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Application of composition of pyrrolidine derivative and morpholinyl derivative of Virosaine A to anti-inflammatory medicine

A composition and drug technology, which can be used in drug combinations, anti-inflammatory agents, medical preparations containing active ingredients, etc., and can solve the problems of low safety and high toxicity.

Inactive Publication Date: 2016-08-17
NANJING FUHAIAOSAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The existing drugs for the treatment of inflammation have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity

Method used

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  • Application of composition of pyrrolidine derivative and morpholinyl derivative of Virosaine A to anti-inflammatory medicine
  • Application of composition of pyrrolidine derivative and morpholinyl derivative of Virosaine A to anti-inflammatory medicine
  • Application of composition of pyrrolidine derivative and morpholinyl derivative of Virosaine A to anti-inflammatory medicine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The preparation of embodiment 1 compound Virosaine A

[0016] The preparation method of compound Virosaine A (I) refers to the literature (Bing-Xin Zhao et al., 2012. Virosaines A and B, Two New Birdcage-Shaped Securinega Alkaloids with an Unprecedented Skeleton from Flueggea virosa. Organic Methods of Letters 14 (2012) 3096–3099).

[0017]

Embodiment 2

[0018] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Virosaine A

[0019] Compound I (235 mg, 1.00 mmol) was dissolved in 20 mL of benzene, tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 5 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 8 h. After 8 hours, 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 with water and saturated brine three times 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=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (261mg, 78%) .

...

Embodiment 3

[0025] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of Virosaine A

[0026] Compound II (171 mg, 0.5 mmol) was dissolved in 15 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and pyrrolidine (1420 mg, 20 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 twice 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=100:1.5, v / v), and the light yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl derivative of Virosaine A Compoun...

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Abstract

The invention discloses an application of a composition of a pyrrolidine derivative and a morpholinyl derivative of Virosaine A to anti-inflammatory medicine, relates to the field of organic synthesis and medicinal chemistry, in particular to the composition, a preparing method and the application of the composition to anti-inflammatory medicine preparing, and discloses the composition and the preparing method thereof. Pharmacological experiments show that the composition has the anti-inflammatory effect, and has the anti-inflammatory medicine developing value.

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] Inflammation occurs locally but can also affect the whole body. Local clinical features are redness, heat, swelling, pain and dysfunction. Redness and heat are due to the expansion of local blood vessels and the acceleration of blood flow due to inflammation. Swelling is caused by local inflammatory hyperemia and exudation of blood flow components. The development of drugs with anti-inflammatory effects is of great significance for the verification of relief and pain relief. [0003] The existing drugs for the treatment of inflammation have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs...

Claims

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Application Information

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IPC IPC(8): A61K31/5377A61K31/439A61P29/00C07D498/22
CPCA61K31/5377A61K31/439C07D498/22A61K2300/00
Inventor 王卓婷
Owner NANJING FUHAIAOSAI PHARMA CO LTD
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