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Mesaconitine acylated product nitrous oxide, preparation and use

A technology of aconitine acylate and nitrogen oxides, which is applied in the synthesis of pesticides and pharmaceuticals, and can solve the problems of poor nitrogen oxidation reaction, research on the activity of non-derivatives, and non-nitrogen oxidation reactions.

Inactive Publication Date: 2009-05-20
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the structural modification of nitrogen atom oxidation using mesoaconitine and its acylate as raw materials.
However, there are literature reports abroad about the nitrogen oxidation reaction of norditerpene alkaloids. Bai Yili et al. carried out nitrogen oxidation reactions on norditerpene alkaloids such as aconitine and hypoconitine, and synthesized 8 norditerpene alkaloids. Structural confirmation was carried out, and it was found that the nitrogen oxidation reaction is not effective when there is a hydroxyl group at the 3-position
However, it did not perform nitrogen oxidation reaction on aconitine acylate, nor did it conduct activity research on derivatives

Method used

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  • Mesaconitine acylated product nitrous oxide, preparation and use
  • Mesaconitine acylated product nitrous oxide, preparation and use
  • Mesaconitine acylated product nitrous oxide, preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Dissolve 209 mg of aconitine in 2 mL of pyridine, then add 1.5 mL of acetic anhydride dropwise, and stir at room temperature for 20 hours. The pH was adjusted to 9 with saturated sodium carbonate solution, and after extraction with chloroform, the chloroform layer was washed with water three times and dried, and distilled under reduced pressure to obtain 240.9 mg of the acetylated product of aconitine. Slowly add 246.3 mg of dissolved m-chloroperoxybenzoic acid to the chloroform solution of aconitine acetylation product under stirring at room temperature, and adjust the pH to 9 after reacting for 10 hours. After chloroform extraction, the chloroform layer is washed 3 times with water and dried. Distillation under reduced pressure gave 245.3 mg of the mixture. The mixture was separated on a silica gel column and eluted sequentially with 200 mL chloroform / methanol=150:1 and 300 mL chloroform / methanol=50:1 to obtain 56 mg of nitroxide-3-O-acetyl mesaconitine.

[0014] The...

Embodiment 2

[0018] Dissolve 200 mg of aconitine in 2 mL of pyridine, then add 1.5 mL of propionic anhydride dropwise, and stir at room temperature for 20 hours. Adjust the pH to 9 with saturated sodium carbonate solution, extract with chloroform, wash with water three times, dry, and distill under reduced pressure to obtain 219 mg of aconitine propionylation product. Then, 226.9 mg of dissolved m-chloroperoxybenzoic acid was slowly added to the solution of aconitine propionylation product under stirring at room temperature. After reacting for 10 hours, the pH was adjusted to 9. After extraction with chloroform, the chloroform layer was washed with water for 3 times and dried. , Distilled under reduced pressure to obtain 146.6 mg of the mixture. The mixture was separated on a silica gel column and eluted sequentially with 200ml chloroform / methanol=100:1 and 200mL chloroform / methanol=50:1 to obtain 71mg of nitroxide-3-O-propionyl mesaconitine.

[0019] The product structure was confirmed b...

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Abstract

The invention discloses a preparation method of a nitrogen oxide (with a compound structure shown as the picture) of an aconitine acylate product and an application thereof, pertaining to the technical field of medical and pesticide synthesis. The preparation method of the nitrogen oxide of the aconitine acylate product comprises the steps that the aconitine acylate product which is served as a raw material and a metachloroperbenzoic acid (mCPBA) which is served as an oxidant are stirred for reaction for 3 hours to 20 hours at temperature of 10 DEG C to 40 DEG C; extraction is carried out after pH value is adjusted to between 8 to 10; then the nitrogen oxide of the aconitine acylate product is obtained by means of column chromatography and separation after pressure reduction and distillation. The compound has obvious desinsection activity and remarkable activities of easing pain, resisting against arrhythmia and tumors, and the like, and can be used for developing new products in respect of medicines, pesticides, etc. In the formula, R refers to alkyl with 1 to 4 carbon atoms while R1, R2 and R3 refer to hydrogen atoms, hydroxyl, aliphatic acyl or aromaticacyl radical.

Description

(1) Technical field [0001] The invention relates to a synthesis method and an application thereof, which belong to the technical field of medicine and pesticide synthesis. (2) Technical background [0002] Aconitine is the main component of aconitine, a natural medicinal material produced in Sichuan. Aconitum is the root of Aconitum carmichaeli Debx., a plant of Ranunculaceae. It is a well-known and commonly used traditional Chinese medicine in my country. Pain relief, heart strengthening, recovery of yang and rescue of adversity, etc. Li Wenlan et al. summarized the pharmacological studies of aconitum alkaloids, showing that they mainly have anti-inflammatory, analgesic, cardiotonic, anti-cancer and anti-arrhythmic effects. However, it is classified as an inferior drug because of its great toxicity, and many poisoning incidents occur clinically, which hinders its medicinal value. Therefore, there are more and more studies on the structure-activity relationship of diterpene...

Claims

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Application Information

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IPC IPC(8): C07D221/22A01N43/42A01P7/00A61K31/439A61P29/00A61P9/06A61P35/00
Inventor 杨海君侯大斌王惠袁小红马林王朝阳叶平
Owner SOUTHWEAT UNIV OF SCI & TECH
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