Synthetic method of QseC ligand derivatives with role of inhibiting bacterial virulence
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A technology for inhibiting bacteria and derivatives, applied in antibacterial drugs, organic chemistry, etc., can solve the problems of high toxicity of compounds, poor water solubility, and limitations in clinical application, and achieve the effect of good reproducibility and simplified operation process
Inactive Publication Date: 2010-10-13
FOURTH MILITARY MEDICAL UNIVERSITY
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It has been found that the LED209 series of compounds used for screening QseC ligands have high toxicity and poor water solubility, and are all polyheterocyclic connection products (Table 1), and have not yet been optimized and modified based on the structure of LED209 itself; At the same time, the screened compound LED209, because its sp
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Embodiment 1
[0049] Example 1 Preparation of N-(4-(N-phenylsulfamoyl) phenyl) acetamide
[0050] Add p-acetamidobenzenesulfonyl chloride (55g, 236mmol) in batches to a solution of sodium acetate (48.4g, 590mmol) and p-phenylenediamine (22mL, 200mmol) in ethanol (300mL) at 0°C, and stir overnight at room temperature The reactant was poured into ice water (1.5 L) and stirred vigorously for 1 h, and the precipitated white solid was collected by filtration, washed with ice water, dried in vacuo, and recrystallized from hot ethanol to obtain a white solid N-(4-(N-phenylsulfamoyl ) phenyl) acetamide (38 g, 60%);
Embodiment 2
[0051] Example 2 Preparation of 4-aminobenzenesulfonylanilide
[0052] Add anhydrous hydrochloric acid (6N, 40mL) to a solution of ethanol (80mL) in N-(4-(N-phenylsulfamoyl)phenyl)acetamide (20g, 55mmol) under stirring, heat to reflux for 3h, and decompress The reaction mixture was evaporated to dryness, the residue was dissolved in water, the pH value of the solution was adjusted to 8-9 with 1N ammonia water, stirred for 1 h, the precipitated white solid was collected by filtration, washed with ice water, dried in vacuum, recrystallized from hot ethanol to obtain a white solid 4 - Sulfonanilide (10 g, 65%).
Embodiment 3
[0053] Example 3 Preparation of N-phenyl-4-(3-phenylthioureido)benzenesulfonamide (i.e. compound 1)
[0054] Triethylamine (0.07 mL, 0.5 mmol) and phenylisothiocyanate (Ph-NCS, 2.1 mL, 11 mmol) were added to a solution of 4-aminobenzenesulfonanilide (2.48 g, 10 mmol) in dry acetone (30 mL) respectively , heated to reflux for 24 h, removed volatile substances in vacuum, and separated by flash silica gel column chromatography (n-hexane: acetone = 4: 1) to obtain white solid N-phenyl-4-(3-phenylthioureido)benzenesulfonate amides.
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Abstract
The invention discloses a synthetic method of QseC ligand derivatives capable of inhibiting bacterial virulence and an application. The QseC ligand derivatives are bacterial membrane surface protein QseC ligands and can be specifically combined with the QseC ligands and be used for retroregulation of a qseC-qseB-fliC-flhD gene pathway, thereby inhibiting the release of bacterial pathogenic virulence factors, reducing the bacterial virulence and the invasiveness during the bacterial infection and further achieving the role of controlling the harm of the bacterial infection; however, the QseC ligand derivatives do not affect normal growth and reproduction of bacteria, thereby avoiding the initiation of bacterial drug resistance pressure. The QseC ligand derivatives have the advantages of good anti-bacterial effect, low toxicity, good stability and difficult drug resistance. The QseC ligand derivatives synthesized by the optimized synthetic method of the QseC ligands and the chemical synthetic method of the derivatives thereof can be used for preparing novel broad-spectrum antibacterial drugs with resistance to multi-drug-resistant bacteria infection.
Description
technical field [0001] The invention relates to a synthesis method and application of a novel broad-spectrum antibacterial virulence compound QseC ligand derivative derivative, in particular to a synthesis method of the QseC ligand derivative. Background technique [0002] The quorum sensing system (QSS) is an information transmission system between bacteria. The system is capable of synthesizing and secreting autoinducer molecules (autoinducer, AI). AI reaches the outside of the cell through the diffusion or transport system. When the concentration of AI reaches a certain threshold with the density of the bacterial population, it can be recognized by the sensor protein located on the membrane and sense it. The cell density of the population ultimately initiates the expression of a specific target gene, and its expression product enables bacteria to adapt to various changes in the external environment. QSS is the most basic and necessary functional system for Gram-negative ...
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