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Synthetic method of ginkgo leaf polyprenol metal complex with light-operated activity

A technology of ginkgo biloba polyprenol and metal complexes, applied in the direction of organic active ingredients, pharmaceutical formulas, medical preparations of non-active ingredients, etc., to achieve the effect of good dark stability

Active Publication Date: 2021-01-22
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on the synthesis of GBP-ruthenium polypyridine metal complexes is rarely reported at home and abroad.

Method used

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  • Synthetic method of ginkgo leaf polyprenol metal complex with light-operated activity
  • Synthetic method of ginkgo leaf polyprenol metal complex with light-operated activity
  • Synthetic method of ginkgo leaf polyprenol metal complex with light-operated activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthetic route of aminopolypentenol is as figure 1 shown.

[0041] Weigh 0.27g of polyprenol, 0.06g of phthalimide and 0.11g of triphenylphosphine in a 35mL thick-walled pressure-resistant bottle, add 2.5mL of tetrahydrofuran, and then add 0.08g of diethyl azodicarboxylate Ester, reacted with magnetic stirring at 20°C for 4.0h (nitrogen atmosphere), concentrated after the reaction, the concentrate was dissolved in ether, after standing for a period of time, filtered to remove ether-insoluble substances, and concentrated ether solution to obtain 0.44g concentrate A, Concentrate A is light yellow oil, dissolve Concentrate A with a small amount of ether and then put it on a silica gel column (silica gel is 200-300 mesh, silica gel column is 2cm×40cm, 10g) for elution, eluent is ether: n-hexane Alkane=1:4, eluate A (0.21g) was light yellow oil, its Rf was 0.6 (developing solvent was diethyl ether:n-hexane=1:4);

[0042] Weigh 0.44g of eluate A and 0.24g of hydrazine ...

Embodiment 2

[0045] Weigh 30 mg of aminopolyprenol ligand, 11.3 mg of potassium hydroxide in 5 mL of water-ethanol (1:9) mixed solution, stir with a collector type constant temperature heating magnetic stirrer for 30 min, then add 100 mg of cis-Ru ( bpy) 2 Cl 2 , Reflux 2h. The solvent was removed by rotary evaporation to obtain 0.17 g of the concentrate. Then use a silica gel column for separation. Weigh 6g of silica gel, the silica gel column is 2cm×40cm, use 200-300 mesh silica gel, and rinse with eluent (chloroform-methanol=100:4). The collected compounds were dissolved in ethanol and NH 4 PF 6 Solid precipitated, filtered with filter paper to obtain a red precipitate, washed with water, and dried.

[0046] The hydrogen spectrum shift of aminopolyprenol metal complexes (such as image 3 shown) is parsed in two parts:

[0047] (1) Aminopolyprenol moiety 1 H NMR, δ: 5.27 (br-t,=C H -CH 2 -N); 5.12(m,=CH); 3.26(br-d,N-CH 2 ); 1.90~2.08(m,-CH 2 ); 1.71 (br-s,α-cis-CH 3 ); 1.6...

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Abstract

The invention discloses a synthetic method of a ginkgo leaf polyprenol metal complex with light-operated activity. The method comprises the following steps: taking high-purity ginkgo leaf polyprenol as a raw material, replacing terminal hydroxyl of polyprenol with an active group with stronger coordination ability by a chemical modification means, and then carrying out complexation reaction with aruthenium polypyridine complex to synthesize the ginkgo leaf polyprenol-ruthenium polypyridine metal complex. The prepared complex has good photoinduced dissociation efficiency and light-operated anti-tumor performance, and can provide theoretical reference and technical support for development of high-valued ginkgo leaf polyprenol functional products.

Description

technical field [0001] The invention belongs to the field of high-value functional product development of natural products, and in particular relates to a synthesis method of ginkgo biloba polyprenol metal complex with light control activity. Background technique [0002] Ginkgo biloba is a precious and unique forest source plant in my country. Ginkgo biloba has many important pharmacological effects and economic value, among which the main bioactive components are compounds such as flavonoids, terpene lactones, polyprenols (PPs) and polysaccharides. At present, the development and application of ginkgo biloba products in my country are still in the initial stage, and the flavonoids and terpene lactones are mainly used. The most valuable PPs have not yet been developed and utilized. Ginkgo biloba polyprenol (GBP) is a betulinic alcohol PPs composed of 14-24 isopentenyl units. It has become a research hotspot in recent years because of its similar structure to dolichol, whic...

Claims

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Application Information

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IPC IPC(8): C08G83/00A61P35/00A61K47/55A61K41/00A61K31/765A61K31/7135
CPCC08G83/008A61K41/0042A61K31/765A61K31/7135A61K47/55A61P35/00
Inventor 王成章张昌伟陶冉
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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