A kind of isatin core double spiro compound with antitumor activity and its synthesis method

A compound and general formula technology, applied in antitumor drugs, organic chemistry, drug combination and other directions, can solve problems such as treatment failure, and achieve the effect of few steps, high yield and good antitumor activity

Active Publication Date: 2017-02-22
SHAANXI UNIV OF SCI & TECH
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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 isatin core double spiro compound with antitumor activity and its synthesis method
  • A kind of isatin core double spiro compound with antitumor activity and its synthesis method
  • A kind of isatin core double spiro compound with antitumor activity and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Investigate the influence of different solvent systems on the yield of synthetic compound (1-2), the results are shown in Table 1:

[0050]

[0051] The reaction conditions are: the molar ratio of pulegone, isatin derivatives and sarcosine is 1:1:1, the reaction temperature is 80°C, the reaction time is 8 hours, and the solvents are toluene, ethyl acetate, ethanol and water respectively. , the results show that the yield of ethanol is the most ideal 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: the molar ratio of pulegone, isatin derivatives and sarcosine is 1:1:1, ethanol is used as solvent, the reaction temperature is 80°C, and the reaction time is 8 hours. Tungstic acid (H 3 PW 14 o 4 ), organic acid—acetic acid, Lewis acid—zinc chloride (ZnCl 2 ), the organic base-triethylamine as the catalyst, the molar ratio of the amount of the catalyst to the feeding amount of pulegone is 0.1 (that is, 0.1 times the equivalent), the results show that under the catalysis of heteropolyacid-phosphotungstic acid better 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 as follows: the molar ratio of pulegone, isatin 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 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 discloses a compound shown in a structural general formula (I) in the Specification and a synthesis method thereof. The double-spiro compound containing the isatin mother nucleus uses pulegone, isatin and derivatives thereof, and sarcosine as raw materials, and the synthesis process uses a one-pot method, so that complicated multi-step operations are avoided, the operation is simple and convenient, the reaction conditions are mild, and the yield is better. The bioactivity tests show that the double-spiro compound containing the isatin mother nucleus has better antineoplastic activity.

Description

technical field [0001] The invention relates to a synthesis method and antitumor biological activity of a class of isatin core-containing double spiro compounds, 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 , which in turn causes abnormal expression levels, transforming target cells and forming malignant tumors. 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 anti-tumor drugs with low toxicity and side effects has alway...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/10A61P35/00
CPCC07D487/10
Inventor 梁承远宋慧慧常相娜
Owner SHAANXI UNIV OF SCI & TECH
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