Borneol derivative antibacterial agent and preparation method and application thereof

A technology of derivatives and antibacterial agents, which is applied in the field of synthetic pharmaceutical small molecules, can solve the problems of bacterial multidrug resistance, reduced curative effect, and ineffectiveness, and achieve the effects of good biocompatibility, great development potential, and strong antibacterial activity

Active Publication Date: 2019-10-22
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Antibiotics play a vital role in the treatment and control of microbial infections, but with the continuous use of antibiotics, the phenomenon of bacterial multidrug resistance is becoming more and more serious, which makes many conventional antibiotics less effective or ineffective against bacterial infections

Method used

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  • Borneol derivative antibacterial agent and preparation method and application thereof
  • Borneol derivative antibacterial agent and preparation method and application thereof
  • Borneol derivative antibacterial agent and preparation method and application thereof

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Experimental program
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Embodiment approach

[0037] As mentioned above, bacterial infection has always been a concern, and antibiotics play a vital role in the treatment and control of microbial infections. This makes many conventional antibiotics less effective or ineffective against bacterial infections. In view of this, the present inventors have conducted a lot of research on antibacterial and bactericidal substances.

[0038] The inventors noticed borneol, and designed to prepare an antibacterial small molecule substance based on borneol.

[0039] Borneol, also known as borneol, has a structural formula as shown in formula (II), is a dicyclic monoterpene alcohol widely present in plants, and has a wide range of clinical and medical values, such as analgesic, antiseptic, and sedative. Borneo is almost non-toxic to the human body, and it is also a very good penetration enhancer. It has the physiological function of loosening the cell wall or increasing its permeability. It can help some drugs penetrate various physio...

Embodiment 1

[0077] In the present embodiment, the preparation flow diagram of the antibacterial small molecular substance with molecular structure as shown in formula (I) is as follows figure 1 shown.

[0078] Weigh 1.6mmol of 4-formylbenzoic acid into a reaction flask, and add 30mL of tetrahydrofuran to provide a solvent environment. Then, add 0.2mmol DMAP and 2.0mmol DCC to the solvent in sequence. After completely dissolving, add 1mmol borneol to the above system, and continue the reaction at 30°C for 24h. Suction filtration, sedimentation and purification in a large amount of petroleum ether for 2 times, and finally through column chromatography (petroleum ether: ethyl acetate = 10:1 (v / v)) and post-processing steps such as vacuum drying to obtain the target product 4-aldehyde group The pure product of bornyl benzoate (BF) has a yield of 95%. The reaction has the advantages of mild conditions and simple operation.

[0079] Adopt Fourier Transform Infrared Spectrometer (Thermo Fishe...

Embodiment 2

[0082]Weigh 1.6mmol of 4-formylbenzoic acid into a reaction flask, and add 30mL of tetrahydrofuran to provide a solvent environment. Then, add 0.2mmol DMAP and 2.0mmol DCC to the solvent in sequence. After completely dissolving, add 1mmol borneol to the above system, and continue the reaction at 25°C for 24h. Suction filtration, sedimentation and purification in a large amount of petroleum ether for 2 times, and finally through column chromatography (petroleum ether: ethyl acetate = 10:1 (v / v)) and post-processing steps such as vacuum drying to obtain the target product 4-aldehyde group The pure product of bornyl benzoate (BF) has a yield of 88%. The reaction has the advantages of mild conditions and simple operation.

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Abstract

The invention relates to a 4-borneol aldehyde benzoate, a preparation method thereof and an antibacterial application, The 4- borneol aldehyde benzoate takes borneol and 4-aldehyde benzoic acid as rawmaterials to form a borneol esterified derivative as an antibacterial microbial substance by a one-step esterification reaction. The 4-borneol aldehyde benzoate has strong antibacterial effect on gram-positive bacteria (such as Staphylococcus aureus, Bacillus subtilis) and gram-negative bacteria (such as pseudomonas aeruginosa, acinetobacter baumannii), and has good biocompatibility and non-toxicity. In addition, the raw materials and reagents of the invention are easy to obtain, the preparation method is simple, and the products have broad application prospects in the fields of medicine, food, health and the like.

Description

technical field [0001] The invention belongs to the technical field of synthetic medicine small molecules, and relates to a borneol derivative antibacterial agent and a preparation method and application thereof. Background technique [0002] Bacterial infections have always been a concern but have troubled the healthcare industry due to their rapid spread and development. Antibiotics play a vital role in the treatment and control of microbial infections, but with the continuous use of antibiotics, the phenomenon of bacterial multidrug resistance is becoming more and more serious, which makes many conventional antibiotics less effective or ineffective against bacterial infections. Therefore, it is particularly urgent to develop effective treatment options or new antibacterial agents. Contents of the invention [0003] One of the purposes of the present invention is to provide a kind of borneol derivative antimicrobial small molecular substance for the problems existing in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/235A61P31/04A01N37/42A01P1/00C07C67/08C07C69/76
CPCA61K31/235A61P31/04A01N37/42C07C67/08C07C2602/42C07C69/76Y02A50/30
Inventor 王兴付雅南
Owner BEIJING UNIV OF CHEM TECH
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