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Novel sulfonyl substituted benzophenone oxide compounds, prepraring method and application thereof

A xanthone and sulfonyl technology, which is applied in the field of xanthone ACAT enzyme inhibitory active compounds, can solve problems such as affecting the normal operation of the body, unreported inhibitory activity, diseases, etc., and achieves regulation of sebaceous gland function and inhibition of sebum. overgenerated effect

Inactive Publication Date: 2008-09-24
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Drugs currently on the market for the treatment of atherosclerosis, such as blood lipid-lowering and anti-platelet drugs, have some defects: first, they block the functions of substances required for normal physiological operations, and long-term use will affect the normal operation of the body
Second, this type of drug will cause greater damage to the liver and kidney function, and long-term use will cause disease
[0006] Compound of the present invention, and its inhibitory activity to ACAT enzyme has not been reported

Method used

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  • Novel sulfonyl substituted benzophenone oxide compounds, prepraring method and application thereof
  • Novel sulfonyl substituted benzophenone oxide compounds, prepraring method and application thereof
  • Novel sulfonyl substituted benzophenone oxide compounds, prepraring method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The target compound was synthesized according to the reaction route (a).

[0053] (1) Preparation of 2,4,5-trimethoxybenzoyl chloride (II)

[0054] Put 250g (1.179mol) of 2,4,5-trimethoxybenzoic acid in a 1000°C three-neck flask, stir at room temperature, slowly add 300ml of thionyl chloride dropwise, and slowly heat to reflux after the dropwise addition, continue React for 4 to 5 hours. After completion of the reaction, 150 ml of toluene was added to the reaction, and the azeotrope of thionyl chloride and toluene was distilled. When no liquid was evaporated, a white-green solid was produced upon cooling, and the crude product was dried under reduced pressure. Recrystallized from methanol to obtain 237g of 2,4,5-trimethoxybenzoyl chloride, yield 87.45%, melting point: 133-138°C.

[0055] (2) Preparation of (2-hydroxyl-4,5-dimethoxyphenyl)-(2,4,6-trimethoxyphenyl)-methanone (IV)

[0056] Put 25g (0.11mol) of 2,4,5-trimethoxybenzoyl chloride and 20g (0.12mmol) of 1,3,...

Embodiment 2

[0066] Synthesize target compound according to reaction synthetic route (b)

[0067] (6) Preparation of N-cyclopropylamine-1-hydroxyl-3,6,7-trimethoxy-4-sulfonamide-xanthone

[0068] Put N-cyclopropylamine-1,3,6,7-tetramethoxy-4-sulfonamide-xanthone 0.218g (0.0005mol) in a 100ml dry three-necked bottle equipped with a thermometer and a stirrer, Add 20ml of acetocyanide, heat the outside to 50°C with an oil bath, slowly add 2g of aluminum trichloride (0.0015mol) under stirring, and continue stirring for 5 hours after the addition is complete. After the reaction was completed, the reaction night was slowly poured into 100ml of 2% hydrochloric acid solution. The solution was extracted four times with 400ml ethyl acetate, and the ethyl acetate extracts were combined and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated to give a crude yellow solid. The crude product was subjected to column chromatography (petroleum ether: ethyl acetate 3:1), and finally N-cyclop...

Embodiment 3

[0069] Example 3 Preparation of 4-(2S,3R)-2,6-dimethylmorphinesulfonyl-1,3,6,7-tetramethoxy-xanthone

[0070] Put 0.55g (0.0013mol) of 1,3,6,7-tetramethoxy-4-sulfonyl chloride-xanthone into 100ml dry eggplant, add 20ml 1,4-dioxane and stir , fully suspend the raw material in 1,4-dioxane, slowly add 100ul (2S,3R)-2,6-dimethylmorphine dropwise at room temperature, and react for 1 hour. After the reaction was completed, the reaction solution was poured into water, extracted with 250ml of dichloromethane four times, the dichloromethane extracts were combined, dried over anhydrous sodium sulfate, and the dichloromethane was distilled off to obtain a yellow solid crude product. The crude product was washed with a small amount of acetone, and there was a white insoluble solid, which was filtered to obtain 4-(2S,3R)-2,6-dimethylmorphinesulfonyl-1,3,6,7-tetramethoxy-xanthene Ketone 0.57g, yield 89.1% Melting point: >250°C.

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Abstract

The present invention relates to the field of medical technology, and in particular relates to a category of novel sulphonyl substituted xanthene ketone compounds that have a structural formula as shown in the right, a preparation method and application thereof. The compound has high inhibitory activity for ACAT1 / ACAT2; most of the compounds have high inhibitory activity for acyl coenzyme A cholesterol acyltransferase (ACAT). The compounds can be used for preparing anti-atherosclerosis drug combination. Furthermore, the compounds can be used as a preventive or a treating agent of such diseases as angina, myocardial infarction, cerebral infarction, apoplexy, Alzheimer's disease, acute coronary syndrome, PTCA or restenosis of coronary artery after a bracket is arranged. The compounds can be used as a treating agent to adjust the function of sebaceous glands of the skin and inhibit the excessive generation of sebum. And the compounds can be used for treating such diseases as acne-like damage caused by oily skin, acne, seborrhea and corticosteroids.

Description

Technical field: [0001] The invention relates to the field of medical technology, in particular to a new class of sulfonyl-substituted xanthone-type ACAT enzyme-inhibiting active compounds, as well as their preparation methods and applications. Background technique: [0002] Atherosclerosis has long been the leading cause of death among residents in developed countries. With the improvement of our people's living standard and the change of diet structure, the disease has become the main cause of death in our country. [0003] Drugs currently on the market for treating atherosclerosis, such as blood lipid-lowering and anti-platelet drugs, have some defects: first, they block the functions of substances required for normal physiological operations, and long-term use will affect the normal operation of the body. Second, this class of drugs will cause greater damage to the liver and kidney functions, and long-term use will cause diseases. [0004] The accumulation of cholester...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86A61K31/352A61P9/10A61P25/28A61P17/08A61P17/10
Inventor 陈万生吴秋业胡宏岗宴菊芳吴玮峰叶飞俞世冲赵庆杰但志刚邹燕徐建明柴晓云
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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