A kind of 7-azaisatin double spiro compound with antitumor activity and its synthesis method

A technology of compound and heteropolyacid, which is applied in the field of medicine, can solve problems such as treatment failure, and achieve the effect of less steps, high yield and good anti-tumor activity

Active Publication Date: 2017-01-25
SHENYANG HONGQI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mechanism of action of anti-tumor drugs and the targets of drugs are various, and the multi-drug resistance of tumor cells often leads to the failure of treatment.

Method used

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  • A kind of 7-azaisatin double spiro compound with antitumor activity and its synthesis method
  • A kind of 7-azaisatin double spiro compound with antitumor activity and its synthesis method
  • A kind of 7-azaisatin double spiro compound with antitumor activity and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The influence of different solvent systems on the yield of the synthesized compound (1-2) was investigated, and the results are shown in Table 1:

[0050]

[0051] The reaction conditions are: the molar ratio of pulegone, 7-azaisatin derivative and sarcosine is 1:1:1, the reaction temperature is 80°C, the reaction time is 10 hours, and the solvents are toluene and ethyl acetate respectively. , ethanol and water, the results show that the yield of ethanol is the best under the condition of no catalyst.

Embodiment 2

[0053] Taking the synthetic compound (1-2) as an example, the influence of different catalyst ratios on the yield of the target product was investigated, and the results are shown in Table 2:

[0054]

[0055] The reaction conditions are as follows: the molar ratio of pulegone, 7-azaisatin derivatives and sarcosine is 1:1:1, ethanol is used as solvent, the reaction temperature is 80°C, and the reaction time is 10 hours. Polyacid - phosphotungstic acid (H 3 PW 14 o 4 ), organic acid—acetic acid, Lewis acid—zinc chloride (ZnCl 2 ), the organic base - triethylamine, the molar ratio of the amount of catalyst to the amount of pulegone is 0.1 (that is, 0.1 times the equivalent), the results show that the reaction can be better under the catalysis of heteropoly acid - phosphotungstic acid yield.

Embodiment 3

[0057] Taking the synthetic compound (1-2) as an example, the influence of different reaction temperatures on the yield of the target product was investigated, and the results are shown in Table 3:

[0058]

[0059] The reaction conditions are: the molar ratio of pulegone, 7-azaisatin derivative and sarcosine is 1:1:1, ethanol is used as solvent, phosphotungstic acid is used as catalyst, the reaction time is 8 hours, and the reaction temperature is respectively 25°C, 60°C, 70°C, and 80°C. The results showed that the yield was the highest when the reaction temperature was 80°C (reflux temperature).

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Abstract

The invention relates to a 7-aza isatin nuclear parent-containing dispirocyclic compound with antitumor activity and shown as a structural formula (I) and a synthetic method thereof. The dispirocyclic compound is synthesized from raw materials of pulegone, 7-aza isatin and its derivatives, and sarcosine through a one-pot synthesis process; and the process avoids complicated multi-step operation, and has the advantages of mild reaction condition and good yield. Biological activity tests show that the 7-aza isatin nuclear parent-containing dispirocyclic compound has good antitumor activity and broad application prospects in the field of medicine.

Description

technical field [0001] The invention relates to a class of double spiro compounds containing a 7-azaisatin mother nucleus and a synthesis method thereof, belonging to the technical field of medicine. Background technique [0002] Tumor is a disease that seriously threatens human health, and tumor is essentially a genetic disease. DNA damage induced by various environmental and genetic carcinogens in a coordinated or sequential manner, resulting in the activation of proto-oncogenes and / or the inactivation of tumor suppressor genes, coupled with alterations in apoptosis-regulating genes and / or DNA repair genes , and then cause abnormal expression levels, transform target cells, and form malignant tumors, mainly due to unreasonable diet, genetic factors, environmental factors, etc. The mechanism of action of anti-tumor drugs and the targets of drugs are various, and the multi-drug resistance of tumor cells often leads to the failure of treatment. Finding effective and safe an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/20A61P35/00A61P35/04
CPCC07D471/20
Inventor 梁承远宋慧慧张诗韵毛跟年
Owner SHENYANG HONGQI PHARMA
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