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A kind of oxazolidinone compound and its preparation method and application

A technology of compound and oxazolidinone, which is applied in the field of compound and its preparation, can solve the problems such as the activity needs to be improved, and achieve the effect of improving the activity

Active Publication Date: 2016-06-08
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Linezolid is a new type of antibiotic launched in 2000. It can bind to the peptide transfer center and be used to treat diseases caused by a variety of drug-resistant bacteria, but its activity needs to be improved.

Method used

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  • A kind of oxazolidinone compound and its preparation method and application
  • A kind of oxazolidinone compound and its preparation method and application
  • A kind of oxazolidinone compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] This example is used to prepare the oxazolidinone compound provided by the present invention.

[0107] The preparation process includes the following steps:

[0108] step 1):

[0109]

[0110] Dissolve 196mg of A4, 140mg of N-hydroxysuccinimide, and 300mg of dicyclohexylcarbodiimide in 20ml of dry DMF, and stir at room temperature for 24 hours. The insoluble matter was removed by filtration, purified by silica gel column (CH 2 Cl 2 : MeOH=30:1), to obtain 130 mg of white solid (yield 45%).

[0111] L2 1 HNMR (DMSO-d 6 ,400MHz)δ(ppm)7.71and7.23(dd,J=15.4Hz,2H),2.89(s,4H),2.42(s,3H).

[0112] Step (2):

[0113]

[0114]Dissolve 34 mg Linezolid in 10 mL dry CH 2 Cl 2 , adding 38 μL boron tribromide, a white insoluble matter was formed immediately, stirred at room temperature for 24 hours, TLC detection (CH 2 Cl 2 :MeOH=20:1) about 50% of the reaction. Add 5 mL of saturated sodium bicarbonate, and add water until there is no insoluble matter. After separa...

Embodiment 2

[0125] This example is used to prepare the oxazolidinone compound provided by the present invention.

[0126] The preparation process includes the following steps:

[0127] step 1):

[0128]

[0129] Dissolve 34 mg Linezolid in 10 mL dry CH 2 Cl 2 , adding 38 μL boron tribromide, a white insoluble matter was formed immediately, stirred at room temperature for 24 hours, TLC detection (CH 2 Cl 2 :MeOH=20:1) about 50% of the reaction. Add 5 mL of saturated sodium bicarbonate, and add water until there is no insoluble matter. After separation, the aqueous phase was washed with CH 2 Cl 2 Extraction, combined organic phase, drying over anhydrous sodium sulfate, silica gel column chromatography (CH 2 Cl 2 :MeOH=30:1), to obtain 21 mg of a colorless oil (ie compound L1) (yield 50%).

[0130] L1 1 HNMR (CDCl 3 ,400MHz)δ(ppm)7.45(dd,J=2.4and14.3Hz,1H),7.10(m,2H),6.23(t,J=6.0Hz,1H),4.78(m,1H),4.03(t ,J=9.0Hz,1H),3.76(dd,J=6.8and9.1Hz,1H),3.64(m,4H),3.53(t,J=6.8Hz,2H),3.37...

Embodiment 3

[0140] This example is used to prepare the oxazolidinone compound provided by the present invention.

[0141] The preparation process includes the following steps:

[0142]

[0143] Dissolve 50mg4 in 3mL dry DMF, add 22mgDEAD and 34mg triphenylphosphine, stir at room temperature for 20 hours, purify on a silica gel column (CH 2 Cl 2 : MeOH: 25% ammonia water=15:5:0.2), obtain 40mg of white solid, productive rate 83%.

[0144] 8 1 HNMR (D 2 O,400MHz)δ(ppm)7.48(m,2H),7.20(m,2H),7.08(t,J=9.0Hz,1H),4.80(m,1H),4.13(t,J=9.0Hz, 1H),3.81(dd,J=6.7and9.5Hz,1H),3.57(m,4H),3.22(m,6H),2.97(s,4H),2.86(m,2H),2.37(s,3H ),1.98(s,3H). 13 CNMR(d 6 -DMSO, 100MHz) δ (ppm) 174.1, 170.3, 164.8, 156.6, 156.1, 151.9, 147.6, 132.7, 129.9, 122.3, 120.7, 115.5, 108.6, 108.3, 106.7, 73.5, 58.3, 54.0, 59, 43.2.2. ,30.8,22.5,17.0.HRMS(ESI):calculatedforC 26 h 32 FN 7 o 6 (M+H) + 558.2476,found:558.2473.

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Abstract

The invention discloses an oxazolidinone compound as well as a preparation method and an application thereof. The oxazolidinone compound is a compound shown as a formula (I-I), a formula (I-II) or a formula (I-III) or pharmaceutically acceptable salts thereof. According to the oxazolidinone compound as well as the preparation method and the application thereof, pseudouridine is led into one end of a molecule of a linezolid antibiotic to obviously improve the activity of the linezolid antibiotic.

Description

technical field [0001] The present invention relates to a compound and its preparation method and application, in particular to an oxazolidinone compound which can be used as protein synthesis inhibitor, its preparation method and application. Background technique [0002] Ribosome is the place where protein synthesis is carried out in organisms, and it is also a very important target of antibiotics. These antibiotics kill or inhibit the growth of bacteria by interfering with normal protein synthesis. Clinically used macrolides, aminoglycosides, chloramphenicol, tetracyclines, lincosamides, oxazolones, etc. are all antibiotics that act on ribosomes. However, with the widespread use of antibiotics, there are more and more resistant bacterial strains, and the problem of drug resistance is becoming more and more serious. It is of great significance to develop new antibiotics. [0003] Ribosomes contain two subunits, large and small, and the peptide transfer reaction center on ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C07D413/14A61K31/513A61P31/04
CPCY02A50/30
Inventor 席真李世博
Owner NANKAI UNIV