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Vancomycin derivate, and preparation method and application thereof

A technology of vancomycin and norvancomycin, applied in the direction of glycopeptide components, antibacterial drugs, peptides, etc., can solve the problems of drug resistance of various microorganisms

Inactive Publication Date: 2011-11-23
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While traditional infectious diseases have not been completely controlled, new infectious diseases and pathogens are still emerging, and the drug resistance of various microorganisms is becoming more and more serious, which has become a difficult problem in clinical treatment

Method used

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  • Vancomycin derivate, and preparation method and application thereof
  • Vancomycin derivate, and preparation method and application thereof
  • Vancomycin derivate, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1 Synthesis of fluorenylmethoxycarbonyl (Fmoc) norvancomycin

[0040]

[0041] As shown in Scheme 1, add norvancomycin hydrochloride (100mg, 0.068mmol) in a 10ml reaction tube, after dissolving with 0.5ml water and 0.5ml dioxane, add 9-fluouenylmethyl (21.10mg, 0.082 mmol), DIEA (11.65ul, 0.068mmol) was added dropwise, and reacted at room temperature for 10h. The reaction solution was subjected to RP-18 silica gel column chromatography, and the 3 OH:H 2 O=1:1→2:1 gradient elution gave Compound 3110mg with a yield of 95.2%.

Embodiment

[0042] Example Synthesis of 2N-aminocarbonyl vancomycin

[0043]

[0044] As shown in Scheme 2, vancomycin hydrochloride (90mg, 0.061mmol) was added into a 5ml reaction tube, and mixed solvent (Py:H 2 After 2ml of O=1:1) was dissolved, ethyl isocyanate (7.1ul, 0.091mmol) was added dropwise, and reacted at 30°C for 4h. The solvent was evaporated to dryness under reduced pressure, and the residue was purified by reverse-phase silica gel column chromatography with CH 3 OH:H 2 O=1:1 elution gave carboyl vancomycin (4)a 62 mg with a yield of 53%.

[0045] According to the same method, the compounds represented by (4)b-d were prepared in high yields.

Embodiment 3

[0046] Embodiment 3 Synthesis of N-aminocarbonyl norvancomycin

[0047]

[0048] As shown in Scheme 3, the compound N-Fmoc norvancomycin (100mg, 0.06mmol) was dissolved in 2ml of mixed solvent (Py:DMF=1:1), ethyl isocyanate (6.4ul, 0.09mmol) was added dropwise, React at room temperature for 5 hours, evaporate most of the solvent under reduced pressure, add 20ml of diethyl ether to precipitate a white solid, filter off the diethyl ether solution, and then wash the solid with 2*20ml of diethyl ether. The solid was dried to obtain 98.8 mg of the compound with a yield of 94.8%. Add the above solid (90mg, 0.061mmol) into a 5ml reaction tube, dissolve it with 1ml DMF, add dropwise 0.2ml of piperidine, and react at 10°C for 12h. The reaction solution was subjected to silica gel column chromatography, and CHCl 3 :CH 3 OH:H 2 O=4:4:0.7 was eluted to obtain 72 mg of compound (8)a with a yield of 91.8%.

[0049] According to the same method, the compounds represented by (8)b-d we...

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Abstract

The invention belongs to the technical fields of pharmaceutical chemistry and medicine, relates to a novel glycopeptide derivate having antibacterial activity, and particularly relates to a vancomycin derivate shown in formula (1), and a preparation method and application thereof. In-vitro antibacterial experiment shows that the compound provided by the invention has obvious antibacterial activity on multiple Gram-positive bacteria and can be used as a pharmaceutical active ingredient for preparing medicaments (especially medicaments for resisting bacterial infection).

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine, and relates to a novel glycopeptide derivative with antibacterial activity. It specifically relates to vancomycin derivatives and their preparation methods and uses. Background technique [0002] In the past half a century, antibiotics have achieved great success in the treatment of bacterial infectious diseases. However, its widespread use has also made drug-resistant pathogenic strains a very common pathogen causing clinical infections. While traditional infectious diseases have not been completely controlled, new infectious diseases and pathogens are still emerging, and the drug resistance of various microorganisms is becoming more and more serious, which has become a difficult problem in clinical treatment. Therefore, it is urgent and important to develop a new generation of antibiotics that are effective against drug-resistant strains. [0003] Vancomycin and deme...

Claims

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Application Information

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IPC IPC(8): C07K9/00A61K38/14A61P31/04
Inventor 徐亮孙逊高彬恒昌军章思及
Owner FUDAN UNIV
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