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FtsZ and QseC double-target antibacterial molecule as well as preparation method and application thereof

A dual-target, molecular technology, applied in the directions of antibacterial drugs, sulfonic acid amide preparation, chemical instruments and methods, etc., can solve the problems of difficult design, synthesis and application of antibacterial molecules

Active Publication Date: 2021-05-28
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, designing effective QseC inhibitor molecules and covalently linking with corresponding FtsZ inhibitor molecules to obtain FtsZ and QseC dual-target antibacterial molecules is still a difficult problem in the design, synthesis and application of antibacterial molecules.

Method used

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  • FtsZ and QseC double-target antibacterial molecule as well as preparation method and application thereof
  • FtsZ and QseC double-target antibacterial molecule as well as preparation method and application thereof
  • FtsZ and QseC double-target antibacterial molecule as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0074]Example 1 BCA-NCS5-OH (equation 2)

[0075]

[0076]1. Synthesis of 4- (3,4,5-trichlorophenyl) benzenesulfonamide (NCS-5) (3,4,5-trichlorophenyl) benzenesulfonamide (NCS-5)figure 1 )

[0077]1) Weigh 3,4,5-trichloride 196 mg (1.0 mmol) and 233 mg (1.0 mmol) of acetaminylsylsulfonyl chloride in a 20 ml round bottom flask, and dissolved by adding 2.5 ml of dichloromethane;

[0078]2) Add 0.19 ml of triethylamine in the round bottom flask, stirring under ice water bath to 0 ° C for reaction, and then transferred to room temperature after 20 ° C for 20-30 minutes (continued to stir);

[0079]3) Room temperature for 20-30 minutes, TLC monitored reaction, 15 ml of distilled water is added to the reaction;

[0080]4) EtOAc (EtOAc) EtOAc, mixed brine, dried over an organic layer, dried over a saturated brine, filtration, filtration, and evaporative pressure reduction (-0.1MPa), the resulting solid crude product purified, The eluent is dichloromethane: methanol = 95: 5 to give brown yellow solid product...

example 2

[0102]Example 2 BCA-NCS5 (formula 3)

[0103]

[0104]1) 11.7 mg of 4-isothiocyanate-N- (3,4,5-trichlorophenyl) benzenesulfonamide (0.03 mmol) and 6.8 mg of amino α-brominnamol (0.03 mmol) 25 ml round bottom flask, and dissolved with 3 ml of dichloromethane added;

[0105]2) The reaction was stirred overnight under room temperature, filtered, evaporated. (-0.1MPa), the resulting solid crude product was purified by silica gel column: EtOAc (EtOAc) -OH (yellow oil, 5.5 mg, yield 30%);

[0106]3) Place 22 mg of BCA-NCS5-OH in a 25 ml round bottom flask, and dissolved with an additional 3.5 ml anhydrous acemitrile;

[0107]4) Add 650 mg of active manganese dioxide to the round bottom flask, stirred at room temperature for 30 minutes, thin layer chromatography;

[0108]5) After the reaction is completed, filter the core funnel, remove manganese dioxide, and the filtrate is subjected to rotation (-0.1MPa), the resulting solid crude product is purified, the eluent is n-hexane: ethyl acetate = 80: 20 The yel...

example 3

[0109]Example 3 MCA-NCS5-OH and MCA-NCS5

[0110]Molecular structure

[0111]1) MCA-NCS5-OH ((e) -4- (3- (4- (3-Hydroxy-2-MethylProp-1-EN-1-YL) Phenyl) Thioureido) -N- (3, 4, 5 -TRICHLOPHENYL) Benzenesulfonamide; Formula 4)

[0112]

[0113]2) MCA-NCS5 ((E) -4- (3- (2-methyl-3-OXOPROP-1-En-1-YL) Phenyl) Thioureido) -N- (3, 4, 5-Trichlorophenyl ) Benzenesulfonamide; formula 5)

[0114]

[0115]2. Raw materials

[0116]1) NCS-5 (4-Isothiocyanato-N- (3, 4, 5-Trichlorophenyl) Benzenesulfonamide; Formula 6), synthesisfigure 1 .

[0117]

[0118]2) See the synthesis of amino alpha-methyl licking alcoholimage 3 .

[0119](3) FTSZ and Qsec dual target molecular antibacterial activity experiment

[0120]The present invention determines the minimum inhibitory concentration (MIC) of the synthesized FTSZ and Qsec dual target molecules, detecting the effect of the FTSZ and Qsec dual-target molecules on the expression level of FTSZ protein GTPase activity and bacterial virulence factor, and then evaluation Its application in ant...

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Abstract

The invention discloses an FtsZ and QseC double-target antibacterial molecule as well as a preparation method and application thereof. The structure of the antibacterial molecule is shown as a formula 1 defined in the description, wherein R1 is H, F, Cl, Br or I; and R2 is CH2OH and CHO. According to the invention, the bacterial infection resistance effect of the antibacterial molecule is evaluated through the in vitro antibacterial activity experiment, and the result shows that the antibacterial molecule can effectively kill Gram-positive pathogenic bacteria, can reduce the toxicity of Gram-negative pathogenic bacteria, and can be used for preparing bacterial infection resistance and other related drugs.

Description

Technical field[0001]The present invention belongs to the sect of pharmaceutical field, involving FTSZ and Qsec dual-target antibacterial molecules and preparation methods thereof, and the use of antibacterial molecules in the preparation of anti-bacterial infections.Background technique[0002]The emergence of drug-resistant pathogenic bacteria makes bacterial infectious diseases seriously threaten life and health. Clinical common pathogenic bacteria have a different degree of drug resistance to most first-line antibacterial drugs, and effective antibacterial drugs are increasingly reduced. These antibacterial drugs are mostly single targets, and most of the antibacterial strategies are surrounded by traditional targets such as bacterial cell walls, proteins, nucleic acids, and modifications on the existing molecular structure, which is easy to induce bacteria to produce resistance.[0003]In order to avoid the production of bacterial resistance, two antibacterial research strategies h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/18C07C335/16C07C303/38C07C311/46C07C303/40C07C311/44C07C201/08C07C205/44C07C201/12C07C205/26C07C213/02C07C215/68C07C205/19C07C331/28A61P31/04
CPCC07C335/18C07C335/16C07C303/38C07C303/40C07C201/08C07C201/12C07C213/02C07C331/28A61P31/04C07C311/46C07C311/44C07C205/44C07C205/26C07C215/68C07C205/19Y02A50/30
Inventor 侯征王明智方超秦向阳马波薛小燕李明凯
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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