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P-aminobenzene sulfonic acid metal complex antibacterial agent as well as preparation method and application thereof

A technology of p-aminobenzenesulfonic acid and metal complexes, which is applied in the direction of antifungal agents, antibacterial drugs, zinc organic compounds, etc., and can solve the severe toxicity of sulfanilamide compounds, the difficulty of synthesizing sulfanilamide compounds, and the insufficient antibacterial activity of sulfanilamide compounds Strong and other problems, to achieve the effect of good inhibitory activity, good inhibitory activity, and outstanding antibacterial effect

Active Publication Date: 2018-05-11
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] ① Most of the sulfonamide compounds are highly toxic;
[0008] ② The antibacterial activity of sulfa compounds is not strong enough;
[0009] ③ Most of the sulfonamide compounds with good antibacterial effect are difficult to synthesize

Method used

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  • P-aminobenzene sulfonic acid metal complex antibacterial agent as well as preparation method and application thereof
  • P-aminobenzene sulfonic acid metal complex antibacterial agent as well as preparation method and application thereof
  • P-aminobenzene sulfonic acid metal complex antibacterial agent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesize the p-aminobenzenesulfonate titanium complex used in this embodiment as follows

[0052]

[0053] Dissolve 1.54g of 4-amino-3-methylbenzenesulfonic acid (Ⅲ) in 10mL of ethanol, and slowly add 5mL of an ethanol solution with a concentration of 0.14g / mL tetrabutyl titanate (II) dropwise at room temperature. Stir at 70°C for 3-5 hours, then cool to room temperature, remove the solvent by rotary evaporation, and the residual solid is the target product (IV). 1 H NMR (400MHz,D 2 O) δ 7.52 (s, 4H), 7.14 (dd, J = 8.2, 1.6 Hz, 4H), 6.83 (d, J = 8.2 Hz, 4H), 2.23 (s, 12H). figure 1 For the product (Ⅳ) 1 H NMR spectrum.

Embodiment 2

[0055]

[0056] Synthesize the p-aminobenzenesulfonate zinc complex used in this embodiment as follows

[0057] Dissolve 1.87g of 4-amino-3-methylbenzenesulfonic acid (Ⅲ) in 15mL of ethanol, add 400mg of NaOH solid, stir at room temperature for half an hour, add 940mg of anhydrous zinc nitrate (Ⅴ), stir at 50-70°C for 3 ~5 hours, after cooling, the solvent was distilled off under reduced pressure, and the remaining solid was the target product (Ⅵ). 1 H NMR (400MHz,D 2 O) δ 7.56 (s, 2H), 7.16 (d, J = 8.1 Hz, 2H), 6.88 (d, J = 8.1 Hz, 2H), 2.28 (s, 6H).

Embodiment 3

[0059]

[0060] Synthesize the p-aminobenzenesulfonate silver complex used in this embodiment as follows

[0061] Dissolve 2.03g of 4-amino-3-methoxybenzenesulfonic acid (Ⅷ) in 15mL of ethanol, add 123mg of silver oxide solid, stir at 60-70°C for 3-5 hours, filter after cooling, and distill off the filtrate under reduced pressure solvent, and the remaining solid is the target product (IX). 1 H NMR (400MHz,D 2 O) δ 7.54 (s, 1H), 7.08 (dd, J=8.0, 1.4Hz, 1H), 6.85 (d, J=8.0Hz, 1H), 3.75 (s, 3H).

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Abstract

The invention discloses p-aminobenzene sulfonic acid metal complexes as well as a preparation method and application thereof. Specifically, the invention solves the problems that the toxicity of sulfonamide antibacterial compounds is large, the antibacterial efficiency is not high, and the synthesis is difficult, and designs and synthesizes a series of the p-aminobenzene sulfonic acid metal complexes. The complexes provided by the invention have a short synthetic route, a simple preparation method, raw materials which are easy to obtain, good repeatability, mass production, high efficiency andlower costs. Further, the antibacterial activity of the complexes is evaluated, results show that the p-aminobenzene sulfonic acid metal complexes have excellent performance, a broad antibacterial spectrum, a prominent antibacterial effect, and low cytotoxicity compared with the current sulfonamide antibacterial compounds, and therefore the p-aminobenzene sulfonic acid metal complexes provide a high-efficiency and safe candidate medicine for clinical antibacterial treatment.

Description

technical field [0001] The invention relates to the field of antibacterial agents, in particular to a p-aminobenzenesulfonic acid metal complex antibacterial agent, its preparation method and its application in the antibacterial field. Background technique [0002] Antibacterial drugs are one of the most widely used drugs in clinical practice. They can not only reduce adverse reactions, but also improve the cure rate of diseases, reduce fatality rates, shorten the course of diseases, and achieve the purpose of reducing medical expenses. Among them, sulfonamide is the earliest chemically synthesized antibacterial drug, which plays an important role in the treatment of infectious diseases. It is currently widely used in the prevention and treatment of bacterial infections in humans and other animals. It has broad antibacterial spectrum, definite curative effect, stable properties, Advantages such as cheap price. The antibacterial mechanism of sulfonamides is to compete with p...

Claims

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Application Information

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IPC IPC(8): C07F7/28C07F3/06C07F1/10A61P31/04A61P31/10
CPCC07F1/10C07F3/06C07F7/28Y02A50/30
Inventor 喻学锋吴列李志斌王怀雨
Owner SHENZHEN INST OF ADVANCED TECH
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