Application of O-(diethylamino) ethyl derivative of Daphmalenine A in preparation of anti-inflammatory drug

A technology of ethyl derivatives and diethylamine groups, applied in the field of preparation, O-ethyl derivatives, can solve problems such as high toxicity and low safety

Inactive Publication Date: 2015-09-02
NANJING UNIV
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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 O-(diethylamino) ethyl derivative of Daphmalenine A in preparation of anti-inflammatory drug
  • Application of O-(diethylamino) ethyl derivative of Daphmalenine A in preparation of anti-inflammatory drug
  • Application of O-(diethylamino) ethyl derivative of Daphmalenine A in preparation of anti-inflammatory drug

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of embodiment 1 compound Daphmalenine A

[0023] The preparation method of compound Daphmalenine A (I) refers to the literature published by Yu Zhang et al. ,4103–4107) approach.

[0024]

Embodiment 2

[0025] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Daphmalenine A

[0026] Compound I (419 mg, 1.00 mmol) was dissolved in 10 mL of benzene, tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (7.520 g, 40.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 12 h. After 12 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 four 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=100:1.5, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (320 mg, 61%).

[0027] 1H NMR (500MHz,...

Embodiment 3

[0032] The synthesis of the O-(diethylamino) ethyl derivative (III) of embodiment 3 Daphmalenine A

[0033] Compound II (263 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 diethylamine (1460 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 10 h . After the reaction, the reaction solution was poured into ice water, extracted four 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=100:1, v / v), and the yellow concentrated elution band was collected to obtain the O-(diethylamino)ethyl derivative of Daphmalenine A (I...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, in particular to a Daphmalenine A derivative, a preparation method and application of the Daphmalenine A derivative in preparation of anti-inflammatory drug. A new Daphmalenine A derivative is synthesized. Pharmacological experiments show that the Daphmalenine A derivative has anti-inflammatory effect and has value in developing the anti-inflammatory drug.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(diethylamino)ethyl derivatives of Daphmalenine A, a preparation method and uses 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/439A61P29/00C07D491/107
Inventor 吴俊华黄蓉吴俊艺
Owner NANJING UNIV
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