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Glycyrrhetinic acid-piperazine compounds containing isopropanolamine substructure as well as preparation method and application thereof

A technology of propanolamine and glycyrrhetinic acid, applied in botany equipment and methods, steroids, applications, etc., can solve problems such as complex structure, difficult synthesis, easy volatility, and instability to light

Active Publication Date: 2020-01-21
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Natural products not only have a wide variety, diverse biological activities, and unique effects, but more importantly, they are easy to degrade or have good compatibility with the environment, so they have been widely used by people for thousands of years; however, due to the complex structure of most natural product compounds, it is difficult to synthesize. Most are unstable to light or extremely volatile, and usually cannot be directly used as pesticides

Method used

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  • Glycyrrhetinic acid-piperazine compounds containing isopropanolamine substructure as well as preparation method and application thereof
  • Glycyrrhetinic acid-piperazine compounds containing isopropanolamine substructure as well as preparation method and application thereof
  • Glycyrrhetinic acid-piperazine compounds containing isopropanolamine substructure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of intermediate 4-(oxyethylene-2-ylmethyl)-1-(18β-glycyrrhetinic acid group)-piperazine

[0060] Add 18β-glycyrrhetinic acid-30-piperazine (2.6mmol) into 20mL DMF solution dissolved with triethylamine (3.1mmol) and epibromohydrin (2.9mmol), react at room temperature for 12h, stop the reaction, extract with ethyl acetate , washed with saturated ammonium chloride, dried, precipitated, and column chromatographed to obtain a white solid with a yield of 66.4%. Its NMR data are: 1 H NMR (400MHz, CDCl 3 ) δ5.69 (s, 1H, 12-CH=C), 3.71-3.56 (m, 4H, 1'-NCH 2 ), 3.21 (dd, J=10.8, 5.3Hz, 1H, 3- CH OH), 3.13-3.04(m, 1H, 4'-OCH), 2.84-2.72(m, 3H, 1a-H+3'-N CH 2 CH), 2.66-2.40 (m, 5H, 2'-NCH 2 +5′a-CH 2 O), 2.35-2.17(m, 2H, 18-H+5'b-CH 2 O), 2.32(s, 1H, 9-H), 2.12-2.00(m, 2H, 16a-H+19a-H), 1.96(dd, J=13.6, 3.3Hz, 1H, 21a-H), 1.82 (td, J=13.5, 4.2Hz, 1H, 15a-H), 1.68-1.55(m, 5H, 6a-H+2-H+7a-H+21b-H), 1.51-1.34(m, 5H, 6b-H+7b-H+19b-H+22-H), 1.35(s, 3H, ...

Embodiment 2

[0061] Example 2: 1-(1-methylpiperazinyl)-3-(18β-glycyrrhetinic acid-30-piperazinyl)-2-hydroxypropanol

[0062] Add 4-(oxyethylene-2-ylmethyl)-1-(18β-glycyrrhetinyl)-piperazine (0.3mmol) into a solution of potassium carbonate (0.3mmol) and N-methylpiperazine (0.3 mmol) in 5 mL of isopropanol solution, reacted at 60°C for 24 h, then stopped the reaction, extracted with 30 mL of dichloromethane, washed with water, dried, precipitated, and column chromatographed to obtain a white solid with a yield of 74.9%.

[0063] The structure, H NMR spectrum and C NMR spectrum data of the synthesized 18β-glycyrrhetinic acid-30-piperazine compound containing isopropanolamine substructure are shown in Table 1, and the physicochemical properties are shown in Table 2.

[0064] Table 1 H NMR and C NMR data of the compounds

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079...

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Abstract

The invention relates to glycyrrhetinic acid-piperazine compounds containing an isopropanolamine substructure as well as a preparation method and application thereof. The compounds have structures asshown in a general formula (I) shown in the specification. On the basis of an 18beta-glycyrrhetinic acid compound, a nitrogen-containing fragment is introduced, and a series of 18beta-glycyrrhetinic acid-30-piperazine compounds containing isopropanolamine substructures are synthesized. The compounds have a good inhibition effect on plant pathogenic bacteria such as Xanthomonas oryzae pv.oryzae,Xooand Xanthomonas axonopodis pv.citri,Xac.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 18β-glycyrrhetinic acid-30-piperazine compound containing an isopropanolamine substructure and a preparation method and application thereof. Background technique [0002] Bacterial diseases not only seriously affect the yield of crops, but also threaten human health. For example, rice bacterial blight, citrus canker, kiwi fruit canker, and tobacco bacterial wilt cause huge economic losses to farmers every year. Long-term use of traditional fungicides, such as thiabylcopper, eucumazole, and Zhongshengmycin, not only increases the resistance of plant pathogens, but also has harmful effects on the environment and plant safety. Therefore, there is an urgent need to develop new pesticides with high activity and high selectivity. [0003] Natural products are important resources for the creation of new pesticides. Natural products not only have a wide variety, diverse ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A01N43/60A01N43/84A01P1/00A01P3/00
CPCC07J63/008A01N43/60A01N43/84
Inventor 杨松向猛王明伟曾丹姬瑾宋应莲
Owner GUIZHOU UNIV
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