rhizoctonia solani, Penicillium digitatum and Penicillium italicum and can be used as the bacteriostats.

Description

technical field [0001] The invention relates to a benzoxazepine derivative and its application as an active ingredient of a fungicide. Background technique [0002] The invention and application of antibacterial agents have greatly enhanced the ability of human beings to resist bacterial infections. Since the British scientist Fleming discovered penicillin in 1929, antibacterial agents have been in a vigorous development. The types of antibacterial agents have grown from the original penicillin to several thousand, and the scope of application has also expanded from humans to livestock and agricultural production. However, with the large-scale and extensive application of bacteriostatic agents, the corresponding pathogens have also emerged with obvious drug resistance. Therefore, it is particularly important to continuously research and develop new antibacterial agents to improve the ability of humans to resist diseases caused by microorganisms such as bacteria and viruses...

Claims

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Application Information

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IPC IPC(8): C07D267/14A01N43/72A01P3/00
CPCA01N43/72C07D267/14
Inventor 王龙杨键叶斯培李德江
Owner CHINA THREE GORGES UNIV
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