Curcumin-containing aryl metal complexes as well as synthetic method and application thereof

A technology of aryl metals and synthesis methods, applied in the direction of metallocenes, organic chemical methods, osmium organic compounds, etc., can solve the problems of high toxicity and side effects, difficult metabolism, low bioavailability, etc., to improve bioavailability and process flow Simple, cell death-inducing effect

Active Publication Date: 2018-11-02
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a class of curcumin aryl metal complexes. On the one hand, the curcumin aryl metal complexes can solve the problem that curcumin is not easily soluble in water when it is used as an anticancer drug or an anticancer drug component. , poor stability and low bioavailability, on the other hand can also solve the problem of large toxic and side effects and difficult metabolism when simple aryl metal complex anticancer drugs or anticancer drug components exist; curcumin aryl of the present invention Metal complexes have good anti-cancer, anti-metastasis, and antibacterial activities while having low toxic and side effects

Method used

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  • Curcumin-containing aryl metal complexes as well as synthetic method and application thereof
  • Curcumin-containing aryl metal complexes as well as synthetic method and application thereof
  • Curcumin-containing aryl metal complexes as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Curcumin (18.40mg, 0.05mmol) and sodium methoxide (10.8mg, 0.20mmol) were dissolved in 20mL of methanol, stirred and reacted at room temperature for 1 hour; then dichloro(4-methylisopropylphenyl) Osmium(II) dimer (39.54mg, 0.05mmol) was added to the reaction tube (the mixed reaction material was reacted in the reaction tube), stirred and reacted at 48°C under reflux for 24h; In addition to the organic solvent, select a suitable eluent to separate and purify by column chromatography, place the separated and purified product for recrystallization in a refrigerator, and slowly precipitate to obtain orange-red crystals, collect the crystals, vacuum dry, weigh, Calculated yield: 68%.

[0040] Elemental analysis: Theoretical value (%): C 31 h 33 o 6 ClOs (CH 3 OH)·0.5(H 2 O): C50.02, H4.99; Experimental value: C49.84, H4.88. 1 H NMR (400MHz, DMSO) δ9.56(s, 2H), 7.41(d, J=15.6Hz, 2H), 7.24(d, J=1.7Hz, 2H), 7.06(dd, J=8.2, 1.7Hz , 2H), 6.81(d, J=8.1Hz, 2H), 6.56(d, J=15....

Embodiment 2

[0042] Curcumin (18.40mg, 0.05mmol) and potassium hydroxide (2.8mg, 0.05mmol) were dissolved in 15mL of ethylene glycol, stirred and reacted at room temperature for 0.5 hours; then dichloro(biphenyl)osmium(II ) dimer (33.23mg, 0.04mmol) was added to the reaction tube (the mixed reaction material was reacted in the reaction tube), stirred and reacted at 86°C under reflux for 17h; after the reaction was complete, the organic solvent was removed under reduced pressure distillation , select a suitable eluent to separate and purify by column chromatography, place the separated and purified product for recrystallization in a refrigerator, and slowly precipitate to obtain orange-red crystals, collect the crystals, vacuum dry, weigh, and calculate the yield For: 73%.

[0043] Elemental analysis: theoretical value (%) C 33 h 29 o 6 ClOs 0.5(CH 3 OH): C53.04, H3.91; Experimental value: C52.24, H3.87. 1H NMR (400MHz, DMSO) δ9.54(s, 2H, OH of curc), 7.78(dd, J=6.5, 3.1Hz, 2H, C(4,4')...

Embodiment 3

[0045] Curcumin (92.0mg, 0.25mmol) and sodium hydroxide (2.0mg, 0.05mmol) were dissolved in 20mL of dichloromethane, stirred and reacted at room temperature for 2 hours; then dichloro(biphenyl)ruthenium(II ) dimer (9.79mg, 0.015mmol) was added to the reaction tube (the mixed reaction material was reacted in the reaction tube), stirred and reacted at 25°C under reflux for 44h; after the reaction was complete, the organic solvent was removed under reduced pressure distillation , select a suitable eluent to separate and purify by column chromatography, place the separated and purified product for recrystallization in a refrigerator, and slowly precipitate to obtain orange-red crystals, collect the crystals, vacuum dry, weigh, and calculate the yield For: 80%.

[0046] Elemental analysis: theoretical value (%) C 33 h 29 o 6 C1Ru·0.5(CH 3 OH): C60.23, H4.44; found: C59.01, H 4.17. 1 H NMR (500MHz, CDCl 3 )δ7.81(dd, J=6.6, 2.7Hz, 2H, C(4,4')H of curc), 7.50(m, 3H, H bip ), 7....

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Abstract

The invention discloses curcumin-containing aryl metal complexes which can effectively improve bioavailability of curcumin and have good phototoxicity, anti-cancer activity, angiogenesis inhibiting capacity and antibacterial activity. The invention further discloses a synthetic method of the curcumin-containing aryl metal complexes. The method adopts simple technical process, is easy to operate and high in yield. The invention finally discloses an application of the curcumin-containing aryl metal complexes to preparation of anti-cancer drugs, anti-cancer drug components, anti-tumor metastasisdrugs, anti-tumor metastasis drug components, antibacterial agents and antibacterial agent components.

Description

technical field [0001] The present invention relates to a class of curcumin aryl metal complexes, and also relates to the synthesis method of the curcumin aryl metal complexes and their use in the preparation of anticancer drugs, anticancer drug components, anti-tumor metastasis drugs, anti-tumor metastasis Applications in pharmaceutical components, antimicrobials and components of antimicrobials. technical background [0002] The potential medicinal value of natural products has made the anti-tumor research of natural products gradually become a hot spot in clinical anti-tumor drug research. Curcumin is a class of active ingredients extracted from the rhizome of the ginger plant turmeric. Studies have shown that curcumin itself has biological activities such as lowering blood fat, anti-tumor, anti-inflammatory, choleretic, and antioxidant. The antioxidant activity and anti-inflammatory effect of curcumin are related to the occurrence of many diseases in the human body and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C07F15/00A61P35/04A61P35/00A61P31/10A61P31/04
CPCA61P31/04A61P31/10A61P35/00A61P35/04C07B2200/13C07F15/002C07F17/02
Inventor 刘红科郝元元苏志钱勇李季薛旭玲
Owner NANJING NORMAL UNIVERSITY
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