Xanthine aromatic acid ether derivatives and application thereof

A xanthine aromatic acid ether and derivative technology, applied in the field of chemistry, can solve the problem of not providing satisfactory therapeutic effects, and achieve the effects of excellent neuroprotective activity, platelet aggregation inhibition, and significant neuroprotective function

Pending Publication Date: 2021-03-16
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Given the complexity of stroke disease, modulating a single target therapy does not appear to provide satisfactory clinical outcomes

Method used

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  • Xanthine aromatic acid ether derivatives and application thereof
  • Xanthine aromatic acid ether derivatives and application thereof
  • Xanthine aromatic acid ether derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Compound 4-(2-(3,7-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)ethoxy)benzoic acid (F -1) synthesis:

[0033]

[0034] Step 1 Add compound 1 (10.0mmol, 1.0eq) and DMSO (30mL) to a 100mL dry round bottom flask, add 60% NaH (15.0mmol, 1.5eq) in batches under stirring at room temperature, and continue stirring for 10min, The compound 1,2-dibromoethane (40.1 mmol, 4.0 eq) was added to the reaction solution, stirred at 60° C. for 6 h, TLC showed that the reaction was almost complete. The reaction solution was diluted with 300 mL of water, extracted with dichloromethane (80 mL×3), washed 3 times with saturated brine, dried over anhydrous sodium sulfate, filtered with suction and concentrated the filtrate under reduced pressure, and the residue was separated by silica gel column to obtain intermediate 2 , as a white solid, yield 45%.

[0035] Step 2 Add intermediate 2 (2.3 mmol, 1.0eq) successively in a 250mL dry round bottom flask, K 2 CO 3 (5.6mmol, 2.4eq) and...

Embodiment 2

[0038] Compound 4-(3-(3,7-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)propoxy)benzoic acid (F -2) Synthesis:

[0039] Referring to the synthesis method of Example 1, the raw material of 1,2-dibromoethane was replaced by the raw material of 1,3-dibromopropane to obtain compound F-2 as a white solid with a yield of 74.8%. ESI-MS[M-H] - : m / z=357.03, 1 H NMR (400MHz, DMSO-d 6 )δppm: 8.01 (s, 1H, N = CH), 7.85 (d, J = 8.8Hz, 2H, ArH), 6.89 (d, J = 8.8 Hz, 2H, ArH), 4.12-4.04 (m, 4H, CH 2 CH 2 CH 2 ),3.84(s,3H,NCH 3 ), 3.39(s,3H,NCH 3 ),2.07-2.00(m,2H,CH 2 CH 2 CH 2 ).

Embodiment 3

[0041] Compound (E)-3-(4-(2-(3,7-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)B Synthesis of oxy)-3-methoxyphenyl)acrylic acid (F-3):

[0042] Referring to the synthesis method of Example 1, the raw material of methyl p-hydroxybenzoate was replaced with the raw material of methyl ferulic acid to obtain compound F-3 as a white solid with a yield of 79.2%. ESI-MS[M-H] - : m / z=399.02, 1 H NMR (400MHz, DMSO-d 6 )δppm: 8.00 (s, 1H, N = CH), 7.44 (d, J = 16.0Hz, 1H, ArCH =), 7.21 (s, 1H, ArH), 7.13 (d, J = 8.3Hz, 1H, ArH ), 6.92(d, J=8.3Hz, 1H, ArH), 6.44(d, J=16.0Hz, 1H,=CH), 4.30(t, J=5.5Hz, 2H, OCH 2 ), 4.21(t, J=5.5Hz, 2H, NCH 2 ),3.84(s,3H,OCH 3 ),3.67 (s,3H,NCH 3 ),3.38(s,3H,NCH 3 ).

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PUM

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Abstract

The invention relates to xanthine aromatic acid ether derivatives and application thereof, and belongs to the technical field of chemistry. The compound (formula I) provided by the invention not onlyhas a significant inhibitory effect on arachidonic acid (AA) and ADP-induced platelet aggregation, but also has a significant neuroprotective function, and part of the compounds show excellent neuroprotective activity. The derivatives can be used for research and development of drugs for nerve injury related diseases, and provides a new approach for research and development of ischemic cerebrovascular disease treatment drugs.

Description

technical field [0001] The invention relates to a class of xanthine aromatic acid ether derivatives and uses thereof, belonging to the technical field of chemistry. Background technique [0002] Stroke is an acute cerebrovascular disease, including hemorrhagic stroke and ischemic stroke, which is characterized by high morbidity, mortality and disability. In recent years, with the increasing aging of the global population, the number of stroke diseases continues to increase. So far, there is still a lack of effective drugs for the prevention and treatment of stroke in clinical practice. Studies have shown that ischemic stroke is a complex pathological cascade reaction involving multiple cytokines and multiple signal transduction. The main mechanism is that blood vessels in the brain are suddenly blocked to form a thrombus in a short period of time, resulting in the formation of a thrombus in the brain and insufficient energy and oxygen supply. This leads to a series of cas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/04A61K31/522A61P25/00A61P25/14A61P25/28A61P25/16A61P25/02A61P3/10A61P21/00A61P9/10A61P25/08
CPCC07D473/04A61P25/00A61P25/14A61P25/28A61P25/16A61P25/02A61P3/10A61P21/00A61P9/10A61P25/08
Inventor 李家明何广卫金凡许勤龙储昭兴王宏伟钱诗虎赵炎
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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