Chrysin nitrogen-containing derivative as well as preparation method and purpose thereof

A kind of derivative, the technology of chrysin, which is applied in the application field of the nitrogen-containing derivative of chrysin, can solve the problems of poor water-solubility and fat-solubility, reduced activity, difficult to reach the action site and the like

Inactive Publication Date: 2010-07-14
JIANGSU POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chrysin is currently used as a second-line anticancer drug in clinical practice. Its anticancer effect is weaker than that of 5-fluorouracil and cisplatin, and its effect on some solid tumors is not obvious.
And clinically because of its poor water-solubility and fat-solubility, intestinal absorption is very little and the 5, 7 hydroxyl groups are easily glycosylated in vivo, resulting in reduced activity (Kroon PA, Clifford MN, Crozier A, et al.How should we assess the effects of exposure to dietary polyphenols invitro [J]. Am J Clin Nutr, 2004, 80(1): 15-21)
The only dosage form used in clinical trials is emulsion, which has poor stability. Intravenous administration has obvious vascular irritation, and it is difficult to reach the site of action, which limits its clinical application.

Method used

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  • Chrysin nitrogen-containing derivative as well as preparation method and purpose thereof
  • Chrysin nitrogen-containing derivative as well as preparation method and purpose thereof
  • Chrysin nitrogen-containing derivative as well as preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1 bromochrysin intermediate preparation of

[0025] Chrysin (500mg, 1.96mmol), 1,2-dibromoethane (3mL, 0.035mol), K 2 CO 3 (544mg, 3.93mmol), acetone 35mL, heated to reflux for 24h. The solvent was evaporated under reduced pressure and 50 mL of water was added to the system, and the K 2 CO 3 Dissolved and filtered to obtain a light yellow crude product, which was recrystallized from absolute ethanol to obtain a light yellow solid powder. FAB-MS, m / z: 362 (M+1); 1 H NMR (CDCl 3 , 500MHz) δ: 3.84~3.86 (2H, t, J=10.5Hz, OCH 2 C H 2 ), 4.46~4.48 (2H, t, J=10.5Hz, OCH 2 ), 6.43(1H, s, H-6), 6.88(1H, s, H-8), 7.06(1H, s, H-3), 7.58~7.65(3H, m, H-4', 5' , 6'), 8.10~8.12(2H, m, H-2', 3'); 13 C NMR (CDCl 3 , 500MHz) δ: 30.7 (OCH 2 C h 2 ), 68.4 (CH 2 ), 93.4(C-8), 98.5(C-6), 105.1(C-3), 105.3(C-10), 126.4(C-2', 6'), 129.0(C-3', 5' ), 130.5(C-4'), 132.1(C-1'), 157.2(C-9), 161.2(C-5), 163.5(C-2), 163.8(C-7), 182.0(C- 4)

Embodiment 2

[0026] Embodiment 2 bromochrysin intermediate preparation of

[0027] Chrysin (500mg, 1.96mmol), 1,6-dibromohexane (0.598mL, 3.92mmol), K 2 CO 3 (544mg, 3.93mmol), acetone 35mL, heated to reflux for 24h. The solvent was evaporated under reduced pressure and 50 mL of water was added to the system, and the K 2 CO 3 Dissolved and filtered to obtain a light yellow crude product, which was recrystallized from absolute ethanol to obtain a light yellow solid powder. FAB-MS, m / z: 417 (M+1); 1 H NMR (CDCl 3 , 500MHz) δ: 1.38~1.42 (2H, m, H-4"), 1.44~1.58 (2H, m, H-3"), 1.78~1.82 (2H, m, H-5"), 2.22~2.38 (4H, m, H-2", 6"), 4.12 (2H, t, J=10.8Hz, H-1"), 6.43 (1H, s, H-6), 6.89 (1H, s, H- 8), 7.05(1H, s, H-3), 7.57~7.63(3H, m, H-4', 5', 6'), 8.12~8.14(2H, m, H-2', 3') ; 13 C NMR (CDCl 3, 500MHz) δ: 25.2(C-3”), 28.3(C-4”), 29.8(C-2”), 32.5(C-5”), 33.6(C-6”), 68.8(C-1 ”), 93.5 (C-8), 98.4 (C-6), 105.1 (C-3), 105.3 (C-10), 126.4 (C-2’, 6’), 129.0 (C-3’, 5 '), 130.5(C-4'), 132.1...

Embodiment 3

[0028] Embodiment 3 bromochrysin intermediate preparation of

[0029] Chrysin (500mg, 1.96mmol), 1,20-dibromoeicosane (1.03g, 2.35mol), K 2 CO 3 (544mg, 3.93mmol), acetone 45mL, heated to reflux for 24h. The solvent was evaporated under reduced pressure and 50 mL of water was added to the system, and the K 2 CO 3 Dissolved and filtered to obtain a light yellow crude product, which was recrystallized from absolute ethanol to obtain a light yellow solid powder. FAB-MS, m / z: 613 (M+1); 1 H NMR (CDCl 3 , 500MHz) δ: 1.28~1.32 (32H, m, H-3”~H-18”), 1.71~1.76 (4H, m, H-2”, 19”), 3.28~3.31 (2H, t, J =9.6Hz, H-20"), 3.93~3.95 (2H, t, J=9.7Hz, H-1"), 6.44 (1H, s, H-6), 6.88 (1H, s, H-8) , 7.06(1H, s, H-3), 7.58~7.66(3H, m, H-4', 5', 6'), 8.09~8.11(2H, m, H-2', 3'); 13 C NMR (CDCl 3 , 500MHz) δ: 26.2 (C-2”), 28.2 (C-18”), 28.9 (C-17”), 29.6 (C-3”~C-16”), 32.8 (C-19”), 33.9(C-20"), 68.9(C-1"), 93.4(C-8), 98.6(C-6), 105.1(C-3), 105.3(C-10), 126.4(C-2' , 6'), 129.0(C-3', 5'), 1...

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Abstract

The invention discloses a chrysin nitrogen-containing derivative. Nitrogen-containing groups are introduced to a chrysin structure to synthesize the chrysin nitrogen-containing derivative with a novel structure. The molecular structure of the chrysin nitrogen-containing derivative is shown as (I), wherein R represents fatty amidogens of C1-C20, aromatic amidogens of C6-C20, heterocycle-containing amidogens of C1-C20 and alcohol amidogens or benzyl amidogens of C1-C20, and n represents the carbon chains of C2-C20. The derivative can have the biological activities of some similar alkaloids and simultaneously enlarge polarities, and the synthesized derivative presents a certain alkalinity, which is convenient to achieve the purpose of improving the water solubility with inorganic acid or organic acid finished salts.

Description

Technical field: [0001] The present invention relates to a novel nitrogen-containing chrysin derivative and a preparation method thereof, an intermediate for synthesizing the nitrogen-containing chrysin derivative and a preparation method thereof, and an application of the nitrogen-containing chrysin derivative. Background technique: [0002] Chrysin (Chrysin), chemical name 5,7-dihydroxyflavone is a kind of flavonoid compound extracted from the plant of Bignoniaceae plant Oryx chinensis, which has a wide range of pharmacological effects, such as anti-oxidation, anti-virus, anti-hypertension, hypoglycemic and inhibition of aromatase activity, especially its role in tumor prevention and treatment (Yuedong, Zhu Jiansi. Antitumor effects of chrysin and its derivatives [J]. Medical Theory and Practice, 2006, 19(10): 1155 -1157). At present, chrysin is used as a second-line anticancer drug in clinical practice. Its anticancer effect is weaker than that of 5-fluorouracil and cisp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/352A61P35/00
Inventor 胡昆任杰王炜程虹潘莎莎
Owner JIANGSU POLYTECHNIC UNIVERSITY
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