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Liquorice gadoleic acid derivative as well as preparation method and application thereof

A technology of glycyrrhizic acid and derivatives, which can be used in drug combinations, pharmaceutical formulations, steroids, etc., can solve problems such as tissue damage, and achieve inhibition of the production of inflammatory signaling molecule NO, strong inhibitory activity, and good inflammatory signaling molecule NO. the effect of

Active Publication Date: 2017-11-07
亿利耐雀生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inflammatory process itself can lead to tissue damage and lead to many diseases and even cancer (R. Medzhitov, Nature, 2008, 454, 428-435)

Method used

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  • Liquorice gadoleic acid derivative as well as preparation method and application thereof
  • Liquorice gadoleic acid derivative as well as preparation method and application thereof
  • Liquorice gadoleic acid derivative as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1～ Embodiment 16

[0044] The preparation of derivative 1~derivative 16 (synthetic route such as figure 1 shown)

[0045] Reference (Beseda I et al., Bioorg. Med. Chem., 2010, 18(1), 433-54), Synthesis of Glycyrrhizin.

[0046]Add 80% sodium hydride (6.0mmol) into anhydrous tetrahydrofuran (100mL), stir at 0°C to 5°C, under nitrogen protection, slowly add triethyl phosphoroacetate (6.0mmol) dropwise over 30 minutes, after the addition is complete , stirred for 1 hour under the same conditions; the obtained glycyrrhizin (5.0mmol) was dissolved in anhydrous tetrahydrofuran (30mL), and was added dropwise to the above mixed reaction solution in 30 minutes under ice-bath conditions, stirred at room temperature for 2 to 3 hours, TLC Monitoring, until the reaction of glycyrrhizin is complete, stop the reaction; filter the reaction solution, wash twice with ethyl acetate, combine the filtrate, extract, wash the organic phase twice with water, dry over anhydrous sodium sulfate, filter and concentrate un...

Embodiment 1

[0051] Derivative 1: white powder, yield 64%, m.p.254-257°C; 1H-NMR (300MHz, CDCl3), δ(ppm): 6.89 (d, 1H, J=16.2Hz, H-30), 5.79 (d,1H,J=16.2Hz,H-31),5.63(s,1H,H-12),4.52(dd,1H,J=11.4,5.0Hz,H-1),4.20(q,2H, J=7.1Hz, OCH2CH3), 2.80(dt, 1H, J=13.5, 3.3Hz, H-5), 2.36 (s, 1H, H-9), 2.05(s, 3H, OAc), 1.38(s, 3H,H-27),1.13(s,3H,H-25),1.12(s,3H,H-26),1.00(s,3H,H-23),1.01(s,3H,H-29) ,0.81(s,3H,H-24),0.80(s,3H,H-28).

Embodiment 2

[0053] Derivative 2: white powder, yield 91%; m.p.259-262°C; 1H-NMR (300MHz, CDCl3), δ (ppm): 7.00 (d, 1H, J=16.2Hz, H-30), 5.82 (d, 1H, J=16.2Hz, H-31), 5.66(s, 1H, H-12), 3.73(q, 2H, J=7.0Hz), 3.24(dd, 1H, J=9.8, 6.5Hz ,H-3),2.79(d,1H,J=13.5,H-18),2.36(s,1H,H-9),1.38(s,3H,H-27),2.34(s,1H,H -9),1.13(s,3H,H-25),1.12(s,3H,H-26),1.00(s,3H,H-23),1.01(s,3H,H-29),0.81( s,3H,H-24),0.80(s,3H,H-28); 13C-NMR(75MHz,CDCl3),δ(ppm):200.3(C-11), 170.43(C-13),169.5( C-32), 157.9 (C-30), 128.3 (C-12), 119.4 (C-31), 78.8 (C-3), 61.8 (C-9), 58.4 (C-22), 54.9 (C -5), 47.4(C-18), 45.4(C-8), 43.3(C-14), 42.8(C-20), 39.1(C-4), 39.1(C-1), 38.0(C- 10), 37.1(C-19), 36.7(C-21), 32.7(C-2), 32.2(C-7), 30.7(C-17), 28.4(C-28), 28.0(C-23 ), 26.4 (C-16), 26.3 (C-15), 23.5 (C-20), 18.6 (C-26), 18.4 (C-27), 17.4 (C-6), 16.3 (C-25) ,15.5(C-24).

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Abstract

The invention discloses a liquorice gadoleic acid derivative. A structure of the liquorice gadoleic acid derivative is shown as a general formula in an abstract figure; the invention further discloses a preparation method of the liquorice gadoleic acid derivative. The invention further discloses application of the liquorice gadoleic acid derivative serving as an anti-inflammatory drug; specifically, the liquorice gadoleic acid derivative can be applied to drugs or drug compositions for treating and preventing related diseases including acute lung injury, chronic obstructive pulmonary disease, sepsis and the like.

Description

technical field [0001] The invention relates to a glycyrrhizinic acid derivative, a preparation method thereof and an anti-inflammatory application, belonging to the technical field of proposal, preparation and application of new compounds. Background technique [0002] Inflammation is a fundamental defense mechanism of the immune system that protects against damage caused by harmful stimuli such as pathogens and poisons. However, the inflammatory process itself may lead to tissue damage and lead to many diseases and even cancer (R. Medzhitov, Nature, 2008, 454, 428-435). Inflammation is a complex defense response of living tissue with vascular system to injury factors (trauma, infection, ischemia, poisoning or autoimmune injury) (Hsu CC, Lien JC. et al., Biochemical Pharmacology, 2013, 85, 385-395), moderate The inflammatory response is an important process for the host to defend against harmful stimuli and initiate healing, but acute inflammation may lead to pathological ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P11/00A61P29/00A61P31/00
CPCC07J63/008
Inventor 汤文建杨永安陈世超李波陈锐
Owner 亿利耐雀生物科技有限公司
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