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

A technology of ethyl derivatives, cleistanone, applied in the field of preparation, O-ethyl derivatives of cleistanone, to achieve good anti-rhinitis effect

Active Publication Date: 2015-03-11
NANJING UNIV
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  • Summary
  • 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-(imidazolyl) ethyl derivative, and preparation method and application thereof
  • Cleistanone O-(imidazolyl) ethyl derivative, and preparation method and application thereof
  • Cleistanone O-(imidazolyl) ethyl derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Preparation of the compound Cleistanone

[0019] The preparation method of compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011. Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton. Volume 2011, Issue 22 , pages 4108–4111, August 2011).

[0020]

Embodiment 2

[0021] Example 2 Synthesis of O-bromoethyl derivative (II) of Cleistanone

[0022] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and to the solution was added 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 24h. After 24 h, the reaction solution was poured into ice water, immediately extracted twice with dichloromethane, and the organic phase solutions were combined. Then, the organic phase solution was washed with water and saturated brine three times in turn, dried over 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 bands were collected to obtain compound II as a yellow solid (344 mg, 63%).

[0023] 1H NMR (500MH...

Embodiment 3

[0027] Example 3 Synthesis of O-(imidazolyl)ethyl derivative (III) of Cleistanone

[0028] Compound II (273 mg, 0.5 mmol) was dissolved in 35 mL of acetonitrile, anhydrous potassium carbonate (690 mg, 5.0 mmol), potassium iodide (252 mg, 1.5 mmol) and imidazole (870 mg, 10 mmol) were added thereto, and the mixture was heated to reflux for 3 h. After the reaction, the reaction solution was poured into 45 mL of ice water, extracted three times with the same amount of dichloromethane, and the organic phases were combined. The combined organic phases were washed successively 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=100:0.2, v / v), and the brown concentrated elution bands were collected to obtain a brown solid of the O-(imidazolyl)ethyl derivative of Cleistanone ...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, in particular to a Cleistanone O-(imidazolyl) ethyl derivative, and a preparation method and application thereof in the preparation of anti-rhinitis drugs. The invention synthesizes a new Cleistanone O-(imidazolyl) ethyl derivative and discloses a preparation method thereof. Pharmacological experiments prove that the Cleistanone O-(imidazolyl) ethyl derivative has the effect of resisting to rhinitis and has the value of anti-rhinitis drug development.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to an O-(imidazolyl) ethyl derivative of Cleistanone, a preparation method and use thereof. Background technique [0002] Rhinitis is a common clinical disease and frequently-occurring disease. The occurrence of rhinitis is mainly related to allergic reactions and belongs to the category of immune inflammation. At present, antihistamines such as terfenadine or antiallergic drugs such as tranilast and ketotifen are mainly used for the treatment of rhinitis. Therefore, small molecule compounds with clear composition, controllable quality, safety and high efficiency have potential value in the development of rhinitis treatment drugs. [0003] It is of great value to find compounds or lead compounds from natural products and modify their structures to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity. [0004] At p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/58A61P11/02
CPCC07J63/008
Inventor 王慧吴俊艺吴俊华
Owner NANJING UNIV
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