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Glycolipid derivative based on Kdo as well as preparation and antibacterial application of glycolipid derivative

A technology of derivatives and glycolipids, which is applied in the field of synthesis of glycolipids to achieve the effects of improving the ability to penetrate the membrane and having a good inhibitory effect.

Active Publication Date: 2021-04-20
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But even compounds that have inhibitory activity on enzymes may not necessarily be able to inhibit the growth of bacteria (J.Med.Chem.1989,32,1069-1074.)

Method used

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  • Glycolipid derivative based on Kdo as well as preparation and antibacterial application of glycolipid derivative
  • Glycolipid derivative based on Kdo as well as preparation and antibacterial application of glycolipid derivative
  • Glycolipid derivative based on Kdo as well as preparation and antibacterial application of glycolipid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1. Dissolve 100 mg (0.36 mmol) of compound 1 in 1 mL of methanol, add 3.6 mL of 0.5 mol / L lithium hydroxide aqueous solution dropwise to it under stirring at room temperature, and stir the resulting mixture at room temperature for 2 h, then neutralize it with an acidic ion exchange resin To neutrality, it was filtered and concentrated to obtain compound 2 (87mg, 0.36mmol, yield 100%), and the obtained crude product was directly used in subsequent reactions.

[0037]

[0038] 2. 87 mg (0.36 mmol) of compound 2 and 116 mg (0.43 mmol) of stearylamine were dissolved in 4 mL of DMF, and 89 mg (0.46 mmol) of EDCI, 63 mg (0.47 mmol) of HOBt and 108 μL ( 0.62mmol) DIPEA, stirred at room temperature for 8.5h, concentrated to remove the solvent, and the resulting syrup was dissolved in CH 2 Cl 2after dissolving with H 2 Washed with O, the organic phase was collected and washed with Na 2 SO 4 Drying, filtration and concentration, column chromatography (CH 2 Cl 2 / MeOH=10:...

Embodiment 2

[0045] 1. Dissolve 200 mg (0.73 mmol) of compound 1 in 7 mL of a mixed solution of tetrahydrofuran and deionized water at a volume ratio of 6:1, and add 526 mg (1.78 mmol) of triphenylphosphine, and heat the resulting mixture to 60°C for 7 hours; After the reaction solution was cooled to room temperature, it was concentrated to remove the solvent. The resulting syrup was dissolved in deionized water and washed three times with ethyl acetate. The aqueous phase was concentrated to obtain compound 4 as a white solid (172 mg, 0.68 mmol, yield 96%).

[0046]

[0047] The structural characterization data of the obtained compound 4 is: 1 H NMR (400MHz, Methanol-d 4 )δ4.61–4.53(m,1H),4.30–4.18(m,2H),3.94(d,J=2.5Hz,1H),3.93–3.87(m,1H),3.64–3.54(m,1H) ,3.49(dd,J=8.5,0.8Hz,1H),3.01(dd,J=13.4,3.4Hz,1H),2.93(dd,J=13.4,5.7Hz,1H),2.20–2.09(m,2H ),1.30(t,J=7.1Hz,3H).

[0048] 2. Add 132mg (0.53mmol) of compound 4, 305mg (0.68mmol) of pentafluorophenol octadecylcarboxylate, and 111μL (0....

Embodiment 3

[0057] 1. Dissolve 396mg (1.44mmol) of compound 1 in 6mL of methanol, add 13.34mL of 0.5mol / L lithium hydroxide aqueous solution dropwise to it under stirring at room temperature, stir the resulting mixture for 4 hours at room temperature, and neutralize it with an acidic ion exchange resin To neutrality, it was filtered and concentrated to obtain compound 2 (340 mg, 1.38 mmol, yield 96%), and the obtained crude product was directly used in subsequent reactions.

[0058]

[0059] 2. Dissolve 184mg (0.73mmol) of compound 2, 173mg (0.81mmol) of saturated tetradecylamine in 4mL of DMF, and add 172mg (0.90mmol) of EDCI, 118mg (0.56mmol) of HOBt and 300μL (1.82mmol) DIPEA, stirred at room temperature for 12h, concentrated to remove the solvent, and the obtained syrup was dissolved in CH 2 Cl 2 after dissolving with H 2 Washed with O, the organic phase was collected and washed with Na 2 SO 4 Drying, filtration and concentration, column chromatography (CH 2 Cl 2 / MeOH=10:1, ...

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PUM

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Abstract

The invention discloses a glycolipid derivative based on Kdo as well as preparation and antibacterial application of the glycolipid derivative. The structural formula of the derivative is shown in the description, wherein in the formula, R1 is aliphatic amino (namely CH3(CH2)nNH-, n is equal to 1-17), and R2 is equal to -NH3 + Cl-; or R1 is -OH or -O-NH4+, and R2 is RCONH- (R is C1-18 saturated or unsaturated alkyl). Compared with the reported glycolipid, the glycolipid disclosed by the invention is a non-natural glycolipid compound prepared on the basis of an important monosaccharide Kdo (3-deoxy-D-mann-2-octanone acid) derived from gram-negative bacteria, and the compound can be used as a novel antibacterial substance.

Description

technical field [0001] The invention belongs to the technical field of synthesis of glycolipid compounds, in particular to a kind of rare monosaccharide Kdo (3-deoxy-D-mannose-2-octulose acid) in Gram-negative bacteria, plants, algae and other organisms ) is a glycolipid derivative with a backbone. The compounds can be used as potential novel antibacterial compounds to inhibit the growth of Gram-positive bacteria and Gram-negative bacteria. Background technique [0002] Natural glycolipids have the advantages of low toxicity, degradability, regeneration, and environmental friendliness. Natural glycolipids represented by sophorolipids, trehalolipids, and rhamnolipids can reduce surface and interfacial tension and promote the formation of detergent foam. Formation and wetting ability are widely used in cosmetics, medicine, environmental protection and energy-saving technology. Importantly, glycolipids can also induce the formation of pores or ion channels in cell membranes, ...

Claims

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Application Information

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IPC IPC(8): C07D309/10A61P31/04
CPCY02A50/30
Inventor 冯颖乐柴永海刘爱云张琦
Owner SHAANXI NORMAL UNIV
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