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A kind of optically active xanthamide ketone derivative and its application

A kind of xanthinone and optically active technology, which is applied in the field of biomedicine, can solve the problems of further research and development, untargeted research results on the structure or type of symptomatic compounds, etc., so as to reduce nerve cell damage and have a novel structure , the effect of simple process

Active Publication Date: 2022-04-05
GUANGDONG PHARMA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, there is still a large research gap in the research and application of pampidamide compounds in anti-AD, Parkinson's disease, cerebral apoplexy, traumatic brain injury and other diseases, and there are no targeted research results on the structure or type of symptomatic compounds. Subject to further research and development

Method used

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  • A kind of optically active xanthamide ketone derivative and its application
  • A kind of optically active xanthamide ketone derivative and its application
  • A kind of optically active xanthamide ketone derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The preparation of embodiment 1 (-)-bantamide ketone or (+)-bantamide ketone

[0078] The preparation process of (-)-bantamide ketone or (+)-bantamide ketone is as follows:

[0079] 1. Synthesis and resolution of racemic epoxy cinnamic acid ((±)-β-phenylglycidyl acid):

[0080]

[0081] ①Synthesis of racemic epoxy cinnamic acid ((±)-β-phenylglycidyl acid)

[0082]Weigh 148.20g of trans-cinnamic acid, dissolve it in 650mL of acetone, add 380.0g of sodium bicarbonate under stirring, cool to 0-20°C in an ice bath, add 650mL of water, then add 620.0g of potassium persulfate in 1250mL of aqueous solution, keep The temperature is lower than 20°C. After reacting for 3 hours, filter out insoluble salts, add 1.0L ethyl acetate to the filtrate and stir, adjust the pH to 5-6 with concentrated hydrochloric acid, separate the organic layer, and extract the aqueous layer with 3×500mL ethyl acetate , the organic layers were combined, washed with 1L of distilled water and 1L of sa...

Embodiment 2

[0097] The preparation of embodiment 2 compound (+)-58 and (-)-58

[0098] 1. Preparation of (-)-58:

[0099]

[0100] Weigh 0.590g (2mmol) (-)-Panthamide ketone, 1.150g (6mmol) DCC (dicyclohexylcarbodiimide) and 0.049g (0.4mmol) DMAP (4-dimethylaminopyridine) dissolved in 50mL Dichloromethane, add 6mmol p-trifluoromethylbenzoic acid under stirring at room temperature, TLC monitoring (EA:PE=2:1), after the reaction is complete, successively add 30mL 1M HCl, 30mL saturated sodium bicarbonate and 30mL saturated sodium chloride The solution was washed, dried over anhydrous sodium sulfate, the desiccant was filtered off, and the solvent was spinned off to obtain a crude product, which was subjected to column chromatography and recrystallized from methanol to obtain compound (-)-58, white crystal; yield: 0.748g (80.1%); m.p.131.5 -132.0°C; (c 0.2, CH 3 OH); 1 H NMR (500MHz, Chloroform-d) δ8.18–8.13(m,2H),7.70–7.64(m,2H),7.59–7.53(m,2H),7.48–7.41(m,1H),7.32–7.23 (m,2H),7.21...

Embodiment 3

[0105] The preparation of embodiment 3 compound (+)-58-1 and (-)-58-1

[0106] (-)-58-1:

[0107]

[0108] White needle-like crystals; yield: 0.508g (75.4%); m.p.176.3-177.1℃; (c 0.2, CH 3 OH); 1 H NMR (500MHz, Chloroform-d) δ7.55–7.49(m,2H),7.42(ddt,J=8.7,7.1,1.2Hz,1H),7.31–7.22(m,2H),7.15–7.10(m ,2H),7.10–6.98(m,3H),6.18–6.12(m,1H),5.44(d,J=8.8Hz,1H),4.03(dd,J=9.8,8.9Hz,1H),2.90( d,J=0.6Hz,3H),2.09(s,3H); 13 C NMR (126MHz, Chloroform-d) δ197.17, 171.03, 169.99, 136.46, 133.75, 133.38, 128.78, 128.76, 128.55, 128.26, 72.21, 64.88, 49.16, 29.95, 21.02; HRMS ([ESI): m / z 1] + Calculated 338.1387Found 338.1389; The enantiomeric excess was determined to be 99.9% by HPLC with a Daicel Chiralcel AD-H column (4.6mm×25cm) (n-hexane / i-PrOH=80 / 20, λ=254nm, 1mL / min) ,t=9.4min.

[0109] (+)-58-1:

[0110]

[0111] White needle-like crystals; yield: 0.494g (73.4%); m.p.178.1-179.3°C; (c0.2, CH 3 OH); 1 H NMR (500MHz, Chloroform-d) δ7.55–7.49(m,2H),7.46–7.39(m,1H),7.29–7...

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Abstract

The invention discloses an optically active xanthamidone derivative and its application. The structure of the compound is shown in formula (I); wherein, the R is C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl or ‑COR 1 ; the R 1 from C 1 ~C 4 Substituted or unsubstituted alkane, C 1 ~C 4 Substituted or unsubstituted alkenyl, substituted or unsubstituted phenyl or heterocyclic aromatic ring; the R 1 The substituents in are phenyl, halogenated phenyl, C 1 ~C 4 Alkyl substituted phenyl, C 1 ~C 4 Alkyl halide substituted phenyl, naphthoxy, pyridine or thiophene. The compound of the present invention has novel structure, has a good protective effect on glutamate-induced cerebellar granule nerve cell damage and cerebral ischemia-induced nerve cell or tissue damage, and can be used as a nerve cell protective agent to reduce glutamate or Oxygen-glucose deprivation causes damage to nerve cells, thereby preventing and / or treating neurodegenerative diseases caused by it, such as stroke, traumatic brain injury, Alzheimer's disease and other diseases.

Description

technical field [0001] The invention relates to the technical field of biomedicine, and more specifically, to an optically active xanthinone derivative and its application. Background technique [0002] Glutamate is the main excitatory neurotransmitter in the central nervous system, involved in a variety of physiological functions, such as fast synaptic transmission, neuronal plasticity, learning and memory, etc. Excess glutamate activates the N-methyl-D-aspartate receptor (NMDAR), resulting in excess Ca 2+ Influx, resulting in damage to mitochondrial function, rapid increase in reactive oxygen species (reactive oxygen species, ROS), neurotoxicity, and eventually lead to neuronal cell death. The mechanism of nerve cell damage caused by excessive glutamate plays an important role in the occurrence and development of various brain diseases, such as neurodegenerative diseases, especially stroke, traumatic brain injury, Alzheimer's disease and other diseases. [0003] Ischemic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/273A61P25/28A61P25/00A61P9/10
CPCA61P9/10A61P25/00A61P25/16A61P25/28C07D207/273
Inventor 林汉森庞涛米俊儒徐亚洲许敬梓罗旭娜方成乔张陆勇
Owner GUANGDONG PHARMA UNIV
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