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Dehydroabietic acid indole derivative, preparation method and use thereof

A technology of indole derivatives and dehydroabietic acid, applied in the field of dehydroabietic acid indole heterocyclic derivatives and its preparation, to achieve good anti-tumor effect

Active Publication Date: 2016-05-25
兰州天禾生物催化技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The research on the anticancer activity of these compounds has not been reported at home and abroad

Method used

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  • Dehydroabietic acid indole derivative, preparation method and use thereof
  • Dehydroabietic acid indole derivative, preparation method and use thereof
  • Dehydroabietic acid indole derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 dehydroabietic acid methyl ester (III)

[0029] In a 500mL three-neck round bottom flask, 30g (0.1mol) of dehydroabietic acid was dissolved in 100mL of benzene, slowly added 10.9mL of thionyl chloride (17.85g, 0.15mol), and heated to reflux for 3h. After the reaction, benzene and excess thionyl chloride were distilled off to obtain yellow oily dehydroabietoyl chloride. Add 60mL of methanol to the bottle and heat to reflux for 2h. After the reaction, the solvent was distilled off, and the product was recrystallized from ethanol to obtain methyl dehydroabietate (28.9 g, 92%) in the form of white needles.

[0030] m.p.62.3-63.9℃,IR(KBr,cm -1 ):ν3052,2994,2930,2868,1721,1381,1250,1082,825. 1 HNMR (CDCl 3 ,300MHz):δ1.23(d,J=7.1Hz,6H,13-CH(CH 3 ) 2 ),1.27(s,3H,CH 3 ),1.42(m,1H),1.50(m,1H),1.57(s,3H,CH 3 ),1.61-1.70(m,5H),2.24(dd,J=12.5,2.1Hz,1H),2.30(d,J=12.3Hz,1H),2.80-2.90(m,3H),3.66(s, 3H, COOCH 3 ),6.88(d,J=1.5Hz,1H,H-14),6.99(dd,J=...

Embodiment 27

[0031] Synthesis of embodiment 27-carbonyl dehydroabietic acid methyl ester (IV)

[0032] Methyl dehydroabietate (8 g, 25.5 mmol) was dissolved in 30 mL of glacial acetic acid, and chromium trioxide (2.64 g, 26.4 mmol) was dissolved in 18 mL of acetic acid / acetic anhydride (1:2, v / v). Then, the chromium trioxide solution was slowly added dropwise to the methyl dehydroabietate solution at 0° C. with stirring, and the reaction solution was stirred overnight at room temperature. After the reaction, the reaction solution was poured into ice water, extracted three times with dichloromethane, the organic phases were combined, washed with saturated sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (petroleum ether / acetone 100:1, v / v) to give methyl 7-oxo-dehydroabietate (5.36 g, 64%) as a yellow oil.

[0033] 1 HNMR (...

Embodiment 3

[0034] Example 3 Synthesis of dehydroabietic acid indole derivatives (V)

[0035]1.8 g (5.5 mmol) of compound IV was dissolved in 20 mL of ethanol, 1.74 g (12 mmol) of phenylhydrazine hydrochloride and 2 mL of concentrated hydrochloric acid were added, and the reaction mixture was heated to reflux for 3 h. After the reaction, the mixture was poured into ice water, extracted three times with dichloromethane, the organic phases were combined, washed with saturated sodium bicarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (petroleum ether / acetone 50:1, v / v) to obtain compound V as a white powder (1.35 g, 61%).

[0036] mp170-172℃;IR(KBr,ν,cm -1 ):3370,2958,2930,2868,1700,1460,1441,1263. 1 HNMR (CDCl 3 ):1.10(s,3H,H-14),1.31(d,3H,J=7Hz,H-17orH-18),1.32(d,3H,J=7Hz,H-18orH-17),1.69(m ,1H),1.77(s,3H,H-15),1.80-2.00(m,4H),2....

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Abstract

The invention relates to the field of the organic synthesis and medicinal chemistry, and in particular relates to a dehydroabietic acid indole derivative, a preparation method of the dehydroabietic acid indole derivative and application of the dehydroabietic acid indole derivative in preparing anti-tumor medicaments. Pharmacology experiments show that the dehydroabietic acid indole derivative disclosed by the invention has a significant inhibiting effect on seven strains of tumor cells such as human liver cancer cells (Hep-1, Huh7), cervical cancer cells (HeLa), breast cancer cells (MCF7), colon cancer cells (Caco-2), gastric cancer cells (HGC-27) and lung cancer cells (HCC827), and has the values of developing the anti-tumor medicaments.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of dehydroabietic acid indole heterocyclic derivatives, a preparation method thereof and an antitumor application. Background technique [0002] Cancer is one of the major malignant diseases with the highest mortality rate in the world. According to statistics, 1.5 million people die from cancer every year in my country, ranking first in the cause of death. At present, chemotherapy is still one of the basic means of treating tumors. However, the existing chemotherapeutic drugs still have many deficiencies. This is mainly because the vast majority of anti-tumor drugs are anti-cell proliferation agents, such as alkylating agents, DNA-binding agents, etc., and their treatment is based on the fact that tumor cells have a higher proliferation rate, so they do not really selectively act on cancer cells. cell. This leads to the problem of low selecti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80A61K31/403A61P35/00
CPCC07D209/80
Inventor 谷文张广王石发
Owner 兰州天禾生物催化技术有限公司
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