Synthesis method and application of S-allyl-L-cysteine substituted tyrosol derivative with neuroprotective activity

A technology of cysteine ​​and derivatives, applied in the field of medicinal chemistry, can solve the problems of limiting tyrosol application, low bioavailability, unstable absorption, etc., and achieve the goal of improving mitochondrial function, improving glucose metabolism, and inhibiting cell apoptosis Effect

Inactive Publication Date: 2020-11-20
深圳红景堂生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, problems such as instability and slow absorption in physiological ...

Method used

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  • Synthesis method and application of S-allyl-L-cysteine substituted tyrosol derivative with neuroprotective activity
  • Synthesis method and application of S-allyl-L-cysteine substituted tyrosol derivative with neuroprotective activity
  • Synthesis method and application of S-allyl-L-cysteine substituted tyrosol derivative with neuroprotective activity

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation process of compounds SAO-1~SAO-8, SAO-9~SAO-16.

[0038] Synthesis of compound 1-1

[0039]

[0040] Compound 1-0 (16.1g, 100mmol) was weighed and dissolved in tetrahydrofuran (100ml), di-tert-butyl dicarbonate (21.8g, 100mmol) and saturated sodium bicarbonate solution (250ml) were added successively, and stirred at room temperature for 5 hours. After the reaction, the pH was adjusted to acidic with dilute hydrochloric acid (1 mol / L), then extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain product 1-1 (22.2 g, 85%). MS(ESI)m / z:260.1[M-H] - .

[0041] Synthesis of Compound 1-2

[0042]

[0043] Under nitrogen protection, compound 1-1 (2.61g, 10mmol), triphenylphosphine (2.62g, 10mmol), tyrosol (1.38g, 10mmol) were dissolved in anhydrous tetrahydrofuran (40ml), and added dropwise under ice-bath conditions Diisopropyl azodicarboxylate (2.02g, 10mmol) was reacted at room tempera...

Embodiment 2

[0114] Activity evaluation experiment of the compound of the present invention

[0115] After Alzheimer's disease transgenic mice (3xTg-AD, 8 months old) were treated with compound SAO-1 (5.0mg / kg and 20.0mg / kg) for 4 weeks, behavioral tests found that the synthetic representative small molecule compound SAO-1 can significantly improve the platform latency of mice (A) and reduce the number of platform mistakes (B), and the effect is more obvious than the positive control drug memantine (5.0mg / kg), suggesting that SAO-1 can significantly Improved spatial memory in Alzheimer's disease transgenic mice.

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Abstract

The invention discloses a synthesis method of an S-allyl-L-cysteine substituted tyrosol derivative with neuroprotective activity, and application of the S-allyl-L-cysteine substituted tyrosol derivative. According to the invention, the compound comprises a tyrosol analogue parent nucleus and a substituent group containing an S-allyl-L-cysteine structure, wherein X can be O, S or NH, R1 is selectedfrom H, alkyl or alkyl acyl, R2 is selected from H, alkyl, acyl or carbamate, and R3 is selected from H, halogen, hydroxyl or alkoxy; and the compound has multiple action mechanisms, has the effectsof resisting oxidation, resisting inflammation, improving mitochondrial functions, improving glycometabolism, promoting nerve cell regeneration, inhibiting cell apoptosis and the like, and has extremely high medicinal value when being applied to senescence and neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and more specifically relates to a synthesis method and application of S-allyl-L-cysteine-substituted tyrosol derivatives with neuroprotective activity, including aging and neurodegenerative diseases Wait. Background technique [0002] Neurodegenerative diseases (Neurodegenerative diseases, ND) are chronic diseases that lead to the gradual death of neurons, including Alzheimer's disease, Parkinson's disease and Huntington's disease, which often bring great pain and suffering to patients and families. burden. With the aging of the population, it is expected that by 2040, ND will replace cancer and become the second largest type of disease that causes human death. However, there is currently no drug in the world that can effectively treat neurodegenerative diseases. [0003] The pathology of neurodegenerative diseases ND is closely related to oxidative stress, mitochondrial dysfunction, Ca2+ in...

Claims

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Application Information

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IPC IPC(8): C07C323/58C07C323/59C07C319/20A61K31/222A61K31/27A61P25/28A61P39/06A61P25/14A61P25/16A61P29/00A61P3/00
CPCA61P3/00A61P25/14A61P25/16A61P25/28A61P29/00A61P39/06C07B2200/07C07C323/58C07C323/59
Inventor 李鸣沈圆圆
Owner 深圳红景堂生物医药科技有限公司
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