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Application of Harrisotone A imidazolyl and benzimidazolyl derivative composition in acute-gout-resistant medicine

A technology of acute gout and composition, which is applied in the field of organic synthesis and medicinal chemistry, and can solve problems such as aplastic anemia and neutropenia

Inactive Publication Date: 2017-05-24
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although they have fast anti-inflammatory and analgesic effects, their toxic and side effects are also quite obvious. For example, the effective dose of colchicine is similar to the dose that produces diarrhea and other gastrointestinal symptoms. Absolutely contraindicated in the case of bleeding, and the administration of phenylbutazone for as short as 3 weeks can also cause severe neutropenia or aplastic anemia

Method used

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  • Application of Harrisotone A imidazolyl and benzimidazolyl derivative composition in acute-gout-resistant medicine
  • Application of Harrisotone A imidazolyl and benzimidazolyl derivative composition in acute-gout-resistant medicine
  • Application of Harrisotone A imidazolyl and benzimidazolyl derivative composition in acute-gout-resistant medicine

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Embodiment 1

[0016] The preparation of embodiment 1 compound Harrisotone A

[0017] The preparation method of compound Harrisotone A (I) refers to the literature published by Sheng Yin et al. (Sheng Yin et al., 2009.Harrisotones A–E, five novel prenylated polyketides with a rarespirocyclic skeleton from Harrisonia perforata.Tetrahedron 65(2009) 1147–1152 )Methods.

[0018]

Embodiment 2

[0019] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Harrisotone A

[0020] Compound I (472 mg, 1.00 mmol) was dissolved in 15 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 3 h. After 3h, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed twice with water and saturated brine successively, then dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1.5, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a yellow powder of compound II (602mg, 76%) .

[00...

Embodiment 3

[0024] Synthesis of O-(imidazolyl) ethyl derivative (III) of embodiment 3 Harrisotone A

[0025] Compound II (396 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and imidazole (3480 mg, 40 mmol) were added thereto, and the mixture was heated to reflux for 1 h. After the reaction, the reaction solution was poured into ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:0.6, v / v), and the light brown concentrated elution band was collected and concentrated to obtain a light brown solid of compound III (271.4mg, 72% ...

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Abstract

The invention discloses application of Harrisotone A imidazolyl and benzimidazolyl derivative composition in acute-gout-resistant medicine, namely application of composition of O-(imidazolyl) ethyl derivative and O-(benzimidazolyl) ethyl derivative of Harrisotone A in the acute-gout-resistant medicine. The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to Harrisotone A derivative composition and a preparation method and application of the Harrisotone A derivative composition in preparation of acute-gout-resistant medicine. The invention discloses the Harrisotone A derivative composition and the preparation method thereof. Pharmacological experiments show that the Harrisotone A derivative composition disclosed by the invention has an acute-gout-resistant effect and has value of developing acute-gout-resistant medicine.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a composition, a preparation method and an application thereof. Background technique [0002] Gout, also known as gouty arthritis, is a disease caused by the disorder of purine metabolism in the body. It is manifested by excessive uric acid in the blood, and it is easy to cause urate (MSU) to crystallize in joints and other tissues. The acute attack of gout is due to the local neutrophil infiltration and inflammatory response caused by MSU deposited in the joints. [0003] Western medicine selects three kinds of medicines for use in the acute attack stage of gout: colchicine, non-steroidal anti-inflammatory drugs and corticosteroids. The mechanism of action of colchicine is to bind to the tubulin of neutrophils, thereby hindering the activity of granulocytes and inhibiting granulocyte infiltration. Non-steroidal anti-inflammatory drugs such as indometha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4184A61P19/06C07D233/60C07D235/06A61K31/4178
CPCA61K31/4178A61K31/4184C07D233/60C07D235/06A61K2300/00
Inventor 华子春吴俊华刘超慧
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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