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Acridine-1,3,4-thiadiazole compounds and their preparation methods and applications

A technology of thiadiazoles and compounds, applied in the field of medicine, to achieve the effects of increasing the conjugation area, good medicinal value, and improving binding ability

Active Publication Date: 2017-01-04
广西新桂环保科技集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there have been no relevant reports on acridine derivatives and their antitumor activity by introducing aromatic heterocyclic structures into acridine to obtain 1,3,4-thiadiazole rings

Method used

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  • Acridine-1,3,4-thiadiazole compounds and their preparation methods and applications
  • Acridine-1,3,4-thiadiazole compounds and their preparation methods and applications
  • Acridine-1,3,4-thiadiazole compounds and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of 2-(2-methyl-9-acridinimino)-3-p-methoxyphenyl-1,3,4-thiadiazole, the specific steps are as follows:

[0028] 1) In a 250ml three-necked flask, add 5.20g (26mmol) of o-bromobenzoic acid, 3.64g (34mmol) of p-methylaniline, 7.5g (36.2mmol) of potassium carbonate and 0.3g (4.7mmol) of copper powder, and then add 30ml of isoamyl alcohol was used as a solvent, and stirred under reflux at 140°C for 2h. After the reaction, evaporate the solvent under reduced pressure, add 600ml of water to the obtained residue, react at 80°C for 20 minutes, filter while hot, wash the filter cake, combine the water layer, acidify the water layer with concentrated hydrochloric acid to pH=2, and precipitate a large amount of light green Precipitation, suction filtration, and the obtained solid was recrystallized with chloroform to obtain compound 1 with a yield of 79%;

[0029] 2) In a 100ml round bottom flask, add 14.38g (18mmol) of the compound and 14.37ml of phosphorus oxych...

Embodiment 2

[0039] Repeat Example 1, the difference is:

[0040] In step 1), change the consumption of potassium carbonate to 5.39g (26mmol), copper powder 0.17g (2.6mmol), replace isoamyl alcohol with n-amyl alcohol, change the temperature during reflux to 150°C, and combine the water The layer was acidified to pH=1 with concentrated hydrochloric acid;

[0041] In step 3), the consumption of sodium thiocyanate is changed to 1.62g (20mmoL), the temperature during the reaction is changed to 80°C, and the organic solvent acetone is replaced with methanol;

[0042] In step 4), acetonitrile is used to replace the organic solvent absolute ethanol, and the temperature at reflux is changed to 60°C;

[0043] In step 5), 98% concentrated sulfuric acid was replaced with acetic acid.

[0044] The isolated orange-yellow solid was analyzed by mass spectrometry and carbon spectrometry, and it was determined to be 2-(2-methyl-9-acridinimino)-3-p-methoxyphenyl-1,3,4-thiadiene azole.

Embodiment 3

[0046] Repeat Example 1, the difference is:

[0047] In step 1), the temperature at reflux was changed to 160° C., and the combined aqueous layer was acidified to pH=4 with concentrated hydrochloric acid;

[0048] In step 3), the organic solvent acetone is replaced with a composition of methanol and acetonitrile (the volume ratio of methanol and acetonitrile is 1:1);

[0049] In step 4), the amount of p-methoxybenzohydrazide was changed to 0.99 g (6 mmol), and the organic solvent absolute ethanol was replaced with acetone.

[0050] The isolated orange-yellow solid was analyzed by mass spectrometry and carbon spectrometry, and it was determined to be 2-(2-methyl-9-acridinimino)-3-p-methoxyphenyl-1,3,4-thiadiene azole.

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Abstract

The invention discloses an acridine-1,3,4-thiadiazole compound, a preparation method and application thereof. The preparation of described acridine-1,3,4-thiadiazole compound comprises: 1) take o-bromobenzoic acid and p-methylaniline as raw material, potassium carbonate and copper powder as catalyst, with isoamyl alcohol or n-pentyl Alcohol is used as a solvent, and compound 1 is obtained by reaction; 2) compound 1 is obtained by ring-closing phosphorus oxychloride to obtain compound 2; 3) compound 2 is dissolved in an organic solvent and then reacted with thiocyanate in the presence of tetrabutylammonium bromide Compound 3 was obtained by sodium reaction; 4) Compound 3 was dissolved in an organic solvent and reacted with p-methoxybenzohydrazide to obtain Compound 4; 5) Compound 4 was reacted with concentrated sulfuric acid or acetic acid, and the reactant was added with water to form a solid. Suction filtration, that is to say. The results of in vitro anti-tumor tests showed that it had significant in vitro anti-tumor activity against MGC80‑3, BEL‑7404, NCI‑H460 and T24.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an acridine-1,3,4-thiadiazole compound, a preparation method and application thereof. Background technique [0002] DNA is an ideal biological target in the development of anti-tumor drugs, and DNA intercalators can be better embedded in the middle of DNA base pairs in the double helix, which provides a basis for the design of DNA-targeted anti-tumor drugs. [0003] Chromophore molecules with planar rigid structure often play an important role as DNA targeting molecules in the design and in vitro screening of antitumor drugs. Acridine is a class of nitrogen-containing organic heterocyclic compounds that has received widespread attention. Because its structure is a macrocyclic conjugated system with a rigid planar structure, it can be used as an intercalator for macromolecules such as DNA, and has anti-tumor, anti-virus, and anti-malarial , antibacterial, bioluminescent probes a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A61P35/00
Inventor 刘华钢霍丽妮
Owner 广西新桂环保科技集团有限公司
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