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Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof

A technology of dehydroabietic acid and benzimidazole, applied in the field of dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives and its preparation, can solve the problems of killing cells, infection, bleeding, etc., and achieve novel structure Effect

Active Publication Date: 2016-01-06
EFFEPHARM (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conventional method of tumor treatment is mainly chemotherapy, that is, cytotoxic agents such as DNA synthesis inhibitors or cell division inhibitors are used to inhibit tumor cells, but at the same time, these agents will also kill normal cells that proliferate rapidly, causing infection, bleeding and other symptoms

Method used

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  • Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof
  • Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof
  • Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof

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preparation example Construction

[0031] The preparation method of the dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives having the structure shown in general formula I of the present invention comprises the following steps:

[0032] (1) dehydroabietic acid obtains dehydroabietic acid methyl ester through acyl chloride, methyl esterification reaction, has the structure shown in general formula III:

[0033]

[0034] (2) Methyl dehydroabietate is brominated by NBS to obtain methyl dehydroabietate 12-bromo, which has a structure shown in general formula IV:

[0035]

[0036] (3) 12-bromodehydroabietic acid methyl ester is double-nitrated with fuming nitric acid to obtain 12-bromo-13,14-dinitrodeisopropyl dehydromethyl ester, which has the structure shown in general formula V:

[0037]

[0038] (4) 12-bromo-13,14-dinitro deisopropyl dehydroabietic acid methyl ester is reduced by Fe / HCl to obtain 12-bromo-13,14-diamino deisopropyl dehydroabietic acid methyl ester, which has Structure...

Embodiment 1

[0048] Synthesis of Methyl Dehydroabietate (III)

[0049] In a 500mL three-necked round-bottom flask, dissolve 30g (0.1mol) of dehydroabietic acid in 100mL of benzene, slowly add 10.9mL of thionyl chloride (0.15mol) and heat to reflux for 3h. After the reaction, remove the reaction solution under reduced pressure Benzene and excess thionyl chloride to obtain dehydroabietic acid chloride as yellow oil. Add 60mL of methanol into the bottle, heat to reflux for 3h, after the reaction, remove the solvent under reduced pressure, and recrystallize from ethanol to obtain white needle-like crystals which are methyl dehydroabietate (30.63g, 97.6%), m.p.62.3~63.9℃ .

Embodiment 2

[0051] Synthesis of 12-bromodehydroabietic acid methyl ester (IV)

[0052] Dissolve 15g of methyl dehydroabietate in 100mL of dry acetonitrile, then add 12g of NBS to the mixed solution, and react in the dark for 24 hours at room temperature, evaporate the solvent acetonitrile under reduced pressure, and add 100mL of carbon tetrachloride while hot , after cooling, filter out the insolubles in the solution, evaporate the solvent carbon tetrachloride under reduced pressure, dissolve it with anhydrous methanol, and recrystallize to obtain 10.5 g of white needle-like crystals, which is 12-bromodehydroabietic acid methyl Ester, yield 67%, m.p.133.5~135.7℃.

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Abstract

The invention discloses dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and a preparation method therefor and an application thereof. The invention discloses a dehydroabietic acid benzimidazole Schiff base heterocyclic derivative which has a structure shown in a formula I and pharmaceutically acceptable salt thereof (the formula is shown in the description), wherein the formula is shown in the description. The dehydroabietic acid benzimidazole Schiff base heterocyclic derivative and the pharmaceutically acceptable salt thereof have remarkable anti-tumor activity. Pharmacological experiments show that the dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives have remarkable inhibitory effect on human liver cancer cells HepG2 and SMMC-7721 and the effect of the derivatives is equivalent to positive control etoposide. The derivatives and salt thereof have the potential of developing anti-tumor drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with antitumor activity, a preparation method and application thereof. Background technique [0002] According to statistics, 1.5 million people die from cancer every year in my country, ranking first in the cause of death. Tumor has become one of the major malignant diseases with the highest mortality rate in the world. The conventional method of tumor treatment is mainly chemotherapy, that is, cytotoxic agents such as DNA synthesis inhibitors or cell division inhibitors are used to inhibit tumor cells, but at the same time, these agents will also kill normal cells that proliferate rapidly, causing infection, Symptoms such as bleeding. Therefore, the development of tumor suppressor drugs with high selectivity, good safety and high efficacy is an important direction of mode...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00C07J75/00A61P35/00
Inventor 谷文苗婷婷金晓燕王石发王霜
Owner EFFEPHARM (SHANGHAI) CO LTD
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