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Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs

A technology of glycyrrhetinic acid and anti-inflammatory drugs, applied in the direction of anti-inflammatory agents, drug combinations, antipyretics, etc., can solve the problem of no anti-inflammatory activity, etc., to avoid gastrointestinal damage and/or cardiovascular adverse events or other toxic side effects, reducing cardiovascular events, high anti-inflammatory activity

Inactive Publication Date: 2012-07-18
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there is no reference to H in the prior art 2 Report on Anti-inflammatory Activity of S Donor Glycyrrhetinic Acid Derivatives and Their Pharmaceutically Acceptable Salts

Method used

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  • Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs
  • Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs
  • Application of glycyrrhetinic acid derivatives in preparation process of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 5-[4-(2-bromoethoxy)phenyl]-3H-1,2-dithiol-3-thione (5a)

[0037] ADT-OH (0.325g, 1.4mmol), 1,2-dibromoethane (0.50mL, 5.8mmol), anhydrous K 2 C0 3 (0.396g, 2.8mmol), dissolved in 10mL dry DMF, reacted at 120°C for 2h. After cooling, add 20mL ethyl acetate to dilute, wash with water (3×20mL), anhydrous Na 2 SO 4 dry. Filter, evaporate to dryness under reduced pressure, and recrystallize from acetone-water to obtain 0.388 g of dark brown product with a yield of 81.5%, mp: 126.0-127.0°C. 1 HNMR(400MHz, CDCl 3 ), δ (ppm): 7.59 (d, 2H, J = 8.9 Hz, ArH), 7.36 (s, 1H, = CH), 6.96 (d, 2H, J = 8.9 Hz, ArH), 4.33 (t, 2H , J=6.1Hz, CH 2 ), 3.65(t, 2H, J=6.1Hz, CH 2 ); 13 CNMR(400MHz, CDCl 3 ), δ (ppm): 212.554, 170.180, 158.775, 132.260, 126.120, 122.226, 113.014, 65.455, 26.026.

[0038] The above identification data proves that the compound obtained is 5-[4-(2-bromoethoxy)phenyl]-3H-1,2-dithiol-3-thione (5a), and its structural formula is:

[0039] Compound I 1 Prepa...

Embodiment 2

[0044] Preparation of 5-[4-(3-bromopropoxy)phenyl]-3H-1,2-dithiol-3-thione (5b)

[0045] Using 1,3-dibromopropane as the raw material, it was prepared by referring to the method of 5a, the yield was 83.2%, mp: 79.0-80.0°C. 1 HNMR(400MHz, CDCl 3 ), δ (ppm): 7.62 (d, 2H, J = 8.8 Hz, ArH), 7.40 (s, 1H, = CH), 7.00 (d, 2H, J = 8.7 Hz, ArH), 4.19 (t, 2H , J=5.8Hz, CH 2 ), 3.62(t, 2H, J=6.3Hz, CH 2 ), 2.36(p, 2H, J=6.0Hz, CH 2 ); 13 CNMR(400MHz, CDCl 3 ), δ (ppm): 212.460, 170.437, 159.454, 132.073, 126.065, 121.751, 112.886, 63.118, 29.453, 27.178.

[0046] The above identification data proves that the obtained compound is 5-[4-(3-bromopropoxy)phenyl]-3H-1,2-dithio-3-thione (5b), and its structural formula is:

[0047] Compound I 2 Preparation

[0048] Using GA and 5b as raw materials, refer to I 1 Prepared by synthetic method, red solid, yield 86.6%, mp: 79.1-80.7°C. 1 HNMR(400MHz, CDCl 3 ), δ (ppm): 7.54 (d, 2H, J = 8.8 Hz, ArH), 7.31 (s, 1H, = CH), 6.91 (d, 2H, J = 8.8 Hz, ArH), 5.54 (...

Embodiment 3

[0052] Preparation of 5-[4-(4-bromobutoxy)phenyl]-3H-1,2-dithiol-3-thione (5c)

[0053] Using 1,4-dibromobutane as the raw material, it is prepared by referring to the method of 5a, the yield is 79.4%, mp: 70.0-71.0°C. 1 HNMR(400MHz, CDCl 3 ), δ (ppm): 7.60 (d, 2H, J = 8.7 Hz, ArH), 7.38 (s, 1H, = CH), 6.96 (d, 2H, J = 8.7 Hz, ArH), 4.07 (t, 2H , J=5.9Hz, CH 2 ), 3.50(t, 2H, J=6.4Hz, CH 2 ), 2.08(m, 2H, CH 2 ), 1.99(m, 2H, CH 2 ); 13 CNMR(400MHz, CDCl 3 ), δ (ppm): 212.439, 170.554, 159.670, 132.006, 126.057, 121.553, 112.834, 64.759, 30.795, 26.729, 25.133.

[0054] The above identification data proves that the compound obtained is 5-[4-(4-bromobutoxy)phenyl]-3H-1,2-dithiol-3-thione (5c), and its structural formula is:

[0055] Compound I 3 Preparation

[0056] Using GA and 5c as raw materials, refer to I 1 Prepared by synthetic method, red solid, yield 89.2%, mp: 138.2-139.2°C. 1 HNMR(400MHz, CDCl 3 ), δ (ppm): 7.60 (d, 2H, J = 8.8 Hz,), 7.39 (s, 1H, = CH), 6.98 (d, 2H, J = 8.8 Hz,...

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Abstract

The invention discloses the application of glycyrrhetinic acid derivatives in the preparation process of anti-inflammatory drugs, in particular to the glycyrrhetinic acid derivatives as well as pharmaceutically acceptable salt thereof, drug compositions containing the derivatives and anti-inflammatory action of the drug compositions, wherein, the glycyrrhetinic acid derivatives can release gaseous signal molecule hydrogen sulfide. The invention discloses and provides the glycyrrhetinic acid derivatives that can release gaseous signal molecule H2S, wherein, glycyrrhetinic acid and gaseous signal molecule hydrogen sulfide release groups are coupled through ester bonds or amido bonds so as to obtain the glycyrrhetinic acid derivatives. Pharmacology experimental results show that the glycyrrhetinic acid derivatives achieve remarkable anti-inflammatory action and have no significant gastrointestinal tract injury, and show that the glycyrrhetinic acid derivatives can be used for preparing the drugs for treating various inflammations and related diseases thereof.

Description

Technical field [0001] The present invention relates to the field of medicine, in particular to a class of glycyrrhetinic acid derivatives that can release gaseous signal molecule hydrogen sulfide and their pharmaceutically acceptable salts, and pharmaceutical compositions containing these derivatives, which have anti-inflammatory effects, especially in Application for preparing anti-inflammatory diseases. Background technique [0002] The legume licorice is an important traditional Chinese medicine. Glycyrrhizic acid and its salt (namely glycyrrhizin) are the main active ingredients of glycyrrhizinate, which are hydrolyzed into glycyrrhetinic acid (GA) by gastric acid in the human body. Modern research shows that GA has various pharmacological activities such as anti-inflammatory, anti-oxidant, anti-ulcer, anti-viral, anti-arrhythmic, hypolipidemic, anti-tumor and anti-allergic effects. GA has obvious effects on inflammatory bowel disease, rheumatoid arthritis, gingivitis, per...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P29/00C07J63/00
Inventor 敖桂珍绪广林杨圣伟张英候丙波楚小晶
Owner SUZHOU UNIV
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