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Cleistanone O-(morpholinyl)ethyl derivative and preparation method and application thereof

A kind of technology of ethyl derivative and cleistanone, which is applied to the O-ethyl derivative of cleistanone, the preparation field, and achieves the effect of good anti-rhinitis

Active Publication Date: 2014-12-10
NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For the treatment of rhinitis at present, there is no clinically effective drug, and most drugs have unavoidable toxic and side effects while relieving the symptoms of rhinitis. Search for compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain high-efficiency and low-efficiency drugs. Potential drugs for poisons are of great value

Method used

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  • Cleistanone O-(morpholinyl)ethyl derivative and preparation method and application thereof
  • Cleistanone O-(morpholinyl)ethyl derivative and preparation method and application thereof
  • Cleistanone O-(morpholinyl)ethyl derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1 Preparation of Compound Cleistanone

[0019] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. , pages 4108–4111, August 2011).

[0020]

Embodiment 2

[0021] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0022] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 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, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0023] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0027] Example 3 Synthesis of O-(morpholinyl) ethyl derivatives (III) of cleistanone Cleistanone

[0028] Compound II (273 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 morpholine (1742 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 8 h. After the reaction was completed, the reaction solution was poured into 30 mL of 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=100:0.5, v / v), and the yellow concentrated elution band was collected to obtain the yellow color of the O-(morpholino)e...

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Abstract

The invention relates to the field of organic synthesis and pharmaceutical chemistry and particularly relates to a Cleistanone O-(morpholinyl)ethyl derivative, a preparation method thereof and application thereof in the preparation of anti-rhinitis drugs. According to the invention, a novel Cleistanone O-(morpholinyl)ethyl derivative is synthesized, and a preparation method of the novel Cleistanone O-(morpholinyl)ethyl derivative is disclosed. Shown by pharmacological experiments, the Cleistanone O-(morpholinyl)ethyl derivative disclosed by the invention has an anti-rhinitis effect and has a value in the development of the anti-rhinitis drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to an O-(morpholinyl) ethyl derivative of cleistanone, a preparation method and an application thereof. Background technique [0002] Rhinitis is a common and frequently-occurring disease in clinical practice. The occurrence of rhinitis is mainly related to allergic reactions and belongs to the category of immune inflammation. At present, antihistamine drugs such as terfenadine or antiallergic drugs such as tranilast and ketotifen are mainly used for the treatment of rhinitis, and these drugs have poor or ineffective effects on chronicity and recurrent rhinitis. Therefore, small molecular compounds with clear components, quality control, safety and high efficiency have potential value in the development of drugs for rhinitis treatment. [0003] It is of great value to find compounds or lead compounds from natural products and carry out structural modificati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P11/02
Inventor 王慧吴俊艺吴俊华
Owner NANJING UNIV
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