Ursolic acid-hydrogen sulfide donor reagent derivative and its synthesis method

A technology of hydrogen sulfide donor and synthesis method, applied in the field of medicine

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] There is no relevant report on derivatives and synthetic methods of ursolic acid and hydrogen sulfide donor reagents connected through alkane chains

Method used

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0042] Dissolve ursolic acid (1.0g, 2.19mmol) in anhydrous DMF (5mL), add 1,6-dibromohexane (2.67mL, 10.95mmol), K 2 CO 3 (302.78mg, 2.19mmol), 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 =3:1), to obtain compound 1a (1.207g, 89%, white solid).

[0043] Yield: 1.207g, 89%, white solid; R f =0.629 (Petroluem ether:EtOAc=3:1).M.p 102-104°C. 1 H NMR (500MHz, CDCl 3 )δ(ppm):5.22(s,1H,12-H),3.98(m,2H,OCH 2 ),3.40(m,2H,CH 2 -Br), 3.20(dd, J=11.0, 4.9Hz, 1H, 3-H), 2.20(s, 1H, 18-H), 2.02-072(m, 35H), 1.07, 0.98, 0.94, 0.91, 0.85,0.77 and 0.74(7s,each 3H,7×CH 3 ). 13 C NMR (125MHz, CDCl 3 )δ (ppm): 177.7, 138.3, 125.6, 79.2,...

Embodiment 2

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

[0046] Dissolve ursolic acid (1.0g, 2.19mmol) in anhydrous DMF (5mL), add 1,8-dibromooctane (1.84mL, 10.95mmol), K 2 CO 3 (302.78mg, 2.19mmol), 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 =4:1), to obtain compound 1b (1.162g, 82%, white solid).

[0047] Yield: 1.162g, 82%, white solid; R f =0.500(Petroluem ether:EtOAc=4:1).M.p 90-92°C. 1 H NMR (500MHz, CDCl 3 )δ(ppm):5.22(s,1H,12-H),3.97(m,2H,OCH 2 ),3.39(m,2H,CH 2 -Br), 3.20(dd, J=10.9, 4.7Hz, 1H, 3-H), 2.21(d, J=11.4Hz, 1H, 18-H), 2.02-0.69(m, 35H), 1.07, 0.98 ,0.93,0.91,0.85,0.77 and 0.74(7s,each 3H,7×CH 3 ). 13 C NMR (125MHz, CDCl 3 )δ (ppm): 177.7, 138.3125.6, 7...

Embodiment 3

[0049] Embodiment 3: the synthesis of compound 2a

[0050] Compound 1a (500mg, 0.81mmol) was dissolved in DMF (5mL), ADT-OH (182.60mg, 0.81mmol), K 2 CO 3 (335.83mg, 2.43mmol), KI (13.28mg, 0.08mmol), react at 65°C for 24h. The solvent was evaporated under reduced pressure, the residue was dispersed in ethyl acetate (50 mL), washed with HCl (1N), water, saturated brine successively, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated under reduced pressure, and separated by column chromatography (V PE :V EA =3:1), to obtain compound 2a (226mg, 37%, orange solid).

[0051] Yield: 226mg, 37%, orange solid; R f =0.579 (Petroluem ether:EtOAc=3:1).M.p 83-85°C. 1 H NMR (400MHz, CDCl 3 )δ(ppm): 7.60(d, J=8.9Hz, 2H, Ar-H), 7.39(s, 1H), 6.96(d, J=8.9Hz, 2H, Ar-H), 5.23(s, 1H ,12-H),4.02(m,4H,2×OCH 2 ), 3.21(dd, J=11.1, 4.4Hz, 1H, 3-H), 2.22(d, J=11.3Hz, 1H, 18-H), 2.12-0.65(m, 31H), 1.08, 0.98, 0.94 ,0.90and 0.85(5s,each 3H,5×CH 3 ),0.76(d,6H,2×CH 3 ...

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Abstract

The invention discloses an ursolic acid-hydrogen sulfide donor reagent derivative and a synthetic method thereof. The synthetic method of the derivative comprises the steps: taking ursolic acid, alpha,omega-dibromoalkane and an alkali, and carrying out a reaction in an aprotic polar solvent, to obtain a compound 1; taking the compound 1, a hydrogen sulfide donor reagent and an alkali, and carrying out a reaction in the aprotic polar solvent, to obtain a target crude product, wherein the reactions are carried out under the condition with or without heating. The synthesized derivative has the structure represented by the following general formula (I), wherein n is 2-8, and R is a group described in the specification, a group described in the specification or a group described in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an ursolic acid-hydrogen sulfide donor reagent derivative and a synthesis method thereof. 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 physiological c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61P35/00A61P35/02
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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