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An active oxygen-responsive antioxidant nitric oxide donor, its preparation and application

A nitric oxide and antioxidant technology, applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, antidote, etc. Overcome the problem of single function, long half-life and good stability

Active Publication Date: 2022-03-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In addition, most of the nitric oxide donors reported now have a single function, but diseases are often the result of a combination of factors, especially many diseases are accompanied by inflammation, and the reactive oxygen species produced by inflammatory cells will Causes damage to normal cells, leading to exacerbation of the condition

Method used

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  • An active oxygen-responsive antioxidant nitric oxide donor, its preparation and application
  • An active oxygen-responsive antioxidant nitric oxide donor, its preparation and application
  • An active oxygen-responsive antioxidant nitric oxide donor, its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]Dissolve 15g of 4-hydroxymethylphenylboronic acid pinacol ester (PBAP) in 100mL of chloroform, add 6g of 2-nitrocarbonylimidazole (CDI), stir at 25°C for 2 hours, extract the product with water, and wash with anhydrous sodium sulfate After drying and filtering, the filtrate was rotary evaporated under reduced pressure to obtain 4-nitrocarbonylimidazolylphenylboronic acid pinacol ester (PBAP-CDI), with a yield of >95% and a purity of >98%.

[0044] Dissolve 5g of PBAP-CDI in 25mL of dichloromethane, add 8.5g of 5-monoisosorbide nitro (ISN) and 3.2g of 4-dimethylaminopyridine (DMAP), and stir at 20°C for 72 hours, the product After extracting with water and drying with phosphorus pentoxide, the filtrate was rotary evaporated under reduced pressure, and dried in a vacuum oven to obtain 4-nitrocarbonyl-(5-mononitroisosorbide)-phenylboronic acid pinacol ester ( PBAP-ISN), yield>85%, purity>98%.

[0045] The proton nuclear magnetic resonance spectra of the obtained PBAP-CDI a...

Embodiment 2

[0047] Dissolve 500g of 4-hydroxymethylphenylboronic acid pinacol ester (PBAP) in 1000mL of toluene, add 250g of 2-nitrocarbonylimidazole (CDI), stir at 0°C for 48 hours, extract the product with water, and use anhydrous magnesium sulfate After drying and filtering, the filtrate was rotary evaporated under reduced pressure to obtain 4-nitrocarbonylimidazolylphenylboronic acid pinacol ester (PBAP-CDI), with a yield of >95% and a purity of >98%.

[0048] Dissolve 200g of PBAP-CDI in 200mL of dioxane, add 300g of 5-monoisosorbide nitrate (ISN) and 72g of pyridine, stir at 75°C for 2 hours, extract the product with water, and carry out anhydrous magnesium sulfate After drying, the filtrate was rotary evaporated under reduced pressure, and dried in a vacuum oven to obtain 4-nitrocarbonyl-(5-mononitroisosorbide)-phenylboronic acid pinacol ester (PBAP-ISN) yield 90%.

Embodiment 3

[0050] Dissolve 5g of 4-hydroxymethylphenylboronic acid pinacol ester (PBAP) in 50mL of dimethyl sulfoxide, add 10g of 2-nitrocarbonylimidazole (CDI), stir at 60°C for 24 hours, extract the product with water, and use Phosphorus pentoxide was dried and filtered, and the filtrate was rotary evaporated under reduced pressure to obtain 4-nitrocarbonylimidazolylphenylboronic acid pinacol ester (PBAP-CDI). Yield98%

[0051] Dissolve 2g of PBAP-CDI in 10mL of anisole, add 3g of 5-monoisosorbide (ISN) and 5.7g of 4-dimethylaminopyridine (DMAP), stir at 90°C for 24 hours, and extract the product with water , and after drying with anhydrous sodium sulfate, the filtrate was rotary evaporated under reduced pressure, and dried in a vacuum oven to obtain 4-nitrocarbonyl-(5-mononitroisosorbide)-phenylboronic acid pinacol ester (PBAP- ISN), yield>95%, purity>98%.

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Abstract

The present invention relates to the field of medicinal chemistry, in particular to an active oxygen-responsive antioxidant nitric oxide donor, its preparation and application. The donor has the following structural formula, and its preparation method is to react PBAP and CDI to obtain PBAP-CDI; React with ISN under the action of catalyst to obtain antioxidant nitric oxide donor. The active oxygen-responsive antioxidant nitric oxide donor of the present invention has good stability, long half-life in physiological environment, and can only be decomposed under the stimulation of high concentration active oxygen in inflammatory tissue, releasing antioxidant and nitric oxide donor , without side effects on normal tissues. At the same time, it can effectively scavenge active oxygen and play an anti-oxidation role; it can promote the growth of endothelial cells and at the same time inhibit the growth of smooth muscle cells, which is conducive to the rapid endothelialization of the cardiovascular system. It has diversified functions and can be widely used in drug development. Promote application value.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an active oxygen-responsive antioxidant nitric oxide donor, its preparation and application. Background technique [0002] Nitric oxide (NO) is an important gas signal molecule in living organisms. It can participate in the regulation of various physiological functions in living organisms and play extremely important functions in vivo. For example, nitric oxide is involved in processes such as vascular regulation, neurotransmission, inflammation and immune response. Nitric oxide can also induce apoptosis of macrophages, cardiomyocytes, vascular smooth muscle cells, and pancreatic islet cells. In addition, a large number of studies have shown that nitric oxide is closely related to tumors. Low concentrations of nitric oxide can promote tumor growth, while high concentrations of nitric oxide can inhibit tumor growth. [0003] In view of the low concentration of endogenous nitri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61K31/69A61P9/00A61P29/00A61P39/06
CPCC07F5/025A61P29/00A61P39/06A61P9/00
Inventor 计剑金桥贾凡
Owner ZHEJIANG UNIV