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Nitrogenous troxerutin derivative, preparation method thereof and application

A technology for troxerutin and derivatives, which is applied in the field of medicinal chemistry and achieves the effects of easy post-processing, high regioselectivity and simple reaction process

Active Publication Date: 2012-10-10
伊诺药物研究南京有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the modification of troxerutin by enzyme catalysis and the preparation of nitrogen-containing troxerutin derivatives

Method used

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  • Nitrogenous troxerutin derivative, preparation method thereof and application
  • Nitrogenous troxerutin derivative, preparation method thereof and application
  • Nitrogenous troxerutin derivative, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0024] In a 100 mL Erlenmeyer flask, weigh 560 mg (0.75 mmol) of troxerutin, 582 mg (3 mmol) of divinyl adipate, and 20 mL of pyridine as a solvent, add 600 mg of Bacillus licheniformis alkaline protease, and put Put it into a constant temperature shaker at 50°C and react at a speed of 250 rev·min -1 . After 72 hours of reaction, the enzyme was removed by filtration, and pyridine was distilled off under reduced pressure. Use a mixed solvent of petroleum ether and chloroform with a volume ratio of 3:1 to wash away residual pyridine to obtain a brownish-yellow sticky solid, which is separated and purified by column chromatography, and the eluent is ethyl acetate / methanol / water (15:3.6:0.5 V / V), 403 mg (0.45 mmol) of troxerutin vinyl adipate was obtained as a yellow solid, and the yield was 60%.

[0025] 1 H-NMR (DMSO -d 6 ), δ (ppm): 12.49 (s, 1 H, OH 5 ), 7.84 (s, 1 H, H 2’ ), 7.73 (d, 1H, J=7.2 Hz, H 6’ ), 7.20 (dd, 1 H, J=6.24 Hz, J=14.0 Hz, -OCH=), 7.14 (d, 1 H, J=7....

Embodiment 1-2

[0029] Weigh 560 mg (0.75 mmol) of troxerutin, 756 mg (3 mmol) of divinyl sebacate, and 20 mL of pyridine in a 100 mL Erlenmeyer flask, add 600 mg of Bacillus licheniformis alkaline protease, and put Put it into a constant temperature shaker at 60°C and react at a speed of 250 rev·min -1 . After 120 h of reaction, the enzyme was removed by filtration, and pyridine was distilled off under reduced pressure. Purification as above. 400 mg (0.42 mmol) of troxerutin vinyl sebacoyl was obtained as a yellow solid with a yield of 56%.

[0030] 1 H-NMR (DMSO -d 6 ), δ (ppm): 12.49 (s, 1 H, OH 5 ), 7.84 (s, 1 H, H 2’ ), 7.72 (d, 1H, J=7.0 Hz, H 6’ ), 7.20 (dd, 1 H, J=6.21 Hz, J=14.0 Hz, -OCH=), 7.14 (d, 1 H, J=7.4 Hz, H 5’ ), 6.73 (s, 1 H, H 8 ), 6.38 (s, 1 H, H 6 ), 5.34 (d, 1 H, J=7.3 Hz, H 1’’ ), 4.89 (m, 1 H, OCH=CH 2 ), 4.63 (m, 1 H, OCH=CH 2 ), 4.39 (m, 3 H, 2 H of A acylated, 1 H of B acylated), 4.31 (m, 1 H, H 1’’’ ), 4.26 (m, 1 H, H of B acylated), 4.12-4.06 (m, 4...

Embodiment 1-3

[0034] Add 403 mg (0.45 mmol) of troxerutin vinyl adipate to a 50 mL Erlenmeyer flask, add 576 mg of 1-n-propylpiperazine according to a molar ratio of 1:10, add 25 mL of pyridine as a solvent, and add Lipase LS -10 After adding 600 mg of lipase, place it in a constant temperature shaker at 50°C for reaction at a speed of 250 rev·min -1 . After 120 h of reaction, the reaction was terminated. Post-processing is the same as above. The final product 242mg (0.248mmol) of the piperazine-containing troxerutin derivative was obtained as a yellow solid, and the yield was 55%.

[0035] 1 H-NMR (DMSO -d 6 +D 2 O), δ (ppm): 7.85 (s, 1 H, H 2’ ), 7.73 (d, 1 H, J=7.1 Hz, H 6’ ), 7.16 (d, 1 H, J=7.6 Hz, H 5’ ), 6.71 (s, 1 H, H 8 ), 6.36 (s, 1 H, H 6 ), 5.35 (d, 1 H, J=7.2 Hz, H 1’’ ), 4.40 (m, 3 H, 2 H of A acylated, 1 H of B acylated), 4.30 (m, 1 H, H 1’’’ ), 4.27 (m, 1 H, H of B acylated), 4.11-4.07 (m, 4 H, H of A), 3.75 (m, 4 H, H of B), 3.71-3.11 (10 H, H of rhamnoglucos...

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Abstract

The invention discloses a nitrogenous troxerutin derivative and a preparation method thereof, and belongs to the field of medicinal chemistry. In the method, troxerutin and divinyl ester are used as raw materials, organic solvents serve as reaction media under catalysis of hydrolytic enzyme, the reaction temperature ranges from 40 DEG C to 60 DEG C, troxerutin vinyl ester is obtained and serves as a substrate respectively reacting with dimethyldiguanide or piperazine compounds under enzyme catalysis, troxerutin derivatives containing triazine rings and piperazine rings are respectively obtained, and the compounds have antitumor activity. The preparation method is moderate in reaction condition and simple in operation, the enzyme can be recycled, and a good way is provided for nitrogenous derivatization of natural products.

Description

technical field [0001] The invention relates to flavonoid compounds, in particular to nitrogen-containing troxerutin derivatives and a preparation method thereof, belonging to the field of medicinal chemistry. Background technique [0002] Flavonoids are an important class of natural organic compounds, which widely exist in the roots, stems, leaves, flowers, and fruits of higher plants. They not only have a large number of types, but also have complex and diverse structures. class of secondary metabolites. Flavonoids have high chemical reactivity, can scavenge free radicals in organisms, and have antioxidant effects. On the other hand, flavonoids have many important pharmacological effects, and have therapeutic value for many human diseases, such as: anti-mutation, anti-aging, anti-tumor, antibacterial, etc. In addition, flavonoids are active ingredients of many Chinese herbal medicines such as skullcap and ginkgo. Although natural flavonoids exist in nature in large quan...

Claims

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Application Information

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IPC IPC(8): C07H17/07C12P19/60A61K31/706A61P35/00
Inventor 肖咏梅袁金伟杨亮茹王宏雁游利琴毛璞买文鹏
Owner 伊诺药物研究南京有限公司
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