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Acetoxyl ursolic acid piperazine compound containing isopropanolamine substructure, and preparation method and application of acetoxyl ursolic acid piperazine compound

A technology of acetoxyursolic acid and propanolamine, which is applied in the field of 3β-acetoxyursolic acid-28-piperazine compounds and its preparation, can solve the problems of low inhibitory concentration and reduction

Active Publication Date: 2020-02-11
GUIZHOU UNIV
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  • Claims
  • Application Information

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Problems solved by technology

[0008] In 2015, Dwivedi et al [Dwivedi, G.R., Maurya, A., Yadav, D.K., Khan, F., Darokar, M.P., Srivastava, S.K. Drug resistance reversal potential of ursolic acid derivatives against nalidixic acid and multidrug resistant Escherichia coli[J]. Chem Boil Drug Des., 2015, 86, 272-283.] reported that 6 semi-synthetic ursolic acid derivatives were synthesized, and the biological activity test results showed that although all semi-synthetic ursolic acid derivatives themselves were sensitive to p-naphthyridine Ketoacid-sensitive and nalidixic acid-resistant E. coli strains had no significant biological activity, but when combined with nalidixic acid, they greatly reduced nalidixic acid compared to nalidixic acid. Minimum Inhibitory Concentrations (MIC) for Sensitive and Nalidixic Acid-Resistant E. coli Strains

Method used

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  • Acetoxyl ursolic acid piperazine compound containing isopropanolamine substructure, and preparation method and application of acetoxyl ursolic acid piperazine compound
  • Acetoxyl ursolic acid piperazine compound containing isopropanolamine substructure, and preparation method and application of acetoxyl ursolic acid piperazine compound
  • Acetoxyl ursolic acid piperazine compound containing isopropanolamine substructure, and preparation method and application of acetoxyl ursolic acid piperazine compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the preparation of intermediate 3β-acetoxy ursolic acid

[0056] Add ursolic acid (21.9mmol) to 20mL of anhydrous pyridine dissolved with DMAP (2.6mmol) and acetic anhydride (87.6mmol), stop the reaction after 12 hours at room temperature, remove the solvent, add 50mL of water, wash with dilute hydrochloric acid Adjust the pH to 2-3, and filter with suction to obtain a white solid with a yield of 94.4%. Its NMR data are: 1 H NMR (400MHz, CDCl 3 )δ5.22(t, J=3.2Hz, 1H, 12-CH=C), 4.55-4.43(m, 1H, 3- CH OOCCH 3 ), 2.17(d, J=11.2Hz, 1H, 18-H), 2.04(s, 3H, 2'-CH 3 COO), 2.01-1.80(m, 4H, 11-H+2-H), 1.76-1.58(m, 6H, 16-H+9-H+22-H+20-H), 1.56-1.42(m , 4H, 6a-H+1-H+19-H), 1.37-1.24(m, 5H, 6b-H+21-H+7-H), 1.10-1.02(m, 2H, 15-H), 1.06(s, 3H, 27-CH 3), 0.94 (d, J=8.2Hz, 3H, 30-CH 3 ), 0.93(s, 3H, 23-CH 3 ), 0.86(s, 3H, 25-CH 3 ), 0.85 (d, J=7.5Hz, 3H, 29-CH 3 ), 0.84(s, 3H, 26-CH 3 ), 0.81(s, 1H, 5-H), 0.76(s, 3H, 24-CH 3 ); 13 C NMR (101MHz, CDCl 3 )δ 1...

Embodiment 2

[0057] Embodiment 2: the preparation of intermediate 3β-acetoxy ursolic acid-28-acyl chloride

[0058] Slowly add oxalyl chloride (41.2mmol) dropwise into 30mL of dichloromethane solution dissolved with 3β-acetoxyursolic acid (20.6mmol), stop the reaction after reacting at room temperature for 4h, desolventize the system, and set aside;

Embodiment 3

[0059] Embodiment 3: the preparation of intermediate 3β-acetoxy ursolic acid-28-piperazine

[0060] Dissolve the 3β-acetoxyursolic acid-28-acyl chloride obtained above in 20mL of dichloromethane, and slowly add it dropwise to the solution containing anhydrous piperazine (61.8mmol) and triethylamine (41.2mmol) under ice-bath conditions. ) in 20mL of dichloromethane, reacted at 0°C for 8h, then stopped the reaction, extracted with 50mL of dichloromethane, washed with water, dried, precipitated, and column chromatographed to obtain a white solid with a yield of 86.6%. Its NMR data are: 1 H NMR (400MHz, CDCl 3 )δ5.21 (s, 1H, 12-CH=C), 4.48 (dd, J=8.9, 7.1Hz, 1H, 3- CH OOCCH 3 ), 3.57 (s, 4H, 1'-NCH 2 ), 2.82 (s, 4H, 2'-NCH 2 ), 2.12(d, J=13.2Hz, 1H, 18-H), 2.04(s, 3H, 4'-CH 3 COO), 1.91(d, J=7.2Hz, 2H, 11-H), 1.78-1.57(m, 8H, 2-H+16-H+9-H+22-H+20-H), 1.56- 1.42(m, 4H, 6a-H+1-H+19-H), 1.42-1.22(m, 5H, 6b-H+21-H+7-H), 1.11-1.00(m, 2H, 15- H), 1.06(s, 3H, 27-CH 3 ), 0.93 (d,...

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Abstract

The invention relates to an acetoxyl ursolic acid piperazine compound containing an isopropanolamine substructure, and a preparation method and application of the acetoxyl ursolic acid piperazine compound. The compound has a structure disclosed in a following general formula (I): an ursolic acid compound is taken as a basis, a nitrogen-containing fragment is introduced into the system to synthesize one series of 3[beta]-acetoxyl ursolic acid-28-piperazine compound containing the isopropanolamine substructure, and the compound has a good inhibition effect on plant pathogenic bacteria, includingxanthomonas oryzaepv. oryzae, xanthomonas axonopodis pv. Citri and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 3β-acetoxyursolic acid-28-piperazine compound containing an isopropanolamine substructure and a preparation method and application thereof. Background technique [0002] In recent years, plant bacteria and fungi have seriously affected the yield and quality of crops worldwide, causing huge economic losses to farmers. For example, rice bacterial blight (Xanthomonas oryzaepv.Oryzae) is a rod-shaped Gram-negative bacterium that can cause the leaves of rice to wither and turn white, and it brings at least 10-50% of rice-growing countries every year. production cuts. Additionally, Xanthomonas axonopodis pv. Citri causes citrus rot, affecting citrus yields globally. In the process of agricultural production, due to the long-term use of traditional medicaments, plant pathogenic bacteria have developed certain resistance to them. Therefore, it is of great significance to...

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 杨松王培义向猛王明伟曾丹姬瑾宋应莲
Owner GUIZHOU UNIV
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