Dehydroabietic acid benzimidazole derivatives with antitumor activity as well as preparation method and application of dehydroabietic acid benzimidazole derivatives

A technology of dehydroabietic acid and benzimidazoles, which is applied in the fields of antineoplastic drugs, organic chemistry, and drug combinations, and can solve problems such as killing cells, infection, and bleeding

Inactive Publication Date: 2017-12-22
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs usually act on a certain target of cancer cells to prevent cell division and proliferation, but at the same time, these agents can also kill normal cells that proliferate rapidly, causing infection, bleeding and other symptoms

Method used

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  • Dehydroabietic acid benzimidazole derivatives with antitumor activity as well as preparation method and application of dehydroabietic acid benzimidazole derivatives
  • Dehydroabietic acid benzimidazole derivatives with antitumor activity as well as preparation method and application of dehydroabietic acid benzimidazole derivatives
  • Dehydroabietic acid benzimidazole derivatives with antitumor activity as well as preparation method and application of dehydroabietic acid benzimidazole derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Synthesis of Dehydroabietic Acid Benzimidazole Derivatives I-a

[0076] (1) dehydroabietic acid undergoes methyl esterification, bromination and double nitration reactions to obtain 12-bromo-13,14-dinitrodeisopropyl dehydrogenation methyl ester II;

[0077] (2) 12-bromo-13,14-dinitro-deisopropyl dehydroabietic acid methyl ester II is reduced by Fe / HCl to obtain 12-bromo-13,14-diamino-deisopropyl dehydroabietic acid methyl Ester III;

[0078] (3) In a three-necked flask, dissolve 0.66g (1.4998mmol) of 12-bromo-13,14-diaminodeisopropyl dehydroabietic acid methyl ester III in 30mL of absolute ethanol, and then add Add 0.24g (2.21mmol) of benzaldehyde, and then add 25.8mg (0.1499mmol) of p-toluenesulfonic acid. At 85°C, the mixture is stirred and refluxed for 24h under the protection of nitrogen. After the reaction, ethanol is removed by distillation under reduced pressure. Solvent, then want to add distilled water in the distillation residue, after extracting with ethyl ...

Embodiment 2

[0082] The difference between embodiment 2 and embodiment 1 is:

[0083] Synthesis of Dehydroabietic Acid Benzimidazole Derivatives I-b

[0084] In step (3), in a three-necked flask, 0.66 g (1.4998 mmol) of 12-bromo-13,14-diaminodeisopropyl dehydroabietic acid methyl ester III was dissolved in 30 mL of absolute ethanol, Then, 0.32 g (2.21 mmol) of indole-5-carboxaldehyde was added to the mixed solution, and then 25.8 mg (0.1499 mmol) of p-toluenesulfonic acid was added. At 85°C, the mixed solution was stirred and refluxed for 24 hours under the protection of nitrogen, and the reaction After the end, remove the ethanol solvent by distillation under reduced pressure, then add distilled water to the distillation residue, extract 2-3 times with ethyl acetate, then wash the organic phase with distilled water and saturated sodium chloride solution successively, and finally dry it over anhydrous sodium sulfate. Distill under reduced pressure, concentrate the organic phase, separate ...

Embodiment 3

[0088] The difference between embodiment 3 and embodiment 1 is:

[0089] Synthesis of Dehydroabietic Acid Benzimidazole Derivatives I-c

[0090] In step (3), in a three-necked flask, 0.66 g (1.4998 mmol) of 12-bromo-13,14-diaminodeisopropyl dehydroabietic acid methyl ester III was dissolved in 30 mL of absolute ethanol, Then, 0.32 g (2.21 mmol) of phenindole aldehyde was added to the mixed solution, and 25.8 mg (0.1499 mmol) of p-toluenesulfonic acid was added. At 85°C, the mixed solution was stirred and refluxed for 24 hours under the protection of nitrogen. After the reaction was completed, , remove the ethanol solvent by distillation under reduced pressure, then add distilled water to the distillation residue, extract 2-3 times with ethyl acetate, wash the organic phase with distilled water and saturated sodium chloride solution successively, and finally dry it with anhydrous sodium sulfate, Distill, concentrate the organic phase, separate and purify by silica gel column c...

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Abstract

The invention discloses dehydroabietic acid benzimidazole derivatives with antitumor activity as well as a preparation method and an application of the dehydroabietic acid benzimidazole derivatives. The dehydroabietic acid benzimidazole derivatives I-a to I-l with the structures shown in a general formula I and pharmaceutically acceptable salt of the derivatives are shown in the description, wherein corresponding Aryl of dehydroabietic acid benzimidazole derivatives I-a to I-l are shown in the description respectively. Nitrogen-containing heterocyclic compounds are pharmaceutically acceptable salt of the dehydroabietic acid benzimidazole derivatives and have good antitumor bioactivity. Pharmacology experiments prove that the compounds have a remarkable inhibition effect on hepatoma cell lines SMMC-7721, breast cancer cell lines MDA-MB-231 and colon cancer cell lines CT26.

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 derivatives with antitumor activity and a preparation method and application thereof. Background technique [0002] Tumor is a disease that seriously endangers human health. It has attracted more and more attention from all over the world and has become a major problem in the medical field. So far, it has not been treated fundamentally. Chemotherapy is one of the main methods for the treatment of tumor diseases, and anticancer drugs are now a major focus and hot spot in drug research and development. These drugs usually act on a certain target of cancer cells to prevent cell division and proliferation, but at the same time, these agents can also kill normal cells that proliferate rapidly, causing symptoms such as infection and bleeding. Therefore, the development of tumor suppressor drugs with high selectivity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61P35/00
CPCC07J73/008
Inventor 谷文陶徐兵苗婷婷金晓燕陈浩耿艺王石发
Owner NANJING FORESTRY UNIV
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