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Holarrhine alkaloid derivative and application of holarrhine alkaloid derivative

A technology of alkaloid derivatives and antidiarrheal wood, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve the problems of large dosage and weak effect

Active Publication Date: 2014-12-24
LANZHOU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Although the above-mentioned total alkaloids of antidiarrheal wood have a certain inhibitory effect on acetylcholinesterase and can be used to prepare anti-senile dementia drugs, they are weaker than the drugs used on the market such as huperzine A, and the dosage is large

Method used

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  • Holarrhine alkaloid derivative and application of holarrhine alkaloid derivative
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  • Holarrhine alkaloid derivative and application of holarrhine alkaloid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: conespinine (compound 1 ) preparation

[0031] Put 2 kg of crushed antidiarrheal wood (powder) into a 20L round-bottomed flask, then reflux extract with 13L 90% ethanol for 3 hours, filter, filter the filter residue with 12L 90% ethanol for reflux extraction for 2 hours, filter, combine the two filtrates and concentrate.

[0032] Dissolve the resulting solid in water, then transfer it to a 5L beaker, adjust the pH to 2 with 4M HCl, filter after standing overnight, adjust the pH to 11 with 4M NaOH, then extract with an equal volume of chloroform, and distill under reduced pressure to obtain 200g of total alkaloids of B.

[0033] The total alkaloids of Zhixie wood were heated and dissolved with redistilled ethanol, and then separated and purified with macroporous resin.

[0034] Gradient elution was performed with 20%, 30%, 40%, 50%, 60%, 70%, and 80% ethanol in water.

[0035] will contain conespinine (compound 1 ) components were combined, and then se...

Embodiment 2

[0038] Example 2: N-3 demethylated derivatives of antidiarrheal wood alkaloids (compound 2 ) preparation

[0039] a step reaction:

[0040] 2 g (6 mmol) of dried antidiarrheal alkaloids (compound 1 ) into a 50mL round bottom flask, dissolved in 20mL of anhydrous methanol, then added dropwise 5mL of 30% hydrogen peroxide, and reacted overnight at room temperature.

[0041] Add 10 mL of distilled water to the reaction solution, stir evenly, extract 3 times with chloroform, extract the solution after drying with sodium sulfate, filter and concentrate, and purify by silica gel column chromatography to obtain the compound 1 3-position N-oxide.

[0042] Step b reaction:

[0043] the above compound 1Add the 3-position N oxide into a 50mL round bottom flask, dissolve it with 20mL of anhydrous methanol, add FeSO 4 ·7H 2 0 3.3g (12mmol), react overnight under nitrogen protection at room temperature.

[0044] Then add 10 mL of saturated NaHCO to the reaction soluti...

Embodiment 3

[0048] Example 3: Preparation of 2-bromoethylphenol ethers 6a-6k.

[0049] Add 0.01mol of phenol, 0.5g (0.012mol) of NaOH, 0.05g of TBAB, and 0.05g of KI into a three-necked flask, and add 20mL of distilled water.

[0050] Heat to completely dissolve the ingredients.

[0051] When the temperature reaches 90°C, start to drop 1.3mL (0.015mol) of 1,2-dibromoethane, control the reaction at about 100°C, and react for 5h.

[0052] After the reaction was completed, it was cooled, and the water layer was removed. The organic layer was washed twice with 2% NaOH aqueous solution, once with saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated.

[0053] Silica gel column chromatography purification.

[0054] 2-bromoethylphenol ether 6a-6k (yield 80% - 90%) was obtained.

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Abstract

The invention discloses a holarrhine alkaloid derivative and an application of holarrhine alkaloid derivative. The structure of the holarrhine alkaloid derivative disclosed by the invention is as general formula (I), wherein R represents substituted phenyl or substituted naphthyl and specifically represents the following groups: phenyl, paranitrophenyl, p-methyl phenyl, p-methoxy phenyl, 2,4-dichlorophenyl, p-chlorophenyl, 2,4-dinitrophenyl, 2-naphthyl, 1-naphthyl, 4-chlorine-1-naphthyl and methoxy phenyl. The invention further discloses an application of the holarrhine alkaloid derivative in preparation of a medicine for preventing and treating alzheimer's disease or a medicine for improving the intelligence.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and pharmacotherapeutics, and specifically relates to the synthesis of N-3 substituted antidiarrheal alkaloid derivatives and their application in the preparation of drugs for preventing and treating senile dementia or improving intelligence. Background technique [0002] Alzheimer's disease (Alzheimer2.isease, senile dementia, referred to as AD) is a chronic progressive brain degenerative disease, clinically with cognitive decline as the core symptom. [0003] The incidence of AD is positively correlated with age, and it is the main type of senile dementia. [0004] In recent years, clinical studies at home and abroad have shown that acetylcholinesterase inhibitors are the most effective drugs for the treatment of AD, and also have a good effect on the treatment of glaucoma, myasthenia gravis, and intestinal obstruction (Jin Youyu. Pharmacology (No. Fifth Edition), 2001; 54-55.). [0005] Cur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61P25/28
Inventor 杨中铎靳国斐盛捷舒宗美张新国
Owner LANZHOU UNIVERSITY OF TECHNOLOGY
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