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Steroid sapogenin derivative as well as preparation method and application thereof

A compound, unsubstituted technology, applied in the field of medicinal chemistry, which can solve the problems of reduced mitochondrial redox activity, damage, and high content

Active Publication Date: 2020-10-27
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

ROS and RNS can activate amyloid precursor protein (APP) to secrete β-amyloid (Aβ). Studies have found that the aggregation of Aβ reduces the redox activity of mitochondria, leading to the accumulation of ROS and RNS.
Subsequent studies have shown that Aβ can also interact with catalase in the brain, impairing this enzyme to clear H 2 o 2 capability, resulting in the H 2 o 2 high content

Method used

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  • Steroid sapogenin derivative as well as preparation method and application thereof
  • Steroid sapogenin derivative as well as preparation method and application thereof
  • Steroid sapogenin derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] The synthesis of compound F is as follows:

[0132]

[0133] Synthesis of Intermediate D1:

[0134] Dissolve diosgenin (2mmol), aluminum isopropoxide (3mmol) and cyclohexanone (3mmol) in 20mL toluene, react at 95°C for 4h, use after the reaction is complete, spin evaporate toluene to dryness, dichloromethane / water extraction, The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure and subjected to column chromatography (ethyl acetate / petroleum ether=1:15) to obtain compound D1 (80%).

[0135] Synthesis of Intermediate D2:

[0136] Dissolve compound D1 (1.5mmol) in 15mL of dioxane, add trimethylchlorosilane at low temperature, add 2,3-dichloro-5,6-dicyano-p-benzoquinone (3mmol) after 15min to react for 12h, and react After complete use, the solvent was evaporated to dryness, extracted with dichloromethane / water, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressur...

Embodiment 2

[0140] The preparation of compound F1-F11 is shown in the following reaction formula

[0141]

[0142] in, express

[0143] Preparation of Compounds F1~F11

[0144] Compound F (396mg, 1mmol), the corresponding carboxylic acid (1.2mmol), EDCl (1.2mmol), DMAP (0.05mmol) were dissolved in 20mL of dichloromethane under the protection of argon, and reacted at room temperature for 3h. After the reaction was completed, quenched with 30 mL of water, extracted with dichloromethane (3*30 mL), combined the organic phases, dried over anhydrous sodium sulfate, concentrated under reduced pressure and then subjected to column chromatography (ethyl acetate / petroleum ether=1: 20) Obtain compounds F1-F11 (75%-85%).

[0145] Compound F1, white solid. 1 H NMR (400MHz, CDCl 3 )δ7.27 (1H, d, J = 8.3Hz), 6.83 (1H, dd, J = 8.4Hz, 2.5Hz), 6.79 (1H, d, J = 2.3Hz), 4.46 (1H, m), 3.49 (1H,dd,J=9.9Hz,5.0Hz),3.39(1H,t,J=10.9Hz),2.88(2H,m),2.28(3H,s),1.00(3H,d,J=6.8Hz ),0.81(3H,s),0.80(3H,d,J=6...

Embodiment 3

[0157] Preparation of Compounds F12~F15

[0158]

[0159] in, express

[0160] Preparation of Compounds F12~F15

[0161] Compound F (396mg, 1mmol), the corresponding sulfonyl chloride (1.2mmol), TEA (1.2mmol) were dissolved in 20mL of dichloromethane under the protection of argon, and reacted at room temperature for 3h. After the reaction was completed, quenched with 30 mL of water, extracted with dichloromethane (3*30 mL), combined the organic phases, dried over anhydrous sodium sulfate, concentrated under reduced pressure and then subjected to column chromatography (ethyl acetate / petroleum ether=1: 20) Obtain compounds F12-F15 (80%-90%).

[0162] Compound F12, white solid. 1 H NMR (400MHz, CDCl 3 )δ7.23 (1H, d, J = 8.5Hz), 7.01 (1H, d, J = 8.5Hz), 6.98 (1H, s), 4.46 (1H, dd, J = 13.9Hz, 7.8Hz), 4.46 (1H,dd,J=13.9Hz,7.8Hz),3.49(1H,dd,J=9.8Hz,4.7Hz),3.39(1H,t,J=10.9Hz),2.89(2H,m),1.00( 3H,d,J=6.7Hz),0.82(3H,s),0.80(3H,d,J=6.4Hz).C 28 h 40 o 5 S MS(EI):m / z 489.3...

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Abstract

The invention discloses a steroid sapogenin derivative represented by general formula (1), and a pharmaceutically acceptable salt and a pharmaceutical composition thereof. The steroid sapogenin derivative disclosed by the invention has a protective effect on neurons, and also has anti-inflammatory and antioxidant effects and an acetylcholin esterase inhibition effect, so that the steroid sapogeninderivative can be used for treating cholinesterase inhibition, oxidative stress and inflammation-related diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry; specifically, the invention relates to a steroidal sapogenin derivative, a pharmaceutical composition containing the derivative and application thereof. Background technique [0002] Under normal physiological conditions, there is an efficient oxidation-reduction system in cells to regulate the concentration of highly active substances, so as to prevent oxidative damage caused by excessive oxidation levels. For example, when hydrogen peroxide is produced, the body will secrete a certain concentration of catalase and glutathione peroxidase to promote its metabolism, but under pathological conditions, the balance of this oxidation-reduction system will be disrupted. break down, resulting in oxidative stress damage to the body. Studies have shown that high-level and long-term oxidative stress levels directly lead to tissue damage by causing intracellular redox system imbalance on the one hand, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61P25/00A61P25/28A61P25/16A61P25/18A61P25/24A61P35/00A61P9/12A61P29/00A61P25/30
CPCC07J71/0005A61P25/00A61P25/28A61P25/16A61P25/18A61P25/24A61P35/00A61P9/12A61P29/00A61P25/30Y02P20/55
Inventor 马磊王蕊杨桂香李洁李诗良付建军范文康章立苏琳
Owner EAST CHINA UNIV OF SCI & TECH
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