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
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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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