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Troxerutin amide derivative as well as synthetic method and use thereof

A technology of troxerutinamide and rubutinamide is applied in the field of medicinal chemistry and achieves the effects of easy post-processing, mild reaction conditions and simple reaction process

Inactive Publication Date: 2017-09-15
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Catalyzed synthesis of troxerutinamide derivatives by ionic liquids has not been reported

Method used

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  • Troxerutin amide derivative as well as synthetic method and use thereof
  • Troxerutin amide derivative as well as synthetic method and use thereof
  • Troxerutin amide derivative as well as synthetic method and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0034] Weigh 140mg (0.18mmol) of troxerutin, 138mg (0.75mmol) of divinyl glutarate, and 10mL of pyridine in a 50mL Erlenmeyer flask, add 120mg of subtilisin, and put it in a constant temperature shaker at 50°C Reaction, speed 250rev·min -1 . After 72 hours of reaction, the enzyme was removed by filtration, and pyridine was distilled off under reduced pressure. Separation and purification by column chromatography, the eluent was ethyl acetate / methanol / water (15:3.6:0.5V / V), to obtain 103 mg (0.12 mmol) of troxerutin glutaryl vinyl ester as a yellow solid, with a yield of 65%.

[0035] 1 H-NMR (DMSO-d 6 ), δ(ppm): 12.49(s,1H,OH 5 ),7.85(s,1H,H 2’ ),7.74(d,1H,J=7.2Hz,H 6’ ),7.22(dd,1H,J=6.4Hz,J=14.1Hz,-OCH=),7.17(d,1H,J=6.6Hz,H 5’ ),6.75(s,1H,H 8 ),6.38(s,1H,H 6 ),5.35(d,1H,J=7.6Hz,H 1 ”),4.89(m,1H,OCH=CH 2 ),4.65(m,1H,OCH=CH 2 ),4.47(m,3H,2H of A acylated,1H of B acylated),4.32(m,1H,H 1 "'),4.26(m,1H,H of B acylated),4.12-4.05(m,4H,H of A),3.75(m,4H,H of B),3.71-3.0...

Embodiment 1-2

[0039] Add 95 mg (0.11 mmol) of troxerutin glutaryl vinyl ester, 153 mg (1.10 mmol) of 4-fluorophenethylamine, [OMIM] Br (1-n-octyl-3-methylimidazole) into a 50 mL Erlenmeyer flask Bromide) 10mL, oscillating in an air bath at 50°C at 150rpm at a constant temperature, and reacted for 24h. Extracted with ethyl acetate, concentrated under reduced pressure, separated and purified by column chromatography, the eluent was ethyl acetate / methanol / water (20 / 3 / 1, v / v), to obtain 4-fluorophenethylamine Rutinamide derivatives. Pale yellow solid 91.4 mg, yield 85%.

[0040] yellow powder,R f =0.3, 1 H NMR (400MHz, DMSO-d 6 +D 2 O,δppm):7.82-7.83(m,1H,H 2’ ),7.66-7.73(m,1H,H 6’ ),7.00-7.19(m,5H,1H of H 5’ ,5H of phenethylamine),6.66-6.68(m,1H,H 8 ),6.35-6.36(m,1H,H 6 ),5.32-5.37(m,1H,H 1 ”),4.35-4.38(m,3H,2H of Aacylated,1H of B acylated),4.24-4.28(m,2H,1H of H 1 " ’ ,1H of B acylated),4.02-4.08(m,4H,H of A),3.67-3.76(m,4H,H of B),3.01-3.76(m,12H,10H ofrhamnoglucosyl,2H of phen...

Embodiment 1-3

[0042] Weigh 140mg (0.18mmol) of troxerutin, 180mg (0.75mmol) of divinyl azelate, and 10mL of pyridine in a 50mL Erlenmeyer flask, add 175mg of subtilisin, and put it in a constant temperature shaker at 60°C Reaction, speed 250rev·min -1 . After 148 hours of reaction, the enzyme was removed by filtration, and pyridine was distilled off under reduced pressure. Post-processing is the same as above. 101 mg (0.10 mmol) of troxerutin vinyl azelate was obtained as a yellow solid with a yield of 57%.

[0043] 1 H-NMR (DMSO-d 6 ),δ(ppm):12.50(s,1H,OH 5 ),7.85(s,1H,H 2’ ),7.75(d,1H,J=8.4Hz,H 6’),7.21(dd,1H,J=6.0Hz,J=13.8Hz,-OCH=),7.15(d,1H,J=8.4Hz,H 5’ ),6.75(s,1H,H 8 ),6.38(s,1H,H 6 ),5.41(d,1H,J=10.0Hz,H 1” ),4.91(m,1H,OCH=CH 2 ),4.61(m,1H,OCH=CH 2 ),4.41(m,3H,2H of A acylated,1H of B acylated),4.32(m,1H,H 1”’ ),4.26(m,1H,H of B acylated),4.12-4.06(m,4H,H of A),3.75(m,4H,H of B),3.71-3.00(10H,Hof rhamnoglucosyl),2.39( t,2H,J=7.2Hz,-CH 2 -COOCH=CH 2 ),2.34(t,2H,J=7.2H...

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Abstract

The invention discloses a troxerutin amide derivative as well as a synthetic method and use thereof, belonging to the medicinal chemistry field. The method comprises the step of respectively reacting troxerutin vinyl ester as a raw material with a 1,2,3,4-tetrahydroisoquinoline compound or phenylethylamine, 4-fluoro-phenylethylamine and a benzylamine compound at 40-70 DEG C in ionic liquid, so as to obtain the troxerutin amide derivative. The troxerutin amide derivative has anti-tumor activity. The ionic liquid simultaneously serving as a solvent and a catalyst is utilized for synthesizing the troxerutin amide derivative, so that reaction conditions are mild, the operation is simple, the synthetic cost is low, the yield is relatively high, and a new way is provided for the structural modification of flavonoid compounds.

Description

technical field [0001] The invention relates to flavonoid compounds, in particular to troxerutinamide compounds, their preparation method and application, and belong to the field of medicinal chemistry. Background technique [0002] Flavonoids are polyphenolic compounds that are widely found in roots, stems, leaves, flowers, and fruits of higher plants. These compounds not only have good inhibitory and analgesic effects on cardiovascular, cerebrovascular, and digestive system abnormalities, but also It has the functions of scavenging free radicals, anti-tumor, anti-virus, anti-oxidation, anti-mutation, antibacterial and immune regulation (Harborne, JB; Williams, CA. Advances in flavonoid research since 1992[J]. Phytochemistry, 2000, 55, 481- 504; Liu Xingyu, Sun Tijian, Zhou Min. Pharmacological activity and separation and extraction of natural flavonoids [J]. Chinese Medicine and Clinic, 2014, 14(5), 621-624). However, due to its rigid planar structure and tight arrangemen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07A61P35/00C12P19/60
CPCC07H17/07C12P19/60Y02P20/54
Inventor 肖咏梅毛璞杨硕烨杨亮茹屈凌波袁金伟
Owner HENAN UNIVERSITY OF TECHNOLOGY
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