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Sulfonamide derivative as well as preparation method and application thereof

A technology of derivatives and sulfonamides, applied in the field of sulfonamide derivatives and their preparation

Inactive Publication Date: 2019-04-26
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] In recent years, with the widespread use and abuse of antibacterial drugs in clinical practice, drug resistance has become a difficult global problem. Many patients with bacterial infections are facing a situation where there is no cure. bring unprecedented challenges

Method used

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  • Sulfonamide derivative as well as preparation method and application thereof
  • Sulfonamide derivative as well as preparation method and application thereof
  • Sulfonamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of N-[(diethoxyphosphono)-benzyl]-benzenesulfonamide (IIa):

[0026] Weigh 1.0mmol of intermediate 1 (diethyl α-aminobenzylphosphonate) and 1.0mmol of benzenesulfonyl chloride in a 50mL reaction flask, then add 10mL of dichloromethane and 0.5mmol of basic ionic liquid [Bmim]OH, Heated to reflux, TLC monitored the reaction, after 3 hours of reaction, the solvent was concentrated by a rotary evaporator, separated and purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:2), and a white solid was obtained, which was the target compound (Ⅱa). Yield 80.6%. compound 1 H NMR, 13 C NMR and MS: 1 H-NMR (400MHz, CDCl 3 )δ:6.98-7.72(m,11H,ArH+NH),4.78-4.87(q,1H,J=36.0Hz,PCH),4.25-4.28(m,2H,OCH 2 ),3.78-3.84(m,1H,OCH 2 ),3.49-3.57(m,1H,OCH 2 ),1.34(t,3H,J=16.0Hz,CH 3 ),0.98(t,3H,J=12.0Hz,CH 3 ). 13 C-NMR (100MHz, CDCl 3 )δ: 16.0, 16.4, 55.0, 63.6, 64.1, 126.4, 127.1, 127.2, 127.4, 127.5, 128.3, 128.6, 129.0, 129.1, 132.3, 135.6, 138.1. ES...

example 1

[0027] The above example 1, if according to the following method:

[0028] Weigh 1.0mmol of intermediate 1 (diethyl α-aminobenzylphosphonate) and 1.0mmol of benzenesulfonyl chloride in a 50mL reaction flask, then add 10mL of dichloromethane and 1.0mmol of triethylamine, heat to reflux, and monitor by TLC After 13 hours of reaction, the solvent was concentrated by a rotary evaporator, separated and purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:2), and a white solid was obtained, which was the target compound (IIa), with a yield of 39.5%.

Embodiment 2

[0030] Preparation of N-[(diethoxyphosphono)-benzyl]-2-thiophenesulfonamide (Ⅱb)

[0031] Weigh 1.0mmol intermediate 1 (diethyl α-aminobenzylphosphonate) and 1.0mmol thiophene-2-sulfonyl chloride in a 50mL reaction flask, then add 10mL dichloromethane and 0.5mmol basic ionic liquid [Bmim ]OH, heated to reflux, and TLC monitored the reaction. After completion, the solvent was concentrated by a rotary evaporator, separated and purified by column chromatography (eluent was ethyl acetate:petroleum ether=1:2), and a white solid was obtained, which was the target compound (Ⅱb). , yield 84.3%. compound 1 H NMR, 13 C NMR and MS: 1 H-NMR (400MHz, CDCl 3 )δ: 7.46-7.53 (m, 1H, NH), 6.67-7.28 (m, 8H, ArH), 4.72-4.80 (q, 1H, J = 32.0Hz, PCH), 4.22-4.29 (m, 2H, OCH 2 ),3.81-3.87(m,1H,OCH 2 ),3.52-3.62(m,1H,OCH 2 ),1.33(t,3H,J=16.0Hz,CH 3 ),0.99(t,3H,J=16.0Hz,CH 3 ). 13 C-NMR (100MHz, CDCl 3 )δ: 16.0, 16.4, 54.7, 63.7, 64.0, 126.7, 127.9, 128.0, 128.1, 128.2, 131.3, 132.0, 133.3, ...

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Abstract

The invention discloses a sulfonamide derivative in the field of antibacterial compounds. The sulfonamide derivative has a structural formula as shown in formula II: (as shown in the specification); and the preparation method comprises the following steps: feeding and mixing sulfonyl chloride, an intermediate I and [Bmim]OH ionic liquid at a molar ratio of 1 to 1 to 0.5; then, adding anhydrous dichloromethane to obtain a mixture, wherein the dosage of anhydrous dichloromethane is that 10-15 mL of anhydrous dichloromethane is added into per 1 mmol of sulfonyl chloride; heating and refluxing for3-4 h after stirring the mixture uniformly; concentrating under reduced pressure to obtain a coarse product after refluxing; separating and purifying the coarse product with column chromatography toobtain a target product sulfonamide derivative II. The sulfonamide derivative II designed and synthesized in the invention has an excellent antibacterial effect against Gram-negative bacteria and Gram-positive bacteria, and particularly has significant antibacterial activity against S. aureus, E. coli, MRSA and MREC.

Description

technical field [0001] The invention belongs to the field of antibacterial compounds, and in particular relates to a sulfonamide derivative and its preparation method and application. Background technique [0002] In recent years, with the widespread use and abuse of antibacterial drugs in clinical practice, drug resistance has become a difficult global problem. Many patients with bacterial infections are facing a situation where there is no cure. bring unprecedented challenges. Therefore, it is imminent to develop novel antibacterial drugs. [0003] Since the German scientist Domagk discovered in 1932 that the sulfonamide dye Baituozi has a therapeutic effect on bacterial infections in experimental animals, the research on this type of drug has developed rapidly, and then a variety of sulfonamide antibacterial drugs have been used in clinical practice. As the earliest synthetic antibacterial drug, the discovery, application, and clarification of the mechanism of sulfonami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40A61K31/662A61P31/02A61P31/04
CPCA61P31/02A61P31/04C07F9/4043Y02A50/30
Inventor 杨家强邓玲雷延燕安家丽
Owner ZUNYI MEDICAL UNIVERSITY
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