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New substituted cyclohexanone compound, and preparation method and application thereof

A compound, cyclohexanone technology, applied in the preparation of sulfuric acid amide, organic chemistry, drug combination and other directions, can solve the problems of high price and little effect, and achieve the effect of significant activity and broad application prospects.

Inactive Publication Date: 2018-01-19
汕头经济特区鮀滨制药厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the existing drugs for the treatment of Alzheimer's disease, they are expensive and have little effect, and no specific drugs have entered the market for many years

Method used

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  • New substituted cyclohexanone compound, and preparation method and application thereof
  • New substituted cyclohexanone compound, and preparation method and application thereof
  • New substituted cyclohexanone compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 Preparation of substituted cyclohexanone compounds

[0049] The synthetic route is as follows:

[0050]

[0051] Formula (I) 1,13-sulfonamido palitantin

[0052] 1. Preparation of compound 1 (13-hydroxypalitantin)

[0053] (1) Prepare seed culture medium: 200g potato, 20g glucose, 1L tap water, dispense equally into 4 500mL conical flasks, sterilize at 121°C for 30 minutes.

[0054] (2) Cultivation of seeds: The SYSU-HQ3 strain of marine fungus was connected to a seed culture medium, and cultured on a shaker at a rotation speed of 120 rpm for 72 hours at a temperature of 28° C. to obtain a seed culture solution.

[0055] (3) Preparation of fermentation medium: 6000g wheat medium, 180g sea salt, 6L tap water, sterilized at 121°C for 30 minutes.

[0056] (4) Fermentation culture: In an aseptic environment, 5 mL of the seed culture solution was put into a conical flask containing a fermentation medium, and the culture was allowed to stand at 25°C for 28 days to obtain a ferm...

Embodiment 2

[0068] Example 2 Acetylcholinesterase inhibitory activity experiment

[0069] Experiments on the inhibitory activity of compound 1 (13-hydroxypalitantin) in Example 1 and compound 1,13-sulfonamidopalitantin of formula (I) on acetylcholinesterase:

[0070] 1. Material:

[0071] Substrate: 3mg / ml thioacetylcholine iodized salt (ATOH);

[0072] Chromogenic agent: 4mg / ml 5,5'-dithiobis(2-nitrobenzoic acid) (DTNB);

[0073] Buffer: 0.01M dipotassium hydrogen phosphate-potassium dihydrogen phosphate buffer (pH=7.0);

[0074] Enzyme: prepare 2u / ml acetylcholinesterase solution;

[0075] Positive control compound: Huperzine A

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Abstract

The invention relates to a substituted cyclohexanone compound with the structure as shown in a formula (I), and a preparation method thereof. The preparation method comprises the following steps: a, performing reaction on a compound 1 and a hydroxyl protective agent under the existence of acid to obtain a compound 2 with 4,5-position hydroxyl protected by acetonylidene; b, performing reaction on the compound 2 and sulfonyl chloride under the existence of alkali to obtain a compound 3; c, performing reaction on the compound 3 and ammonium carbonate to obtain a compound 4; and d, performing acetonylidene deprotection on the compound 4 under the existence of acid to obtain the substituted cyclohexanone compound. The substituted cyclohexanone compound has remarkable activity on acetylcholin esterase, the activity is obviously more excellent than that of a positive medicine huperzine A, and the substituted cyclohexanone compound can be used for preparing medicines for treating Alzheimer's disease. The structural formulas of the compound of the formula (I), the compound 1, the compound 2, the compound 3 and the compound 4 are as shown in the description.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a new substituted cyclohexanone compound and its preparation method and application. Background technique [0002] Alzheimer's disease is a systemic neurodegenerative disease of the cerebral cortex that occurs frequently in the elderly and has multiple causes. The clinical manifestations mainly include progressive memory disorders, movement disorders, and cognitive disorders. [0003] The international research and development of drugs for the treatment of Alzheimer's disease has not stopped, but no new drugs have been introduced for more than 10 years. If a new drug can alleviate or treat this disease, it will be a major contribution to mankind. Among the existing drugs for the treatment of Alzheimer's disease, they are expensive and have little effect, and no specific drugs have entered the market for many years. The high incidence of Alzheimer's disease caused by entering ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/34C07C307/02C12P7/26A61K31/18A61P25/28
Inventor 黄锡山冯汝华黄中书黄铁强王丽张俊珺
Owner 汕头经济特区鮀滨制药厂