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Ligustrazine-based chalcone-containing aryloxyalkanoic acid compound, preparation method and application thereof

A compound and composition technology, applied in the field of treating hyperlipidemia, atherosclerosis, containing ligustrazine-based chalcone aryloxyalkanoic acid compounds, can solve problems such as liver damage and high price

Active Publication Date: 2017-10-10
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the drugs commonly used in the clinical treatment of hyperlipidemia mainly include fibrates and statins. Although these drugs have obvious effects in regulating blood lipids, they are expensive and easily cause liver damage.

Method used

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  • Ligustrazine-based chalcone-containing aryloxyalkanoic acid compound, preparation method and application thereof
  • Ligustrazine-based chalcone-containing aryloxyalkanoic acid compound, preparation method and application thereof
  • Ligustrazine-based chalcone-containing aryloxyalkanoic acid compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of (E)-2-ethyl-(4-(3-(3,5,6-trimethylpyrazin-2-yl)acryloyl)phenoxy)acetate (YA1) Preparation 1.12 Synthesis of -Hydroxymethyl-3,5,6-trimethylpyrazine

[0033]

[0034] reaction steps

[0035] In the 250mL three-necked flask, add ligustrazine (15.0g, 0.1mol) successively, 30%H 2 o 2 Solution (24mL, 0.2mol), 15mL of glacial acetic acid, reacted at 94°C for 12h, TLC (petroleum ether-ethyl acetate 1:1) detected that the reaction was almost complete, adjusted the pH to 10 with 50% NaOH solution under cooling, dichloro Extract with methane (3×30mL), combine the organic phases, wash over anhydrous Na 2 SO 4 After drying, it was concentrated under reduced pressure to obtain 13.2 g of white crystals of ligustrazine mononitrogen oxide, yield 78.8%, mp 82.4-84.1°C.

[0036] Ligustrazine mononitrogen oxide (13.2g, 86.8mmol) and acetic anhydride (31.2mL, 330.4mmol) were sequentially added into a 250mL three-necked flask, reacted at 130°C for 5h, and detected by TLC...

Embodiment 2

[0051] Synthesis of (E)-2-ethyl(3-(3-(3,5,6-trimethylpyrazin-2-yl)acryloyl)phenoxy)ethyl ester (YA2)

[0052]

[0053] Reaction steps: the synthesis of 3,5,6-trimethylpyrazine-2-carbaldehyde was synthesized according to the method 1.1 and 1.2 in Example 1, and the operation was carried out according to the method 1.3 and 1.4 in Example 1 to obtain YA2 light yellow crystal, m.p.116.1 -116.9°C. 1 H NMR (300MHz, CDCl 3 )δ:8.19(d,J=14.7Hz,1H,=CH),8.00(d,J=14.7Hz,1H,=CH),7.77(d,J=7.5Hz,1H,PhH),7.62(s ,1H,PhH),7.45(t,J=7.8Hz,1H,PhH),7.18(dd,J=2.4Hz,8.1Hz,1H,PhH),4.72(s,2H,OCH 2 CO), 4.30 (q, J=7.2Hz, 2H, OCH 2 CH 3 ),2.66(s,3H,CH 3 ),2.57(s,3H,CH 3 ),2.55(s,3H,CH 3 ), 1.32(t, J=7.2Hz, 3H, OCH 2 CH 3 ); 13 C NMR (CDCl 3 ,75MHz)δ:189.5,168.5,158.1,152.8,149.9,149.6,142.9,139.3,138.5,129.8,126.1,122.3,120.0,113.9,65.4,61.5,22.1,21.8,20.8,14.2cm; IR(KBr, -1 )υ: 3067.9, 2981.5, 2914.2, 1742.1, 1658.7, 1585.7, 1482.6, 1450.5, 1437.5, 1398.4, 1211.7, 1186.2, 1085.2, 966.9, 8...

Embodiment 3

[0055] Synthesis of (E)-ethyl-2-methyl-2-(4-(3-(3,5,6-trimethylpyrazin-2-yl)acryloyl)phenoxy)propionate ( YA3)

[0056]

[0057] Reaction steps: the synthesis of 3,5,6-trimethylpyrazine-2-carbaldehyde is synthesized according to the method 1.1 and 1.2 in Example 1, and is operated according to the method 1.3 and 1.4 in Example 1 to obtain (E)-ethyl- 2-Methyl-2-(4-(3-(3,5,6-trimethylpyrazin-2-yl)acryloyl)phenoxy)propionate Yellow crystals, m.p.122.8-123.3°C. 1 H NMR (300MHz, CDCl 3 )δ: 8.13 (d, J = 14.7Hz, 1H, = CH), 8.00 (d, J = 8.7Hz, 2H, PhH), 7.91 (d, J = 14.7Hz, 1H, = CH), 6.83 (d ,J=8.7Hz,2H,PhH),4.16(q,J=7.2Hz,2H,OCH 2 CH 3 ),2.58(s,3H,CH 3 ),2.48(s,3H,CH 3 ),2.47(s,3H,CH 3 ),1.60(s,6H,2×CH 3 ), 1.15(t, J=7.2Hz, 3H, OCH 2 CH 3 ); 13 C NMR (CDCl 3 ,75MHz)δ:188.4,173.7,159.9,152.6,149.8,149.6,143.2,137.6,131.4,130.6,126.1,117.4,79.3,61.7,25.4,22.0,21.8,20.8,14.0; IR(KBr,cm -1 )υ: 3045.6, 2997.5, 2949.5, 1731.8, 1656.5, 1605.6, 1588.6, 1508.2, 1326.9, 1277.0...

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Abstract

The invention relates to the field of medical chemistry, in particular to a compound (I) containing ligustrazine chalcone aryloxy acids and a preparing method of the compound. It is proved through pharmacodynamic tests that the compound has the medical application of treating hyperlipidemia and antherosclerosis. The formula is shown in the specification.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a ligustrazine-based chalcone aryloxyalkanoic acid compound, a preparation method thereof and a medical application for treating hyperlipidemia and atherosclerosis. Background technique [0002] Hyperlipidemia is an increase in blood lipid and lipoprotein levels caused by abnormal lipid metabolism in the human body, including high levels of total cholesterol (TC), triglyceride (TG), low-density lipoprotein cholesterol (LDL-C) and Low levels of high-density lipoprotein cholesterol (HDL-C) are a major risk factor for diseases such as nonalcoholic fatty liver disease, atherosclerotic heart disease, and diabetes [see Ross R. The Pathogenesis of atherosclerosis: a perspective for the 1990s [J]. Nature, 1993, 362:801]. With the continuous improvement of people's living standards, the incidence of hyperlipidemia in my country continues to rise and presents a younger trend [see Zhao W...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/12A61K31/4965A61P7/02A61P3/06A61P9/10
CPCC07D241/12
Inventor 李家明何广卫储昭兴黄伟军张艳春谢迪左健刘会财
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE