A kind of 8-amino-4,6-diyn-1-alcohol compound and its preparation method and application

A technology of compounds and alcohols, which is applied in the field of 8-amino-4,6-diyn-1-ols and their preparation, and can solve problems such as easy recurrence

Inactive Publication Date: 2019-04-02
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many patients are only partially relieved by these antidepressants and are prone to relapse, therefore, there is an urgent need to explore novel scaffolds as potential antidepressant drug candidates to improve the efficacy of existing treatments for depression

Method used

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  • A kind of 8-amino-4,6-diyn-1-alcohol compound and its preparation method and application
  • A kind of 8-amino-4,6-diyn-1-alcohol compound and its preparation method and application
  • A kind of 8-amino-4,6-diyn-1-alcohol compound and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0021]

[0022] 1, the preparation of (Z)-8-((tert-butyldiphenylsilyl)oxy)-N,N-diethyl-6-octene-2,4-diyn-1-amine ( 3a)

[0023] Take a 10mL round-bottomed flask, dissolve 22.5μL (0.16mmol) of 3-diethylamino-1 propyne and 5.9mg (0.03mmol) of cuprous iodide in 0.6mL of piperidine under the protection of argon, and place in an ice-water bath Cool to 0°C, slowly drop (Z)-(5-bromo-2-penten-4-yne-1-oxyl)tert-butyldiphenylsilane 50mg (0.13mmol) in 0.2 mL of the solution formed by piperidine, after the addition, slowly warm up to room temperature, react at room temperature for 4h, add 0.5mL of saturated ammonium chloride solution to terminate the reaction, then extract with ethyl acetate (0.3mL x 2), combine organic phase, washed with saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure, using V (petroleum ether): V (ethyl acetate) = 2:1 as the eluent, silica gel column chromatography to obtain light yellow ...

Embodiment 2

[0040] Corticosterone-injured PC12 cell protection experiment:

[0041] This experiment proves that the compound (Z)-8-(diethylamino)-2-octene-4,6-diyn-1-ol has a protective effect on PC12 cells damaged by corticosterone, and the specific operations are as follows:

[0042] Cell viability was determined by MTT assay. PC12 cells (2×104 per well) were inoculated in 96-well culture plates, respectively coated with polylysine (0.01%), and after culturing for 24 h, PC12 cells were treated with corticosterone (400 μmol L -1 ) and corticosterone (400μmol·L -1 ) plus different concentrations of (Z)-8-(diethylamino)-2-octene-4,6-diyn-1-ol (0.1,1,10,20,50,100μmolL -1 ), incubated after 24h, 10μL 3-(4,5-dimethylthiazole-2)(4,dimethylthiazole-2)2,5-diphenyltetrazolium bromide (5mg·mL -1 ) was added to each well, and after incubation at 37° C. for 4 hours, the culture solution was taken out, and the absorbance was measured with a microplate reader at a wavelength of 570 nm. Cell viabilit...

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Abstract

The invention belongs to the technical field of medicine chemistry, and particularly relates to an 8-amido-4,6-diyne-1-alcohol compound, and a preparation method and application thereof. The preparation method of the 8-amido-4,6-diyne-1-alcohol compound comprises the following steps that (Z)-(5-bromopentyl-2-alkene-4-propynyloxy) tert-butyldiphenylsilane and terminal alkyne compounds take Cardiot-Chodkiewicz coupling reaction to produce (Z)-8-((tert-biphenyl silicyl)oxyl)-6-octadien-2,4-diyne-1-disubstituted amine; then, protection removal is performed under the effect of triethylamine hydrofluoride to obtain (Z)-8-(disubstituted amino)-2-octadien-4,6-diyne-1-alcohol, wherein the R1 represents CH3(CH2)n; the R2 represents CH2(CH2)n; n is 0 to 6.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an 8-amino-4,6-diyn-1-alcohol compound and a preparation method and application thereof. Background technique [0002] Depression is a common mental illness with high morbidity and mortality. Most existing antidepressants work by increasing the levels of monoamine neurotransmitters (serotonin levels (5-HT), norepinephrine (NE), and dopamine (DA)). However, many patients can only partially relieve symptoms after using these antidepressants and are prone to relapse. Therefore, there is an urgent need to explore novel scaffolds as potential antidepressant drug candidates to improve the efficacy of existing treatments for depression. The PC12 cell line, derived from rat adrenal medullary pheochromocytoma, is widely used as a model system to study various neurological functions. In addition, studies have shown that different antidepressants can have a protect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/24C07C213/08A61P25/24
CPCY02P20/55
Inventor 马开庆任虎斌周玉枝高晓霞秦雪梅张丽增
Owner SHANXI UNIV
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