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Glycyrrhetinic acid derivative and application thereof as antitumor medicament

Technology of an anti-tumor drug, glycyrrhetinic acid, applied in the field of medicine

Inactive Publication Date: 2013-06-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there is no pair of H in the prior art 2 Any reports on S-donor glycyrrhetinic acid derivatives and their pharmaceutically acceptable salts, nor any reports on the biological activity of such compounds

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 5-[4-(2-bromoethoxy)phenyl]-3H-1,2-dithiole-3-thione ( 5a ) preparation

[0033] ADT-OH (0.325g, 1.4mmol), 1,2-dibromoethane (0.50mL, 5.8mmol), anhydrous K 2 CO 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, yield 81.5%, mp: 126.0~127.0°C. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 7.59(d, 2H, J =8.9Hz, ArH), 7.36(s, 1H, =CH), 6.96 (d, 2H, J =8.9Hz, ArH), 4.33(t, 2H, J =6.1Hz,CH 2 ), 3.65(t, 2H, J = 6.1 Hz, CH 2 ); 13 C NMR (400MHz, CDCl 3 ), δ(ppm): 212.554, 170.180, 158.775, 132.260, 126.120, 122.226, 113.014, 65.455, 26.026.

[0034] Above-mentioned identification data proves that gained compound is 5-[4-(2-bromoethoxy) phenyl]-3H-1,2-dithiole-3-thione ( 5a ), its structural formula is: .

[0035] Comp...

Embodiment 2

[0039] 5-[4-(3-bromopropoxy)phenyl]-3H-1,2-dithiole-3-thione ( 5b ) preparation

[0040] With 1,3-dibromopropane as raw material, refer to 5a prepared by the method, yield 83.2%, mp: 79.0~80.0℃. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 7.62(d, 2H, J = 8.8Hz, ArH), 7.40(s, 1H, =CH), 7.00(d, 2H, J = 8.7Hz, ArH), 4.19(t, 2H, J = 5.8 Hz, CH 2 ), 3.62(t, 2H, J = 6.3Hz, CH 2 ), 2.36(p, 2H, J =6.0 Hz, CH 2 ); 13 C NMR (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. The above identification data prove that the obtained compound is 5-[4-(3-bromopropoxy)phenyl]-3H-1,2-dithio-3-thione ( 5b ), its structural formula is: .

[0041] Compound I 2 preparation of

[0042] Take GA and 5b as raw material, refer to Ⅰ 1 Prepared by the synthetic method of , red solid, yield 86.6%, mp: 79.1~80.7℃. 1 H NMR (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), 5.5...

Embodiment 3

[0045] 5-[4-(4-bromobutoxy)phenyl]-3H-1,2-dithiole-3-thione ( 5c ) preparation

[0046] With 1,4-dibromobutane as raw material, refer to 5a prepared by the method, yield 79.4%, mp: 70.0~71.0℃. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 7.60(d, 2H, J = 8.7Hz, ArH), 7.38(s, 1H, =CH), 6.96(d, 2H, J =8.7Hz, 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 C NMR (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. The above identification data prove that the compound obtained is 5-[4-(4-bromobutoxy)phenyl]-3H-1,2-dithiole-3-thione ( 5c ), its structural formula is: .

[0047] Compound I 3 preparation of

[0048] Take GA and 5c as raw material, refer to Ⅰ 1 Prepared by the synthetic method of , red solid, yield 89.2%, mp: 138.2~139.2℃. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 7.60 (d, 2H, J= 8.8Hz,), 7.39 (s, 1H, =CH), 6.98(d, 2H, J= 8.8 Hz, Ar...

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Abstract

The present invention relates to the field of medicine, in particular to a class of glycyrrhetinic acid derivatives capable of releasing gas signal molecule hydrogen sulfide and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing these derivatives and their anti-inflammatory agents. Tumor effects, especially in the preparation of drugs against tumor diseases. The glycyrrhetinic acid derivatives are composed of glycyrrhetinic acid and its derivatives and hydrogen sulfide donors coupled through ester bonds or amide bonds. The present invention discloses for the first time a glycyrrhetinic acid derivative that can release gas signal molecule H2S , obtained antitumor drugs with higher activity by modifying glycyrrhetinic acid.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to a class of glycyrrhetinic acid derivatives capable of releasing gas signal molecule hydrogen sulfide and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing these derivatives and their anti-inflammatory agents. Tumor effects, especially in the preparation of drugs against tumor diseases. Background technique [0002] Licorice belongs to leguminous plants, mainly distributed in western my country and other regions, and is one of the commonly used Chinese herbal medicines in my country. Glycyrrhizic acid and its aglycone glycyrrhetinic acid (glycyrrhetinic acid, GA for short) are the main pharmacological active substances of licorice. Modern studies have shown that GA has various pharmacological activities such as anti-inflammation, anti-ulcer, anti-virus, anti-arrhythmia, lowering blood fat, promoting insulin absorption, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00
Inventor 敖桂珍乔春华候丙波曹毅楚小晶
Owner SUZHOU UNIV