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Nitric oxide donor type hexadecadrol as well as preparation method and purpose thereof

A technology of dexamethasone and nitric oxide, applied in the field of biomedicine, can solve the problem of no obvious advantages in anti-inflammatory activity, and achieve the effects of reducing bacterial colonization and inflammatory pathological damage, inhibiting biofilm formation, and reducing side effects.

Active Publication Date: 2015-10-28
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although a small number of people are currently studying NO-dexamethasone, the resulting NO-dexamethasone has no obvious advantages in anti-inflammatory activity compared with dexamethasone

Method used

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  • Nitric oxide donor type hexadecadrol as well as preparation method and purpose thereof
  • Nitric oxide donor type hexadecadrol as well as preparation method and purpose thereof
  • Nitric oxide donor type hexadecadrol as well as preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of embodiment 1 methyl 4-hydroxycyclohexanecarboxylate (2)

[0046] Dissolve 3.12g of methyl 4-oxocyclohexylcarboxylate (1) (20mmol) in 50mL of methanol, and add 1.90g of sodium borohydride (50mmol) in portions under stirring. After TLC shows that the reaction is complete, the solvent is removed under reduced pressure, and the remaining The mixture was added with ice water (50 mL), stirred for 30 minutes and then extracted with dichloromethane (20 mL×4). Dry over anhydrous sodium sulfate, filter, remove the solvent, and distill the residue under reduced pressure in an oil pump to obtain 2.88 g of a colorless liquid product, yield: 91.1%.

Embodiment 2

[0047] The synthesis of embodiment 2 4-bromocyclohexanecarboxylic acid (3)

[0048] A mixture of methyl 4-bromocyclohexylcarboxylate (2.88 g, 1.82278 mmol) and concentrated hydrobromic acid (25 mL) was heated to 50° C. and stirred for 24 hours. After the reaction solution was cooled, it was extracted four times with dichloromethane (10 mL×4), and the extracts were combined and dried over anhydrous sodium sulfate. Filtrate, spin to dry the solvent, dissolve the residue in ethyl acetate (10 mL), slowly add petroleum ether (about 100 mL) dropwise under stirring, stir for 5 h under cooling in an ice-water mixed bath, collect the solid by filtration to obtain 1.92 g of white crystalline powder, Yield: 50.9%.

Embodiment 3

[0049] Example 3 Synthesis of 4-bromocyclohexyl chloride (4)

[0050] Add 1.92g of compound 3 (9.275mmol) and 10mL of thionyl chloride into a 250mL dry three-necked flask, install a condenser tube with anhydrous calcium chloride drying tube, heat the oil bath to 70°C, and reflux for 4 hours. Atmospheric distillation removed excess thionyl chloride, and the residue was distilled under reduced pressure to collect high-boiling fractions (oil pump decompression). 1.54 g of a colorless liquid product was obtained, yield: 73.65%.

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Abstract

The invention relates to nitric oxide donor type hexadecadrol as well as a preparation method and application thereof. The nitric oxide donor type hexadecadrol as a compound is obtained by enabling nitrous acid ester to be connected with hexadecadrol through ethyl cyclohexanecarboxylate; the in-vitro antiinflammatory activity of the nitric oxide donor type hexadecadrol is better than that of the hexadecadrol; besides, the nitric oxide donor type hexadecadrol can restrain the growth of methicillin-resistant staphylococcus aureus (MRSA) in vitro, restrain the formation of MRSA biomembrane, and lead to the death of bacteria in the MRSA biomembrane. In addition, the compound can notably increase the survival rate of mice in MRSA sepsis lethal models, reduces the inflammation pathology damage of the mice in sub-sepsis models, decreases the constant value number of bacteria, and has notable advantages in the respect of preventing and treating MRSA sepsis.

Description

technical field [0001] The present invention relates to the field of biomedicine, further, the present invention relates to a nitric oxide donor type dexamethasone and its preparation method and use Background technique [0002] Inflammation refers to the pathological process of living tissue with vascular system, which is mainly defensive response to the damage caused by various inflammatory factors, and its pathological changes are degeneration, exudation and hyperplasia. Many diseases, including various inflammatory diseases (pneumonia, nephritis, rheumatoid arthritis, etc.), coronary heart disease, Alzheimer's disease, and even diabetes, are closely related to inflammatory responses. In the process of inflammatory response, inflammatory factors cause a series of reactions in the body, mainly including changes in the vascular system, which are beneficial to eliminate inflammatory factors, dilute toxins, phagocytize self-injured cells, etc., and promote the repair of tissu...

Claims

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Application Information

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IPC IPC(8): C07J41/00A61K31/573A61P29/00A61P31/04
CPCC07J41/005
Inventor 李海波孙红武邹全明曾浩高钰琪杨赟郭玲
Owner ARMY MEDICAL UNIV
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