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A class of vancomycin derivatives, its preparation method and its application in antibacterial

A technology for drugs and compounds, applied in the field of preparation of vancomycin derivatives, can solve the problems of loss of cell viability, increase of membrane permeability, etc.

Active Publication Date: 2020-05-01
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, due to the long-chain hydrophobic groups connected to vancomycin, the drug can directly act on the plasma membrane of bacteria, resulting in depolarization of the membrane potential and increased membrane permeability, resulting in loss of cell viability

Method used

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  • A class of vancomycin derivatives, its preparation method and its application in antibacterial
  • A class of vancomycin derivatives, its preparation method and its application in antibacterial
  • A class of vancomycin derivatives, its preparation method and its application in antibacterial

Examples

Experimental program
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Effect test

preparation example 1

[0132] Synthetic route of preparation example 1 intermediate 2b

[0133]

[0134] Preparation of the first step 3-hexylmercaptopropionic acid 2d

[0135] 3-Mercaptopropionic acid (2.65 g, 25 mmol) was added to the reaction flask, ethanol (25 mL) was added, 25 mL of 2M NaOH solution was added and stirred at room temperature for 5 min, and then 1-bromo-n-hexane (3.31 g, 20 mmol) TBAB (0.21 mL) was added. g, 0.65 mmol) was added, reacted at room temperature for 12 h, evaporated the ethanol under reduced pressure, adjusted the pH of the solution to 2-3 with 3M HCl solution, extracted with dichloromethane (25 mL×2), combined the organic phases, and added saturated common salt. Washed with water (35 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain Intermediate 2d, 3.62 g of a colorless oily liquid, with a yield of 94.71%.

[0136] Preparation of the second step 3-hexylsulfonylpropionic acid 2e

[0137] Dissolve 3-hexylmercaptoprop...

preparation example 2

[0140] Synthetic route of preparation example 2 intermediate 3b

[0141]

[0142] Preparation of the first step 3-heptylmercaptopropionic acid 3d

[0143] 3-Mercaptopropionic acid (2.65g, 25mmol) was added to the reaction flask, ethanol (25mL) was added, 25mL of 2M NaOH solution was added and stirred at room temperature for 5min, and then 1-bromo-n-heptane (3.58g, 20mmol) TBAB ( 0.21g, 0.65mmol) was added, reacted at room temperature for 12h, ethanol was evaporated under reduced pressure, the pH of the solution was adjusted to 2~3 with 3M HCl solution, extracted with dichloromethane (25mL×2), the organic phases were combined and saturated with Washed with brine (35 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain Intermediate 3d, 3.28 g of colorless oily liquid, with a yield of 80.26%.

[0144] Preparation of the second step 3-heptylsulfonylpropionic acid 3e

[0145] 3-heptyl mercaptopropionic acid 3d (3.28 g, 16.05 mmol) wa...

preparation example 3

[0148] Synthetic route of preparation example 3 intermediate 4b

[0149] The preparation of the first step 3-octylmercaptopropionic acid 4d

[0150] 3-Mercaptopropionic acid (2.65g, 25mmol) was added to the reaction flask, ethanol (25mL) was added, 25mL of 2M NaOH solution was added and stirred at room temperature for 5min, and then 1-bromo-n-octane (3.86g, 20mmol) TBAB ( 0.21g, 0.65mmol) was added, reacted at room temperature for 12h, ethanol was evaporated under reduced pressure, the pH of the solution was adjusted to 2~3 with 3M HCl solution, extracted with dichloromethane (25mL×2), the organic phases were combined and saturated with Washed with brine (35 mL×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain Intermediate 4d, 1.33 g of a colorless oily liquid, with a yield of 30.46%.

[0151] Preparation of the second step 3-octylsulfonylpropionic acid 4e

[0152] 3-Octylmercaptopropionic acid 4d (1.32g, 6.05mmol) was dissolved in...

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Abstract

The invention relates to a vancomycin derivative as shown in the formula (I) and a stereisomer, pharmaceutically acceptable salts, a preparation method of the vancomycin derivative and its application in treating and / or preventing diseases or symptoms related to gram negative bacterial infections.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine. It relates to novel vancomycin derivatives represented by general formula (I), and pharmaceutically acceptable salts and isomers thereof, as well as methods for preparing vancomycin derivatives and their use in the treatment and / or prevention and Gram The application of positive bacterial infection related to diseases or conditions. Background technique [0002] Bacterial infection is a disease that seriously threatens human health. Gram-positive bacterial infection is a common and frequently-occurring disease. Now there are a variety of therapeutic drugs for clinical selection, such as cephalosporins, penicillin, etc. But when human infection with Gram-positive bacteria (such as Staphylococcus and Enterococcus) is life-threatening, vancomycin is the last line of defense in clinical treatment of bacterial infection, and plays a huge role in eliminating bacterial infectio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K9/00A61K38/14A61P31/04
Inventor 冯文化贺娜
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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