Conjugated dialkynediol compounds and application thereof

A technology of conjugated diacetylenic diols and compounds, applied in organic chemistry, drug combination, nervous system diseases, etc., can solve problems such as failure to protect nerve cells, PC12 cell damage, etc.

Inactive Publication Date: 2016-11-16
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2016, the inventors applied for a general, simple and effective total synthesis method of Bupleinol (1) and its analogue RB-2 (2), obtaining a certain amount of natural product, and then in the injury of PC12 cells by corticosteroids. In the protection experiment, it was proved that RB-2 did not protect nerve cells, on the contrary, it still had a certain damage effect on PC12 cells

Method used

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  • Conjugated dialkynediol compounds and application thereof
  • Conjugated dialkynediol compounds and application thereof
  • Conjugated dialkynediol compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (Z)-(tert-butyldiphenylsilyl)oxy)-7-nonen-3,5-diyn-1-ol (S01-02), the structure is as follows:

[0039]

[0040] The specific preparation method is:

[0041] 1.1 Take a 10mL round bottom flask, dissolve 12.3μL (0.16mmol) of 3-butyn-1-ol and 5.9mg (0.03mmol) of cuprous iodide in 0.6mL of piperidine under the protection of argon, and put it in an ice-water bath Cool to 0°C, slowly drop (Z)-((5-bromo-2-penten-4-yne-1-oxyl)(tert-butyl)diphenylsilane 50mg (0.13mmol) dropwise at this temperature Dissolve in 0.2mL of piperidine to form a solution, after 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, and then extract with ethyl acetate (0.3mL×2) , combine the organic phases, wash with saturated NaCl solution, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure, use V (petroleum ether): V (ethyl acetate) = 2:1 as eluent, silica gel...

Embodiment 2

[0052] Example 2 (2Z,8E)-2,8-decadiene-4,6-diyne-1,10-diol (S02-02), the structure is as follows:

[0053]

[0054] The specific preparation method is:

[0055] 2.1 Replace the 3-butyn-1-ol in Step 1.1 of Example 1 with (E)-2-penten-4-yn-1-ol, and the remaining raw material reagents and preparation methods are the same as in Example 1.1 to obtain Product (2E,8Z)-10-((tert-butyldiphenyl)oxy)-2,8-decadien-4,6-diyn-1-ol (S02-01). Colorless oily liquid, yield 36%.

[0056] In order to further prove that (2E,8Z)-10-((tert-butyldiphenyl)oxy)-2,8-decadiene-4,6-diyn-1-ol (S02-01 ), carried out nuclear magnetic resonance detection to it, obtained proton nuclear magnetic resonance spectrum and carbon spectrum, see respectively Figure 5 with Image 6 , the specific test results are as follows:

[0057] 1 H NMR (600MHz, CDCl 3 )δ:7.69-7.68(m,4H),7.44-7.39(m,6H),6.41-6.37(m,1H),6.24-6.21(m,1H),5.84(d,J=15.6Hz,1H) ,5.55(d,J=11.4Hz,1H),4.48(d,J=6.0Hz,2H),4.25(d,J=4.2Hz,2H),1.26(s...

Embodiment 3

[0066] Example 3. (Z)-7-(4-(hydroxymethyl)phenyl)-2-heptene-4,6-diyn-1-ol (S03-02), the structure is as follows:

[0067]

[0068] The specific preparation method is:

[0069] 3.1 Replace 3-butyn-1-alcohol in Step 1.1 of Example 1 with 4-ethynyl benzyl alcohol, and the remaining raw material reagents and preparation methods are the same as in Example 1.1 to obtain (Z)-(4-(7- ((tert-butyldiphenyl)oxy)-5-heptene-1,3-diyne-benzyl alcohol (S03-01), light yellow oily liquid, yield 70%.

[0070] In order to further prove (Z)-(4-(7-((tert-butyldiphenyl)oxy)-5-heptene-1,3-diyne-benzyl alcohol (S03-01) in this example, Carried out nuclear magnetic resonance detection to it, obtained proton nuclear magnetic resonance spectrum and carbon spectrum, see respectively Figure 9 with Figure 10 , the specific test results are as follows:

[0071] 1 H NMR (600MHz, CDCl 3 )δ: 7.69-7.68(m, J=7.8Hz, 4H), 7.47(d, J=7.8Hz, 2H), 7.44-7.39(m, 6H), 7.33(d, J=7.8Hz, 2H), 6.27-6.23(m,1H),5.59(...

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Abstract

The invention belongs to the technical field of medicinal chemistry, particularly relates to conjugated dialkynediol compounds and an application thereof and aims to provide conjugated dialkynediol compounds having a protection function on nerve cells. The compounds have a protection function on corticosterone injured PC12 cells. The conjugated dialkynediol compounds have the following general structural formula shown in the specification, wherein R1 represents -(CH2)N-, and n ranges from 2 to 8; -CH=CH-(CH2)m-, m ranges from 1 to 8; in -phenyl (CH2)o-(o-, meta-, p-), o ranges from 1 to 8.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a conjugated diacetylene glycol compound and its application. Background technique [0002] Depression is a common mental illness characterized by high morbidity, relapse and disability [1] . Its harm has attracted more and more attention from the medical and health circles in the world. However, the clinical curative effect of the existing antidepressant western medicine is not satisfactory, and there are still problems such as narrow antidepressant spectrum, large side effects, slow onset of effect, easy recurrence and high drug price, so the development of a new generation of antidepressant drugs is a research hotspot. [0003] The pathogenesis of depression is still unclear. In recent years, a large number of experiments and clinical observations have shown that atrophy or destruction of hippocampal neurons may be the pathogenesis of depression (Fuch...

Claims

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Application Information

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IPC IPC(8): C07C33/048C07C33/30A61P25/16A61P25/24A61P25/28A61P35/00
CPCC07C33/048C07C33/30
Inventor 马开庆苗延红周玉枝李肖秦雪梅张丽增
Owner SHANXI UNIV
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