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Podophyllotoxin-retinoic acid heterocomplex synthesis method and application of podophyllotoxin-retinoic acid heterocomplex in medicine for preventing and curing tumors

A technology of podophyllotoxin and retinoic acid, which is applied in the direction of antineoplastic drugs, drug combinations, and medical preparations containing active ingredients, and can solve problems such as adverse reactions and side effects of retinoic acid

Active Publication Date: 2017-08-01
ZUNYI MEDICAL UNIVERSITY
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Problems solved by technology

However, retinoic acid can produce certain adverse reactions and side effects

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  • Podophyllotoxin-retinoic acid heterocomplex synthesis method and application of podophyllotoxin-retinoic acid heterocomplex in medicine for preventing and curing tumors

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Embodiment 1

[0029] Example 1: Preparation of Podophyllotoxin-Retinoic Acid Hybrid (I)

[0030] Add 0.3 g (1 mmol) of retinoic acid (IV) into a 10 mL round bottom flask, add oxalyl chloride (1 mL) and toluene (5 mL), and stir at 25 °C for 2 hours. The solvent and unreacted reagents were removed under reduced pressure to obtain the intermediate tretinoyl chloride (III). Dissolve intermediate III in 5 mL of dichloromethane, add triethylamine (0.5 mL), stir well at 0 °C, add 0.414 g (1 mmol) of podophyllotoxin II, raise the temperature of the system to 25 °C, and continue stirring for 3~5 Hour. After the reaction was complete as monitored by TLC, water was added to quench the reaction, extracted three times with dichloromethane, washed once with saturated brine, and the organic phase was dried overnight with anhydrous magnesium sulfate. After filtration, the solvent was removed under reduced pressure, and the crude product was separated and purified by silica gel column chromatography to ob...

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Abstract

The invention relates to a podophyllotoxin-retinoic acid heterocomplex synthesis method and application of a podophyllotoxin-retinoic acid heterocomplex in a medicine for preventing and curing tumors. The podophyllotoxin-retinoic acid heterocomplex has a structural formula as shown in a formula I (shown in the description); a preparation method of the compound as shown in the formula (I) is as follows (shown in the description), wherein a to b represent reaction conditions: a: a reagent is oxalyl chloride, a solvent is methylbenzene, and reaction temperature is 20 to 35 DEG C; b: a solvent is dichloromethane, a catalyst is triethylamine, and reaction temperature is 10 to 30 DEG C. A solvate is a complex prepared from the compound as shown in the formula (I), ethyl alcohol, diethyl ether, n-butyl alcohol, water, acetone or an isopropanol solvent. An experimental result shows that the podophyllotoxin-retinoic acid heterocomplex has a strong inhibiting effect on two human gastric cancer cell strains, and has an IC50 value in a nano-mole level, which is remarkably better than that of positive control agents: retinoic acid and etoposide. The compound as shown in the general formula (I) has the highest antiproliferative activity on human gastric cancer BGC-823 cells, is used for preventing and curing cell proliferation abnormity related diseases, and is particularly applied in the medicine for preventing or curing the tumors.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a podophyllotoxin-retinoic acid hybrid, its preparation method and its use in preventing and treating diseases related to abnormal cell proliferation, especially in drugs for preventing or treating tumors. Background technique [0002] Podophyllotoxin is an aromatic lignin natural product mainly derived from the roots, stems or leaves of Podophyllum plants. Studies have shown that podophyllotoxin can prevent tubulin from forming the spindle and inhibit the mitotic process of cells, and has strong anti-tumor activity, which has attracted widespread attention from scholars at home and abroad. However, the high toxicity of podophyllotoxin greatly limits its clinical application. In order to reduce the toxic and side effects of podophyllotoxin, people have carried out a lot of modification work on its structure, and found anti-tumor drugs represented by etoposide and teniposide. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/365A61P35/00
CPCC07D493/04
Inventor 王京张磊
Owner ZUNYI MEDICAL UNIVERSITY
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