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Synthetic method of deguelin ring-breaking structure and amino acid derivatives with antitumor effect

A technology of anti-tumor effect and synthesis method, which is applied in the field of synthesis of deguerin ring-broken structure and amino acid derivatives, can solve the problems of less research on chemical transformation, and achieve low toxicity targeting, strong water solubility, and toxic and side effects small effect

Active Publication Date: 2018-01-12
GUANGZHOU GENERAL HOSPITAL OF GUANGZHOU MILITARY COMMAND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, domestic and foreign scholars have mostly studied deguerin in pharmacological aspects, and there are few studies on its chemical transformation.

Method used

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  • Synthetic method of deguelin ring-breaking structure and amino acid derivatives with antitumor effect
  • Synthetic method of deguelin ring-breaking structure and amino acid derivatives with antitumor effect
  • Synthetic method of deguelin ring-breaking structure and amino acid derivatives with antitumor effect

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1 (preparation method of product 5A)

[0058] 1. Add 2,4-2 hydroxybenzaldehyde (attached to the round bottom flask) figure 1 The indicated compound 2) 1g, Ca(OH) 2 0.514g, methanol 150mL. Then prenaldehyde was added dropwise (attached figure 1 The indicated compound 1) 3.045g. Stir at room temperature for 12h. Quench with HCl (1M) until pH 1–2. Methanol was evaporated off and the aqueous phase was extracted with 3*150 mL ethyl acetate. The organic phase was washed with 2*100 mL saturated brine, anhydrous Na 2 SO 4 Dry, filter under reduced pressure, and spin dry. The crude product was passed through a silica gel column (petroleum ether: ethyl acetate = 9:1), crystallized to obtain figure 1 The indicated product 3 (0.68 g).

[0059] 2. Put K in a round bottom flask 2 CO 3 2.43g, and with N 2 Protect. Dissolve 31.7976 g of the compound obtained in the previous step in anhydrous acetone, and add it into the reaction vessel with a syringe. Add dr...

Embodiment 2

[0061] Embodiment 2 (preparation method of product 5B)

[0062] 1. Add 2,4-2 hydroxybenzaldehyde (attached to the round bottom flask) figure 1 The indicated compound 2) 1g, Ca(OH) 2 0.514g, methanol 150mL. Then prenaldehyde was added dropwise (attached figure 1 The indicated compound 1) 3.045g. Stir at room temperature for 12h. Quench with HCl (1M) until pH 1–2. Methanol was evaporated off and the aqueous phase was extracted with 3*150 mL ethyl acetate. The organic phase was washed with 2*100mL saturated brine, anhydrous Na 2 SO 4 Dry, filter under reduced pressure, and spin dry. The crude product was passed through a silica gel column (petroleum ether: ethyl acetate = 9:1), crystallized to obtain figure 1 The indicated product 3 (0.68 g).

[0063] 2. Put K in a round bottom flask 2 CO 3 2.43g, and with N 2 Protect. Dissolve 31.7976 g of the compound obtained in the previous step in anhydrous acetone, and add it into the reaction vessel with a syringe. Add dro...

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Abstract

The invention discloses a synthetic method of antitumor deguelin broken-ring structure and amino acid derivative. The antitumor deguelin broken-ring structure and amino acid derivative has a following structural formula, wherein R is side-chain groups of amino acid; the synthetic method includes: 1), condensing 3-methylcrotonaldehyde and 2,4-2-hydroxybenzaldehyde under alkali catalysis condition; 2), methylating a product of step 1) with a methylation reagent under alkali catalysis condition; 3), subjecting a product of step 2) to reductive amination with amino acid to obtain a final product. The application of the deguelin broken-ring structure and amino acid derivative in the preparation of antitumor drugs is also disclosed. Deguelin is structurally modified with amino acid to synthesize a drug that has the advantages of high efficiency, low toxicity, targeting property and the like, the drug is highly water-soluble and low toxic and side effect and provides significant inhibitory action for the proliferation of tumor cells, particularly the proliferation of lung cancer cells.

Description

technical field [0001] The invention belongs to the fields of natural medicinal chemistry and antitumor compounds, and in particular relates to a synthesis method of a ring-broken structure of deguelin and amino acid derivatives with antitumor effects. Background technique [0002] Lung cancer is one of the malignant tumors with the fastest increasing morbidity and mortality and the greatest threat to the health and life of the population. Despite decades of dedicated efforts to treat lung cancer, the five-year survival rate for lung cancer remains below 20%. With the development of industry and economy, the improvement of people's living standards, and the increasingly serious problems of environmental pollution, the incidence of lung cancer has increased year by year, especially in economically developed areas. The number of lung cancer patients has doubled. Prevention and treatment of lung cancer have become clinical and scientific research important question. [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58A61P35/00
CPCC07D311/58
Inventor 吴新荣姜志辉孙婧雯吴碧娟谭翠雯
Owner GUANGZHOU GENERAL HOSPITAL OF GUANGZHOU MILITARY COMMAND