Andrographolide compounds and preparation method and application thereof
A compound and solvate technology, applied in the field of medicine, can solve the problems of poor selectivity of anti-inflammatory drugs, limited clinical application, obvious side effects, etc., and achieve the effects of good drug resistance, high purity of drugs, and strong anti-inflammatory activity
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Embodiment 1
[0056] Embodiment 1: the preparation of compound of the present invention
[0057] (1R,2R,4aS,5R)-1(hydroxymethyl)-1,4-dimethyl-6-methylene-5-(2-(naphthalene-1-oxyl)ethyl)decalin Preparation of -2-alcohol (compound 1 for short):
[0058] Andrographolide (15g, 42.8mmol) was placed in a 250mL round bottom flask, 150mL of anhydrous acetone was added, the reaction system was cloudy, then 2,2-dimethoxypropane (15.8mL, 0.13mol) and catalyst were added A certain amount of pyridinium p-toluenesulfonate (PPTS) was reacted at room temperature for 2 hours, and the reaction solution was clear at this time. After the reaction is over, distill off the acetone under reduced pressure, redissolve with dichloromethane (100mL), wash once with saturated sodium bicarbonate (100mL), once with water (100mL), once with saturated brine (100mL), and once with anhydrous sulfuric acid. Sodium dry. 16.2 g of white solid (IM-1) was obtained with a yield of 97%.
[0059] Dissolve IM-1 (14g, 35.8mmol) in...
Embodiment 2
[0065] (1R,2R,4aS,5R)-1(hydroxymethyl)-1,4-dimethyl-6-methylene-5-(2-(4-phenoxyphenoxy)ethyl)deca The preparation of hydronaphthalene-2-ol (abbreviation compound 2):
[0066] The specific operation and proportion refer to the preparation of Compound 1.
[0067] Get (1R,2R,4aS,5R)-1(hydroxymethyl)-1,4-dimethyl-6-methylene-5-(2-(4-phenoxyphenoxy)ethyl) Decalin-2-ol. 1 H-NMR (600MHz, CDCl 3 ):δ7.29(2H,t,J=7.8Hz,3″,5″-H),7.03(1H,t,J=7.2Hz,4″-H),6.94(4H,m,3′, 5′, 2″, 6″-H), 6.83 (2H, d, J=9.0Hz, 2′, 6′-H), 4.87 (1H, s, 13a-H), 4.59 (1H, s, 13b -H), 4.21(1H,d,J=11.4Hz,15a-H),4.02(1H,m,12a-H),3.80(1H,m,12b-H),3.51(1H,m,3- H), 3.34(1H,d,J=11.4Hz,15b-H),2.83(2H,s,7-H),1.26(3H,s,16-H),0.68(3H,s,14-H ). 13 C-NMR (150MHz, CDCl 3 ):δ158.5,155.3,149.9,147.3,129.5,129.5,122.3,120.7,120.7,117.5,117.5,115.4,115.4,107.2,80.6,67.5,64.1,55.2,52.5,482.8,32.8,362.0,37. 23.9, 23.8, 22.6, 15.1.
Embodiment 3
[0069] (1R,2R,4aS,5R)-5-(2-(4-(tert-butyl)phenoxy)ethyl)-1-(hydroxymethyl)-1,4-dimethyl-6-ylidene The preparation of methyl decalin-2-alcohol (abbreviation compound 3):
[0070] The specific operation and proportion refer to the preparation of Compound 1.
[0071] Get (1R,2R,4aS,5R)-5-(2-(4-(tert-butyl)phenoxy)ethyl)-1-(hydroxymethyl)-1,4-dimethyl-6- Methylenedecalin-2-ol. 1 H-NMR (600MHz, CDCl 3 ):δ7.27(2H,d,J=8.4Hz,3′,5′-H),6.79(2H,d,J=9.0Hz,2′,6′-H),4.85(1H,s, 13a-H), 4.58(1H, s, 13b-H), 4.20(1H, d, J=11.4Hz, 15a-H), 4.02(1H, m, 12a-H), 3.79(1H, m, 12b -H),3.50(1H,m,3-H),3.30(1H,d,J=10.2Hz,15b-H),2.88(2H,s,7-H),1.29(9H,s,t- Bu-H), 1.25(3H,s,16-H),0.67(3H,s,14-H). 13 C-NMR (150MHz, CDCl 3 ):δ156.7,147.3,143.1,126.1,126.1,113.8,113.8,107.2,80.6,67.0,64.1,55.2,52.5,42.8,38.9,38.0,36.7,34.0,31.5,31.5,31.5,28.2,24.0, 22.6, 15.1.
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