Piperazine-framework-containing glycyrrhetinic acid derivatives, and preparation method and application thereof

A technique for glycyrrhetinic acid and derivatives, applied in the field of glycyrrhetinic acid derivatives

Inactive Publication Date: 2016-06-15
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Glycyrrhetinic acid has been shown to have anti-inflammatory, anti-viral

Method used

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  • Piperazine-framework-containing glycyrrhetinic acid derivatives, and preparation method and application thereof
  • Piperazine-framework-containing glycyrrhetinic acid derivatives, and preparation method and application thereof
  • Piperazine-framework-containing glycyrrhetinic acid derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 3βhydroxy-30-(4-phenyl-1-piperazinyl)-olean-12-ene-11,30-dione (3a)

[0021]

[0022] At room temperature, 20 mL of dichloromethane solution was added to the reaction vessel, followed by adding 1.2 mmol each of DCC and HOBT, stirring at room temperature for 30 min, then adding glycyrrhetinic acid (1 mmol) and stirring at room temperature for 20 min. Then phenylpiperazine (1.2mmol) and triethylamine (3mmol) were stirred at room temperature for 24h, and the reaction was tracked by TLC. After sufficient reaction, compound 3a was obtained. Yield: 83%.M.p.282-284℃. 1 HNMR (400MHz, DMSO-d 6 ): δ (ppm) 7.20-7.27 (m, 2H, Ar-7', 9'), 6.94 (d, J=7.92Hz, 2H, Ar-6', 10'), 6.81 (t, J=7.24 Hz, 1H, Ar-8'), 5.48(s, 1H, CH-12), 4.32(d, J=5.16Hz, 1H, -OH), 3.70(s, 4H, CH 2 -1', CH 2 -4'), 3.10(t, J=4.60Hz, 4H, CH 2 -2', CH 2 -3'), 2.98-3.05(m, 1H, CH-3), 2.57(d, J=13.32Hz, 1H, CH-18), 2.33(s, 1H, CH-9), 2.26-1.36(m , 16H, CH 2 -2,CH 2 -6,CH 2 -7,CH ...

Embodiment 2

[0023] Example 2: Preparation of 3βhydroxy-30-(4-(2,4-dimethylphenyl)-1-piperazinyl)-olean-12-ene-11,30-dione (3b)

[0024]

[0025] The preparation method refers to Example 1. Yield: 79%. M.p.175-177℃. 1 HNMR (400MHz, DMSO-d 6 ): δ (ppm) 6.88-7.00 (m, 3H, Ar-6'7', 9'), 5.52 (s, 1H, CH-12), 4.32 (d, J=5.16Hz, 1H, -OH) , 3.68(s, 4H, CH 2 -1', CH 2 -4'), 2.99-3.05(m, 1H, CH-3), 2.75(s, 4H, CH 2 -2', CH 2 -3'), 2.57(d, J=13.36Hz, 1H, CH-18), 2.33(s, 1H, CH-9), 2.22(d, J=7.04Hz, 6H, Me-8', Me- 10'), 2.17-1.37(m, 16H, CH 2 -2,CH 2 -6,CH 2 -7,CH 2 -15,CH 2 -16,CH 2 -19, CH 2 -21,CH 2 -22), 1.35(s, 3H, Me-27), 1.19(s, 3H, Me-29), 1.03(d, J=1.64Hz, 6H, Me-25, Me-26), 0.97(d, J=14.32Hz, 2H, CH 2 -1), 0.91(s, 3H, Me-23), 0.75(s, 3H, Me-24), 0.71(s, 1H, CH-5), 0.69(s, 3H, Me-28).

Embodiment 3

[0026] Example 3: Preparation of 3βhydroxy-30-(4-(4-nitrophenyl)-1-piperazinyl)-olean-12-ene-11,30-dione (3c)

[0027]

[0028] The preparation method refers to Example 1. Yield: 74%. M.p.252-254℃. 1 HNMR (400MHz, DMSO-d 6 ): δ (ppm) 8.09 (d, J=9.44Hz, 2H, Ar-7', 9'), 7.00 (d, J=9.52Hz, 2H, Ar-6', 10'), 5.50(s, 1H, CH-12), 4.32 (d, J=5.16Hz, 1H, -OH), 3.72 (s, 4H, CH 2 -1', CH 2 -4'), 3.48(d, J=4.56Hz, 4H, CH 2 -2', CH 2 -3'), 2.99-3.05(m, 1H, CH-3), 2.57(d, J=13.36Hz, 1H, CH-18), 2.33(s, 1H, CH-9), 2.24-1.36(m , 16H, CH 2 -2,CH 2 -6,CH 2 -7,CH 2 -15,CH 2 -16,CH 2 -19, CH 2 -21,CH 2 -22), 1.35(s, 3H, Me-27), 1.19(s, 3H, Me-29), 1.03(s, 6H, Me-25, Me-26), 0.97(d, J=13.64Hz, 2H, CH 2 -1), 0.91(s, 3H, Me-23), 0.74(s, 3H, Me-24), 0.71(s, 1H, CH-5), 0.69(s, 3H, Me-28).

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Abstract

The invention discloses piperazine-framework-containing glycyrrhetinic acid derivatives, and a preparation method and application thereof. The structure of the synthesized glycyrrhetinic acid derivatives is disclosed in the specification. The glycyrrhetinic acid derivatives have obvious inhibiting actions on human liver cancer cells (HepG2), human mammary cancer cells (MCF-1), cervical cancer cell lines (Hela cells) and human lung adenocarcinoma cells (A549). Therefore, the piperazine-framework-containing glycyrrhetinic acid derivatives can be used for preparing antineoplastic drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a glycyrrhetinic acid derivative containing a piperazine skeleton, a preparation method and an application thereof. Background technique [0002] Various physiological and pathological processes in the human body involve neovascularization, which refers to the process of sprouting new blood vessels from pre-existing capillaries, which plays an important role in tumor growth and metastasis. The most important of these is vascular endothelial growth factor (VEGF), which plays an important role in tumor angiogenesis, vascular permeability, endothelial cell activation, proliferation and migration. The VEGFR family includes VEGFR1, VEGFR2 and VEGFR3. VEGFR2, which plays a prominent role in the regulation of endothelial cell responses driven by VEGF, is a tyrosine kinase receptor involved in blood vessels and mediates endothelial cell proliferation, differentiation, and ...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/58A61P35/00
CPCC07J63/00
Inventor 朱海亮晏天龙齐海霞王泽峰王忠长
Owner NANJING UNIV
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