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15-(14-deoxy 11,12 dehydro) andrographolide carbonic side derivate and preparation process thereof

A technology of ester carbon glycoside derivatives and andrographolide, applied in the field of carbon glycoside compounds and preparation thereof, can solve the problems such as no reports of C15-andrographolide carbon glycoside derivatives, and achieves simple and convenient preparation method, resource Rich, high-yield effects

Inactive Publication Date: 2007-07-18
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research on andrographolide has become a focus of attention, but there is no report of C15-andrographolide carboside derivatives

Method used

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  • 15-(14-deoxy 11,12 dehydro) andrographolide carbonic side derivate and preparation process thereof
  • 15-(14-deoxy 11,12 dehydro) andrographolide carbonic side derivate and preparation process thereof
  • 15-(14-deoxy 11,12 dehydro) andrographolide carbonic side derivate and preparation process thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: prepare R shown in general formula 1 1 =(β-D-4-chloro-4-deoxy-galactosyl-1-)-methyl, R 2 = methyl, R 3 = R 4 = Derivative when H

[0017] 14-deoxy-11, 12-dehydroandrographolide 680mg, (β-D-4-chloro-4-deoxy-galactosyl-1-)-acetone 238mg dissolved in 10ml of methanol, adding 50mg of sodium carbonate, 65 °C for 6 hours. After the reaction, add 16 ml of chloroform to dilute, add silica gel to the suction filter funnel and filter to remove the alkali in the system, concentrate the reaction system, and separate by column chromatography to obtain 414 mg of light yellow solid, which is a pair of cis-trans isomerism mixture, cis / trans = 1 / 1, yield 75%. The experimental data are as follows:

[0018] C 29 h 41 ClO 8 .IR3391, 2935, 1744, 1077, 1031cm -1 ; 1 H NMR (400MHz, DMSO, TMS): δ8.01(s, 1H), 7.80(s, 1H,), 6.76(dd, 2H, J=10.4, 15.6Hz), 6.16(dd, 2H, J=12.8 , 15.6 Hz), 5.37(w, 2H, OH), 5.19(w, 2H, OH), 5.07(w, 2H, OH), 4.78(w, 2H, OH), 4.78(s, 2H), 4.44(...

Embodiment 2

[0019] Embodiment 2: prepare R shown in general formula 2 1 = (β-D-xylosyl-1-)-methyl, R 2 = methyl, R 3 = R 4 = Derivative when H

[0020] 14-deoxy-11,12-dehydro-8,17 epoxyandrographolide 600mg, (β-D-xylosyl-1-)-acetone 190mg dissolved in 10ml ethanol, add 60mg sodium bicarbonate, 70℃ React for 6 hours. After the reaction, add 16 ml of chloroform to dilute, add silica gel to the suction filter funnel and filter to remove the alkali in the system, concentrate the reaction system, and separate by column chromatography to obtain 427 mg of light yellow solid, which is a pair of cis-trans isomerism mixture, cis / trans = 1 / 1, 82% yield. The experimental data are as follows:

[0021] C 28 h 40 o 9 .IR3410, 2933, 1748, 1038em -1 ; 1H NMR (400MHz, DMSO, TMS): δ7.92(s, 0.5H), 7.80(s, 0.5H), 6.30(m, 1H), 6.08(m, 1H), 5.02(w, 4H, OH) , 4.12(w, 1H, OH), 3.81(d, 1H, J=10.9Hz), 3.63(m, 1H), 3.38-3.17(6H, overlap), 3.16(m, 1H), 3.06(m, 1H ), 2.90(m, 1H), 2.65(m, 2H), 2.45(m, 1H),...

Embodiment 3

[0022] Example 3: Preparation of R1=(β-D-galactosyl-1-)-methyl group shown in general formula 1, R 2 = methyl, R 3 = R 4 =CH 2 time derivative

[0023] 14-deoxy-11,12-dehydro-3,19-formal andrographolide 650mg, (β-D-galactosyl-1-)-acetone 220mg dissolved in 10ml of acetonitrile, added 50mg of triethylamine, 70 °C for 6 hours. After the reaction, the reaction system was concentrated and separated by column chromatography to obtain 426 mg of light yellow solid, which was a pair of cis-trans isomerism mixture, cis / trans=1 / 1, yield 78%. The experimental data are as follows:

[0024] C 30 h 42 o 9 .IR3400, 2939, 1753, 1445, 1026cm -1 ; 1 H NMR (400MHz, CDCl 3 , TMS): δ7.41(s, 1H), 7.32(s, 1H), 6.90(m, 1H), 6.14(d, 1H, J=15.6Hz), 4.90(s, 2H), 4.78(s, 2H), 4.29(s, 2H), 4.26-3.42(14H, overlap), 2.01(s, 3H), 1.41(s, 3H), 0.92(s, 3H); 13 C NMR (100.6 MHz, CDCl 3 , TMS): δ169.7, 148.8, 147.3, 147.1, 132.6, 132.3, 127.9, 127.7, 122.9, 110.3, 88.5, 87.3, 83.1, 81.0, 80.6, 79.9...

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Abstract

The present invention relates to carbon glycoside compound, and is especially 15-(14-deoxy-11, 12-dehydro)-andrographolide carbon glycoside derivative and its preparation process. The preparation process includes dewatering andrographolide as precursor compound, epoxidation and other reaction to obtain serial andrographolide derivatives; dissolving the derivatives and beta- carbon glycoside ketone in organic solvent and condensation reaction at certain temperature in the presence of catalyst for certain time. The derivative is significant in developing andrographolide.

Description

technical field [0001] The invention relates to a carbon glycoside compound and a preparation method thereof, in particular to a carbon glycoside derivative of andrographolide and a preparation method thereof. Background technique [0002] Carbon glycosides are a kind of glycoside compounds with a relatively special structure, and their sugar groups are directly connected to aglycones by C-C bonds. The research on glycosides in the past few decades mainly revolves around O-, S- and N-glycosides, while carbon glycosides are relatively less studied due to their analytical complexity. In recent years, with the gradual recognition of the biological activity of carbon glycosides, the research on carbon glycosides has become a research hotspot in the field of glycochemistry and biochemistry. [0003] Andrographolide is a diterpene lactone compound extracted from Andrographis paniculata (Bum.f.) Nees, a plant of the family Acanthaceae. It is one of the main components of Andrograp...

Claims

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Application Information

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IPC IPC(8): C07H15/26A61K31/7048
Inventor 刘宏民严琳徐海伟王俊峰赵明礼
Owner ZHENGZHOU UNIV
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