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Diarylethene compound as well as medicine composition and application thereof

A technology of diarylethene and compound, which is applied in the field of medicine and achieves the effects of small side effects, chemical ease and novel structure

Active Publication Date: 2019-10-29
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, MAO-B inhibitors with high safety have not been approved for clinical treatment in my country

Method used

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  • Diarylethene compound as well as medicine composition and application thereof
  • Diarylethene compound as well as medicine composition and application thereof
  • Diarylethene compound as well as medicine composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Part of the diarylethene compounds of the present invention are purchased from Holland specs company (website: http: / / www.specs.com), and the corresponding numbers of the diarylene compounds in the library are as shown in Table 1:

[0058] Table 1 is the corresponding number of some diarylethene compounds in the library

[0059] compound Numbering compound Numbering compound Numbering 66 AO-289 / 25117029 75 AB-131 / 06806028 93 AJ-291 / 34003011 67 AM-814 / 41094729 76 AA-516 / 12432405 94 AG-777 / 36178018 68 AB-131 / 42301429 78 AG-690 / 37079203 103 AA-504 / 06813049 69 AB-131 / 42300921 80 AN-970 / 40920809 107 AT-051 / 43422454 70 AB-131 / 42300746 82 AB-131 / 42302837 108 AE-641 / 02580034 71 AB-131 / 40897212 84 AI-211 / 09901015 114 AG-664 / 02670043 72 AB-131 / 40897213 85 AG-690 / 11665343 116 AE-641 / 01920053 73 AB-131 / 40897214 88 AG-690 / 12135048 117 AE-641 / 02517058 74 AB-131 / 4089...

Embodiment 2

[0061] This example mainly provides the preparation method of compound 83 and the structure determination data of compound 83.

[0062] The English name of compound 83 is as follows:

[0063] (Z)-2-(4-chlorophenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile

[0064] The preparation method of compound 83 is as follows:

[0065]

[0066] Specific preparation steps: add 455mg p-chlorophenylacetonitrile, 0.41mL p-trifluoromethylbenzaldehyde and 21mg sodium ethoxide to 10mL methanol, stir at room temperature for 2 hours, filter to obtain a white solid, wash twice with 2mL low-temperature ethanol, and dry to obtain 349mg Compound 83 (38% yield).

[0067] The structure determination data of compound 83 are as follows:

[0068] 1 H NMR (400MHz, CDCl 3 )δ7.97(d, J=8.0Hz, 2H), 7.74(d, J=8.0Hz, 2H), 7.63(d, J=8.8Hz, 2H), 7.55(s, 1H), 7.45(d, J=8.8Hz, 2H).

Embodiment 3

[0070] This example mainly provides the preparation method of compound 144 and the structure determination data of compound 144.

[0071] The English name of compound 144 is as follows:

[0072] (Z)-2-(4-chlorophenyl)-3-[6-(trifluoromethyl)-3-pyridyl]prop-2-enenitrile

[0073] The preparation method of compound 144 is as follows:

[0074]

[0075] Specific preparation steps: just replace the reaction raw material in the preparation step of compound 83: p-trifluoromethylbenzaldehyde with 6-(trifluoromethyl)pyridine-3-carbaldehyde.

[0076] The structure determination data of compound 144 are as follows:

[0077] 1 H NMR (400MHz, CDCl 3 )δ8.94(s,1H),8.62(d,J=8.4Hz,1H),7.82(d,J=8.4Hz,1H),7.66(d,J=8.8Hz,2H),7.56(s, 1H), 7.48 (d, J=8.8Hz, 2H).

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Abstract

The invention discloses a diarylethene compound as well as a medicine composition and application thereof and relates to the technical field of medicines. The invention provides the diarylethene compound, and the structural formula (I) of the diarylethene compound is shown in the specification. The diarylethene compound disclosed by the invention has a remarkable monoamine oxidase B (MAO-B) inhibition function, and can be used for preparing monoamine oxidase inhibitors B and Parkinson's disease prevention medicines. The invention further provides the medicine composition with the diarylethenecompound as an active component. The medicine composition can be used as a monoamine oxidase B (MAO-B) inhibitor and a Parkinson's disease treatment medicine. In addition, the diarylethene compound disclosed by the invention is novel in structure, easy in chemical synthesis, low in cost and small in side effect.

Description

technical field [0001] The invention relates to a technical field of medicine, in particular to a diarylethene compound, a pharmaceutical composition with them as active ingredients, and their use in the preparation of monoamine oxidase B (Monoamine Oxidase B, MAO-B) inhibitors and in Application in preparation of medicine for treating Parkinson's Disease (PD). Background technique [0002] Parkinson's disease (PD) is a common neurodegenerative disease with an average age of onset of about 60 years old, which seriously endangers the health of the elderly and has a huge impact on society and economy. The main pathological change of Parkinson's disease is the degeneration and death of dopamine (DA) neurons in the substantia nigra of the basal ganglia, which leads to a significant decrease in the content of DA in the striatum and causes the disease. [0003] Monoamine Oxidase (MAO) is an enzyme that catalyzes the oxidative deamination reaction of monoamines in the human body, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/35C07D213/57C07D409/06C07D405/06A61K31/277A61K31/44A61K31/4436A61K31/443A61K31/444A61P25/16
CPCC07C255/35C07D213/57C07D405/06C07D409/06Y02P20/55
Inventor 左之利孙威孔德信彭佳乐
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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