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Glycyrrhetinic acid-hydrogen sulfide donor reagent derivative and its synthesis method and application

A hydrogen sulfide donor, glycyrrhetic acid technology, applied in the field of medicine, can solve problems such as no synthesis method and application

Inactive Publication Date: 2018-11-23
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, there are no relevant reports on the derivatives of glycyrrhetinic acid and hydrogen sulfide donor reagents connected through alkane chains and their synthesis methods and applications.

Method used

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  • Glycyrrhetinic acid-hydrogen sulfide donor reagent derivative and its synthesis method and application
  • Glycyrrhetinic acid-hydrogen sulfide donor reagent derivative and its synthesis method and application
  • Glycyrrhetinic acid-hydrogen sulfide donor reagent derivative and its synthesis method and application

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Experimental program
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Embodiment 1

[0041] Embodiment 1: the synthesis of compound 1a

[0042] Dissolve glycyrrhetinic acid (500mg, 1.06mmol) in anhydrous DMF (5mL), add 1,6-dibromoethane (2.43mL, 5.3mmol), K 2 CO 3 (146.28mg, 1.06mmol), reacted at 30°C for 24h. The solvent was evaporated under reduced pressure, and the residue was dispersed in ethyl acetate (50 mL), washed successively with HCl (1N), water, and saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and separated by column chromatography (V PE :V EA =2:1), to obtain compound 1a (457mg, 75%, white solid).

[0043] Yield: 457mg, 75%, white solid; R f =0.461 (Petroluem ether:EtOAc=2:1).M.p 190-192°C. 1 H NMR (500MHz, CDCl 3)δ (ppm): 5.69 (s, 1H, 12-H), 4.41 (dd, J = 28.0, 5.9Hz, 2H, OCH 2 ), 3.53(t, J=5.7Hz, 2H, OCH 2 ),3.21(dd,J=11.0,5.2Hz,1H,3-H),2.83-2.71(m,1H,18-H),2.32(s,1H),2.21-0.63(m,20H),1.35 , 1.17, 1.12, 1.11, 0.99, 0.80 and 0.79 (7s, each 3H, 7×CH 3 ). 13 C NMR (1...

Embodiment 2

[0045] Embodiment 2: the synthesis of compound 1b

[0046] Dissolve glycyrrhetinic acid (500mg, 1.06mmol) in anhydrous DMF (5mL), add 1,8-dibromobutane (2.94mL, 5.3mmol), K 2 CO 3 (146.28mg, 1.06mmol), reacted at 30°C for 24h. The solvent was evaporated under reduced pressure, and the residue was dispersed in ethyl acetate (50 mL), washed successively with HCl (1N), water, and saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and separated by column chromatography (V PE :V EA =2:1), to obtain compound 1b (532mg, 83%, white solid).

[0047] Yield: 532mg, 83%, white solid; R f =0.515 (Petroluem ether:EtOAc=2:1).M.p 82-84°C. 1 H NMR (500MHz, CDCl 3 )δ (ppm): 5.61 (s, 1H, 12-H), 4.12 (t, J = 6.3Hz, 2H, OCH 2 ), 3.43(t, J=6.5Hz, 2H, OCH 2 ), 3.21(dd, J=11.1, 5.1Hz, 1H, 3-H), 2.77(d, J=13.5Hz, 1H, 18-H), 2.32(s, 1H), 2.13-0.61(m, 24H ), 1.35, 1.14, 1.11, 1.10 and 0.98 (5s, each 3H, 5×CH 3 ),0.79(s,6H,2×CH ...

Embodiment 3

[0049] Embodiment 3: the synthesis of compound 1c

[0050] Dissolve glycyrrhetinic acid (1.0g, 2.12mmol) in anhydrous DMF (5mL), add 1,6-dibromohexane (1.62mL, 10.62mmol), K 2 CO 3 (293.0mg, 2.12mmol), reacted at 30°C for 24h. The solvent was evaporated under reduced pressure, the residue was dispersed in ethyl acetate (50ml), washed successively with HCl (1N), water, and saturated brine, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and separated by column chromatography (V PE :V EA =5:2), to obtain compound 1c (929mg, 69%, white solid).

[0051] Yield: 929mg, 69%, white solid; R f =0.452 (Petroluem ether:EtOAc=5:2).M.p 102-104°C. 1 H NMR (500MHz, CDCl 3 )δ (ppm): 5.61 (s, 1H, 12-H), 4.08 (m, 2H, OCH 2 ),3.39(m,2H,CH 2 -Br), 3.20(dd, J=11.1, 5.2Hz, 1H, 3-H), 2.76(d, J=13.5Hz, 1H, 18-H), 2.32(s, 1H, 10-H), 2.09 -0.69(m,35H),1.35,1.13,1.11,1.10and 0.98(5s,each 3H,5×CH 3 ),0.79(s,6H,2×CH 3 ). 13 C NMR (125MHz, CD...

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Abstract

The invention discloses a glycyrrhetinic acid-hydrogen sulfide donor reagent derivative, and a synthetic method and an application thereof. The synthetic method of the derivative comprises the following steps: carrying out a reaction on glycyrrhetinic acid, alpha,omega-dibromoalkane and an alkali in an aprotic polar solvent to obtain a compound 1; and carrying out a reaction on the compound 1, a hydrogen sulfide donor and the alkali in the aprotic polar solvent to obtain a crude target product, wherein the reactions are carried out under heating or non-heating conditions. Most compounds in the synthesized derivative have certain inhibition activity to a chronic marrow leukemia cell K562, and are hopeful to be used in the preparation of corresponding antitumor medicines and chronic marrow leukemia cell treatment medicines. The synthesized derivative has a structure represented by general formula (I) shown in the description; and in the general formula (I), n is 2-8, and R is one of three formulas shown in the description.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a glycyrrhetinic acid-hydrogen sulfide donor reagent derivative and its synthesis method and application. Background technique [0002] Hydrogen sulfide is a new biologically active gas molecule following CO and NO. It is an important role in supporting life. It has an irreplaceable physiological regulatory role in life activities, controls a variety of intracellular signal transduction processes and exerts positive regulation effect. At present, the potential therapeutic application of hydrogen sulfide mainly focuses on the nervous and cardiovascular systems, such as the treatment of hypertension, the treatment of cardiac ischemic diseases, the treatment of atherosclerosis, and the combination with non-steroidal anti-inflammatory drugs to reduce the Metabolism, prevention of hypoxic damage, etc. [0003] Hydrogen sulfide donors can be hydrolyzed and spontaneously emit H under...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P35/02
CPCC07J63/008
Inventor 程克光黄家艳张琚政莫伟彬邓胜平
Owner GUANGXI NORMAL UNIV
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