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Substituted methylene pyrones derivatives and their preparing process and use

A methylene and substituent technology, which is applied in the field of 6-aryl-3-methyl-4-acyloxytetrahydropyranone derivatives and their preparation, can solve the problem of limiting the universal applicability of drugs, inability to Satisfaction, malignant killing of normal cells, etc.

Inactive Publication Date: 2006-01-18
浙江海正集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the specific drugs for the treatment of tumor diseases are not satisfactory, and the malignant killing of normal cells caused by the low selectivity of cytotoxic drugs currently used in anti-tumor clinics limits the general applicability of such drugs

Method used

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  • Substituted methylene pyrones derivatives and their preparing process and use
  • Substituted methylene pyrones derivatives and their preparing process and use
  • Substituted methylene pyrones derivatives and their preparing process and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0108] Preparation Example 1: Preparation of Compound I-0 (ethyl 2-methylacetoacetate):

[0109]

[0110] In 300 ml of ethanol, add 13.8 g of sodium metal (600 mmol), after completely dissolving, add 80 ml (600 mmol) of ethyl acetoacetate dropwise, reflux for 1 hour, add dropwise 50 ml (660 mmol) of methyl iodide, reflux for two hours, and cool to room temperature , remove ethanol by rotary evaporation, add water and extract with ether, combine the organic phases, dry over anhydrous sodium sulfate, filter with suction, remove ether by rotary evaporation, distill under reduced pressure, collect 78-80°C (13mmHg) fractions to obtain a colorless transparent liquid 87.63 gram, isolated yield Y=50.71%.

preparation example 2

[0111] Preparation Example 2: Preparation of Compound I-1 (2-methyl-3-oxo-5-hydroxyl-5-(3',4',5'-trimethoxyphenyl)-valeric acid ethyl ester

[0112]

[0113] Under ice-salt bath cooling conditions, 5.78 g (37.5 mmol) of ethyl 2-methylacetoacetate was added dropwise to 2.3 g of sodium hydride (95.8 mmol) in tetrahydrofuran suspension (140 ml), and then 2.5 M 28ml (70.2mmol) of n-hexane solution of butyllithium, after ten minutes, dropwise add 5.88 grams (30mmol) of tetrahydrofuran solution (10ml) of 3,4,5-trimethoxybenzaldehyde, continue to react for 15 minutes, add to the reaction system Add saturated aqueous ammonium chloride solution (30ml), extract with ether, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter with suction, and perform silica gel column chromatography (petroleum ether / ethyl acetate: 2 / 1) to obtain 7.572 g of yellow oily liquid, isolated yield Y=72.11%. Rf (ethyl acetate / petroleum ether: 1 / 1): 0.59.

preparation example 3

[0114] Preparation Example 3: Preparation of Compound I-2 (2-methyl-3-hydroxyl-5-hydroxyl-5-(3',4',5'-trimethoxy)-ethyl valerate)

[0115]

[0116] In an ice-water bath, 3.06 g (9 mmol) of intermediate I-1 was dissolved in tetrahydrofuran (67.5 ml) and methanol (27 ml), and 1.04 g (27 mmol) of sodium borohydride was slowly added to react for 30 minutes. Add 30 ml of saturated ammonium chloride aqueous solution, extract with ether, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, and remove ether by rotary evaporation to obtain 3.22 g of crude product, which is directly carried out to the next reaction. Rf (ethyl acetate / petroleum ether: 1 / 1): 0.35.

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Abstract

The present invention relates to compound with 6-aryl-3-substituted methylene-pyrone structure, derivative with 6-aryl-3-methyl-4-acryloxy tetrahydro pyrone skeleton, and their preparation process and use. Pharmacological activity test shows that the compound possesses acetylcholinesterase inhibiting activity and is expected to be used as medicine for senile dementia. The compound also shows relatively high activity of inhibiting tumor cells of prostate cancer, oral epithelium cancer, lung cancer and cervical cancer and thus is expected to be used as antitumor medicine.

Description

field of invention [0001] The invention belongs to the fields of organic chemistry, medicinal chemistry and pharmacology, in particular, the invention relates to a 6-aryl-3-substituted methylene-pyrone with the functions of preventing and treating senile dementia and organic dementia and cytotoxicity Derivatives and 6-aryl-3-methyl-4-acyloxytetrahydropyrone derivatives and their preparation methods and applications. The pharmacological activity test shows that the compound has the activity of inhibiting acetylcholinesterase, and can be expected to be used as a medicine for preventing and treating senile dementia. This kind of compound also shows the effect on six tumor cells such as prostate cancer cell (PC-3), nasopharyngeal carcinoma cell (CNE), oral epithelial cancer cell line (KB), human lung cancer cell (A549), human liver cancer cell (BEL- 7404), the growth of human cervical cancer cells (Hela) has strong inhibitory activity, and it can be expected to be used as an anti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38A61K31/366A61K9/00A61P25/28A61P35/00
Inventor 赵昱蒋翔锐敖雷白骅巫秀美周长新
Owner 浙江海正集团有限公司
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