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Disulfide bond compound as well as preparation method and antibacterial application thereof

A compound and disulfide bond technology, applied in the field of disulfide bond compounds and their preparation methods and antibacterial applications, can solve the problems of lack of chemical agents, enhanced microbial resistance, etc., and achieve good antifungal and bacterial effects active effect

Pending Publication Date: 2022-07-22
GAUNGXI TIANYUAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the shortage of chemical agents, and the abuse of traditional fungicides, microbial resistance has increased, so there is an urgent need to develop and innovate other highly effective fungicides

Method used

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  • Disulfide bond compound as well as preparation method and antibacterial application thereof
  • Disulfide bond compound as well as preparation method and antibacterial application thereof
  • Disulfide bond compound as well as preparation method and antibacterial application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of compound S1

[0039] (1) The structural formula of compound S1 is as follows:

[0040]

[0041] (2) the synthetic reaction formula of compound S1 is as follows:

[0042]

[0043] (3) the preparation method of compound S1 is as follows:

[0044] 2-Mercaptopyridine (1 mmol) and n-butanethiol (1.5 mmol) were dissolved in 10 mL of dichloromethane (DCM) at 0°C. 1 mmol of dichlorodicyanobenzoquinone (DDQ) was then slowly added to the solution in portions and the reaction mixture was stirred in an ice bath for 1 h. The progress of the reaction was monitored by thin layer chromatography. Upon completion, the solvent was removed by rotary evaporation and the crude compound was purified by column chromatography (ethyl acetate:petroleum ether, 1:50) to give the desired product S1.

[0045] (4) Results:

[0046] The obtained compound S1 is a colorless oily liquid, yield: 82%; 1 H NMR (400MHz, Chloroform-d) δ: 8.52-8.40 (m, 1H), 7.80-7.55 (...

Embodiment 2

[0047] Embodiment 2: the synthesis of compound S2

[0048] (1) The structural formula of compound S2 is as follows:

[0049]

[0050] (2) the preparation method of compound S2 is as follows:

[0051] The difference between the preparation method and Example 1 is that only n-propanethiol is used to replace the n-butanethiol of Example 1, and the others are the same as those of Example 1.

[0052] (3) Results:

[0053] The obtained compound S2 is a colorless oily liquid, yield: 85%; 1 H NMR (400MHz, Chloroform-d)δ: 8.47-8.42(m,1H), 7.75-7.70(m,1H), 7.66-7.60(m,1H), 7.08-7.03(m,1H), 2.76(t) , J=7.3Hz, 2H), 1.71(h, J=7.3Hz, 2H), 0.98(t, J=7.4Hz, 3H). 13 C NMR (100MHz, Chloroform-d) δ: 160.85, 149.65, 137.03, 120.55, 119.65, 41.09, 22.42, 13.21. MS-ESI m / z: C 8 H 11 NS 2 [M+H] + : 186.3030.

Embodiment 3

[0054] Embodiment 3: the synthesis of compound S3

[0055] (1) the structural formula of compound S3 is as follows:

[0056]

[0057] (2) the preparation method of compound S3 is as follows:

[0058] The difference between the preparation method and Example 1 is that only 2-mercaptopyrimidine is used to replace the 2-mercaptopyridine of Example 1, and n-propanethiol is used to replace the n-butanethiol of Example 1. Others are the same as those of Example 1.

[0059] (3) Results:

[0060] The obtained compound S3 is a colorless oily liquid, yield: 77%; 1 H NMR (400MHz, Chloroform-d) δ: 8.60 (d, J=4.8Hz, 2H), 7.07 (t, J=4.8Hz, 1H), 2.83 (t, J=7.3Hz, 2H), 1.73 (h) , J=7.3Hz, 2H), 0.99(t, J=7.3Hz, 3H). 13 C NMR (100MHz, Chloroform-d) δ: 172.16, 157.92, 117.89, 40.68, 22.21, 13.22. MS-ESI m / z: C 7 H 10 N 2 S 2 [M+H] + : 187.2910.

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Abstract

The invention relates to the field of medicinal chemistry, and discloses a disulfide bond compound as well as a preparation method and an antibacterial application thereof. The compound has a synergistic effect on sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum, rice blast, phytophthora capsici, aspergillus flavus, penicillium expansum, brown rot of stone fruits, root rot of stolonifer, xanthomonas oryzae, xanthomonas citri, phytophthora parasitica, escherichia coli, staphylococcus aureus, candida albicans and bacillus cereus. The compound shows potential inhibitory activity on salmonella enteritidis, listeria monocytogenes and salmonella enteritidis, and part of the compound has high inhibitory activity. The disulfide bond compound is simple to prepare, raw materials are cheap and easy to obtain, and the disulfide bond compound can be developed into a green, pollution-free and sustainable novel bacteriostatic agent.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a disulfide bond compound, a preparation method thereof, and an antibacterial application. Background technique [0002] Microorganisms usually include microorganisms with cellular structures such as bacteria, fungi, and actinomycetes, as well as organisms without complete cellular structures such as viruses, mycoplasma, and chlamydia. Most microorganisms are harmless to the human body, but some microorganisms can cause a variety of human, animal and plant diseases. For example, plant pathogens are the main cause of crop losses and bring huge economic losses. Escherichia coli and Staphylococcus aureus can cause gastrointestinal infections, urinary tract infections and other diseases in humans and animals. At present, the diseases caused by these microorganisms are mainly based on chemical fungicides. However, due to the lack of chemical agents and the abuse of traditional fungi...

Claims

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Application Information

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IPC IPC(8): C07D213/71C07D239/38C07D215/36C07D277/78C07D277/36C07D333/34A01N43/10A01N43/78A01N43/42A01N43/54A01N43/40A01P3/00A01P1/00A61P31/04A61P31/10
CPCC07D213/71C07D239/38C07D215/36C07D277/78C07D277/36C07D333/34A01N43/10A01N43/78A01N43/42A01N43/54A01N43/40A61P31/04A61P31/10
Inventor 刘映前李卫国王璟汝零春华张智军安俊霞马越
Owner GAUNGXI TIANYUAN BIOCHEM
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