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Application of Cleistanone dimethylamine derivative in preparation of anti-rhinitis drugs

A technology of occlone and derivatives, which is applied in the directions of drug combinations, medical preparations containing active ingredients, pharmaceutical formulations, etc., can solve the problems of poor curative effect and ineffectiveness of rhinitis, and achieve good anti-rhinitis effect.

Active Publication Date: 2014-10-08
南通香境生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, antihistamine drugs such as terfenadine or antiallergic drugs such as tranilast and ketotifen are mainly used in the treatment of rhinitis. These drugs have poor or ineffective effects on chronicity and recurrent rhinitis

Method used

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  • Application of Cleistanone dimethylamine derivative in preparation of anti-rhinitis drugs
  • Application of Cleistanone dimethylamine derivative in preparation of anti-rhinitis drugs
  • Application of Cleistanone dimethylamine derivative in preparation of anti-rhinitis drugs

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.Volume2011, Issue 22, pages 4108-4111, August 2011) method.

[0020]

Embodiment 2

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

[0022] Compound I (440mg, 1.00mmol) was dissolved in 10mL of benzene, tetrabutylammonium bromide (TBAB) (0.04g), 1,2-dibromoethane (3.760g, 20.00mmol) and 6mL of benzene were added to the solution 50% sodium hydroxide solution. The mixture was stirred at 25 degrees Celsius for 24 h. After 24h, the reaction solution was poured into ice water, immediately extracted with dichloromethane twice, and the organic phase solutions were combined. Then the organic phase solution was washed 3 times with water and saturated brine in turn, and then dried over anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain the 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...

Embodiment 3

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

[0028] Compound II (273mg, 0.5mmol) was dissolved in 20mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and dimethylamine (900mg, 20mmol) were added to it, and the mixture was heated to reflux for 16h . After the reaction, the reaction solution was poured into ice water, extracted three times with the same amount of dichloromethane, and the organic phases were combined. The combined organic phase was washed with water and saturated brine in turn, 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 light yellow concentrated elution band was collected to obtain compound III as a light yellow solid (160.7 mg, 61%).

[0029] 1H NMR (500MHz, DMSO-d6)...

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Abstract

The invention relates to the field of organic synthesis and pharmaceutical chemistry and particularly relates to a Cleistanone derivative, a preparation method thereof and use thereof in the preparation of anti-rhinitis drugs. According to the invention, a novel Cleistanone derivative is synthesized, and a preparation method of the novel Cleistanone derivative is disclosed. Shown by pharmacological experiments, the Cleistanone 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 cleistanone derivatives, preparation methods and uses 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, the treatment of rhinitis mainly uses antihistamines such as terfenadine or anti-allergic drugs such as tranilast and ketotifen. These drugs have poor or ineffective effects on the chronicity and recurrent rhinitis. Therefore, small molecule compounds with clear ingredients, controllable quality, safe and efficient, have potential value in the development of rhinitis treatment drugs. [0003] It is most important 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 eff...

Claims

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Application Information

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IPC IPC(8): A61K31/56A61P37/08A61P11/02C07J63/00
Inventor 罗东君江春平吴俊华
Owner 南通香境生物医药科技有限公司
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