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Derivates of rupestonic acid and uses thereof

A technology of artemisinic acid and derivatives, which is applied in the field of artemisinic acid derivatives, and can solve the problems of high toxicity and side effects and high drug activity

Inactive Publication Date: 2010-05-26
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the high activity of purely chemically synthesized drugs, the toxicity and side effects are also large

Method used

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  • Derivates of rupestonic acid and uses thereof
  • Derivates of rupestonic acid and uses thereof
  • Derivates of rupestonic acid and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Preparation of Artemisinic Acid

[0075] Artemisinic acid is extracted by a conventional continuous extraction method. Take 5 kg of crushed Artemisia annua, extract it three times with 1 liter of 95% ethanol, combine the extracts, extract concentrated extracts, and extract the extracts with ethyl acetate for multiple times . The ethyl acetate layers were combined, concentrated and separated on a silica gel column to obtain a crude product of artemisinic acid, which was recrystallized to obtain a pure product of artemisinic acid as colorless rod-shaped crystals, mp.132-134°C.

[0076] IR(KBr)υ: 3230, 2970-2860, 1720, 1680, 1635, 1415, 1390, 1238, 958cm -1 ; 1 HNMR (600MHz, CDCl 3 ): 0.67 (d, J=7.2Hz, 3H, CH 3 ), 1.63(m, 1H), 1.64(m, 1H), 1.81(m, 1H), 1.84(m, 1H), 1.88(m, 1H), 2.06(m, 1H), 2.14(m, 1H) , 2.46(m, 1H), 2.64(m, 1H), 2.86(m, 1H), 2.90(m, 1H), 3.22(m, 1H), 5.76(s, 1H), 6.40(s, 1H); 13 CNMR (150MHz, CDCl 3 ): 7.9, 12.0, 31.4, 35.1, 36.4, 37.5, 38.2, 41.1,...

Embodiment 2

[0087] According to Example 1, a branch of artemisinic acid was prepared;

[0088] Preparation of Class B Synthesis of Artemisinic Acid Derivatives (Taking the Synthesis of Artemisinic Acid (P-Methyl-Phenyl)-Ester as an Example)

[0089] Add 0.124g (0.5mmol) of artemisinic acid and 0.113g (0.55mmol) of DCC into a 25mL round-bottomed flask, add 8mL of dry THF, stir under ice cooling, and add 0.031g (0.25mmol) of DMAP to the reaction system. After reacting in ice bath for 30 minutes, add 0.128g (0.60mmol) of p-cresol to the reaction system, stir and react in ice bath for 30 minutes, then naturally rise to room temperature and react for 8 hours, filter out the precipitated DCU, concentrate the filtrate and separate by column to obtain the target Compound B-10. The remaining B-type compounds were synthesized according to the synthesis method of B-10. The synthesized compounds were passed through IR, 1 HNMR, ESI-MS and other analytical methods were characterized. Some of these ...

Embodiment 3

[0103] According to Example 1, a branch of artemisinic acid was prepared;

[0104] Preparation of an artemisinic acid amide derivative (A compound) inorganic acid salt or organic acid salt:

[0105] (1) Preparation of N(2-bromo-phenyl)-artemisinic acid amide (A-5) hydrochloride

[0106] Add 0.5mmol of N(2-bromo-phenyl)-artemisinic acid amide into 20mL of 5% hydrochloric acid aqueous solution, stir slightly to dissolve it, add an appropriate amount of ethanol, refrigerate to crystallize, filter, and dry in vacuo to obtain N (2-Bromo-phenyl)-artemisinic acid amide hydrochloride, yield: 66%.

[0107] (2) Preparation of N(2-bromo-phenyl)-artemisinic acid amide (A-5) acetate

[0108] Add 0.5mmol A-5 into a 50mL single-necked round-bottomed flask containing 10mL of dichloromethane, add 2mL of glacial acetic acid, stir at 30-40°C for 1-2h, refrigerate and crystallize after cooling, filter, and dry in vacuo to obtain A-5 vinegar Salt, the yield is about 58%.

[0109] Salts of Clas...

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Abstract

The invention relates to derivates of rupestonic acid and uses thereof. The derivates of rupestonic acid is rupestonic acid derivative A-type or B-type compounds which are prepared through a normal condensation reaction by taking a monomer compound of sesquiterpene isolated from the plant Xinjiang Artemisia rupestric L as a mother compound, and taking a monomer compound of rupestonic acid and an aromatic amine or fatty amine or an organic alcohol as the fatty alcohol or an aromatic alcohol; and then performing structural modification on the rupestonic acid monomer compound to search a natural anti-virus lead compound with high activity taking natural products as a mother compound. An activity test result of the compound proves that: the compound has medicament uses of anti-I, II flu virus and anti-I, II herpes simplex virus infection and is used alone or combined with one or more pharmaceutical acceptable, inert and nontoxic excipients or carriers into a medicinal composition and is the candidate compound for developing antiviral medicaments.

Description

technical field [0001] The present invention relates to a derivative of artemisinic acid and its application, specifically, the structure of the derivative having anti-influenza virus and herpes virus performance and the pharmaceutical composition containing them. Background technique [0002] For a long time, humans have been fighting against viral infections. According to incomplete statistics, about 60% of the world's epidemic infectious diseases are caused by viral infections. At present, there is no specific antiviral drug in clinical practice. The abuse of antibiotics and antiviral drugs has led to increased drug resistance and variability of viruses, resulting in the continuous emergence of new viruses. Therefore, it is necessary to develop antiviral drugs with new structures and new mechanisms of action to meet the needs of society. [0003] Because the drug activity of pure chemical synthesis is high, the toxic side effect is also big. The elimination rate in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/80C07C231/02C07C69/738C07C67/08A61K31/13A61K31/215A61P31/12A61P11/00
CPCC07C69/738C07C2102/30A61K31/215C07C235/78A61K31/16C07C2602/30A61P11/00A61P31/12A61P31/22
Inventor 阿吉艾克拜尔·艾萨雍建平赵江瑜
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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