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7-benz[c]acridine(4-p-fluorophenyl)-1,2,3-triazole as well as preparation method and application thereof

A technology for p-fluorophenyl and benzo, which is applied in the field of condensed heterocyclic compound 7-benzo[c]acridine-1, to achieve the effects of high purity and yield, good medicinal value, and easy availability of raw materials

Inactive Publication Date: 2016-03-23
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, fluorine-containing drugs have the advantages of high biological activity, strong stability, and resistance to drug resistance. If 1,2,3-triazole structure and fluorine-containing groups are introduced into benzo[c]acridine , it is expected to obtain new anti-tumor drugs with high efficiency and low toxicity, but there are no relevant reports so far

Method used

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  • 7-benz[c]acridine(4-p-fluorophenyl)-1,2,3-triazole as well as preparation method and application thereof
  • 7-benz[c]acridine(4-p-fluorophenyl)-1,2,3-triazole as well as preparation method and application thereof
  • 7-benz[c]acridine(4-p-fluorophenyl)-1,2,3-triazole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of 7-benzo[c]acridine (4-p-fluorophenyl)-1,2,3-triazole, concrete steps are as follows:

[0025] Step 1, in a 250mL three-necked flask, add 5.20g (26mmol) o-bromobenzoic acid, 4.86g (34mmol) naphthylamine, 7.5g (36.2mmol) potassium carbonate and 0.3g (4.7mmol) copper powder, then add 30mL Isoamyl alcohol was used as a solvent, refluxed and stirred at 140°C for 2 hours, after the reaction, evaporated the solvent under reduced pressure, added 600mL of water to the obtained residue, stirred at 80°C for 20min, filtered while hot, washed the filter cake with water, combined the water layer, water The layer was acidified with concentrated hydrochloric acid to pH = 2, and a large amount of purple-black precipitate was precipitated, which was filtered with suction, and the obtained solid was recrystallized with ethanol to obtain compound 1 with a yield of 58%;

[0026] Step 2: In a 100mL round-bottomed flask, add 1.14g (4.3mmol) of compound 1 and 4.5mL of phosph...

Embodiment 2

[0035] Repeat Example 1, the difference is:

[0036] In step one, the consumption of potassium carbonate is 5.39g (26mmol), copper powder 0.17g (2.6mmol), the solvent is n-amyl alcohol, the temperature during reflux is 100°C, and the combined aqueous layer is acidified to pH with concentrated hydrochloric acid = 4;

[0037] In step 2, the temperature during the reaction is 100°C;

[0038] In Step 3, compound 2 was dissolved in acetonitrile solution, the amount of sodium azide was 0.26g (4mmoL), and the reaction temperature was 80°C;

[0039] In step 4, the volume ratio of tert-butanol and water in the tert-butanol aqueous solution is 4:6.

[0040] The isolated pale yellow needle-like crystals were analyzed by H-spectrum and carbon-spectrum, and determined to be 7-benzo[c]acridine(4-p-fluorophenyl)-1,2,3-triazole.

Embodiment 3

[0042] Repeat Example 1, the difference is:

[0043] In step 1, the temperature at reflux was 160°C, and the combined aqueous layer was acidified to pH=2 with concentrated hydrochloric acid;

[0044] In step 3, the dosage of sodium azide is 0.26g (4mmoL), and the temperature during the reaction is 100°C;

[0045] In step 4, the volume ratio of tert-butanol and water in the tert-butanol aqueous solution is 6:4, the reaction temperature is changed to 100° C., and the solvent for recrystallization is ethanol or chloroform.

[0046] The isolated pale yellow needle-like crystals were analyzed by H-spectrum and carbon-spectrum, and determined to be 7-benzo[c]acridine(4-p-fluorophenyl)-1,2,3-triazole.

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Abstract

The invention discloses a benz[c]acridine-1,2,3-triazole compound as well as a preparation method and application thereof. The preparation method of the 7-benz[c]acridine-1,2,3-triazole compound comprises the following steps: 1) taking o-bromobenzoic acid and naphthylamine as raw materials, potassium carbonate and copper powder as catalysts and isoamyl alcohol or n-amyl alcohol as a solvent to undergo Ullmann reaction to obtain a compound 1; 2) carrying out ring closure on the compound 1 with phosphorus oxychloride to prepare a compound 2; 3) dissolving the compound 2 in dimethyl fumarate to undergo nucleophilic substitution reaction with sodium azide to prepare a compound 3; and 4) dissolving p-fluorophenyl acetylene in a tert-butyl alcohol water solution, adding vitamin C sodium, anhydrous cupric sulfate and the compound 3 to react and carrying out suction filtration and recrystallization, thus obtaining the 7-benz[c]acridine-1,2,3-triazole compound.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a condensed heterocyclic compound 7-benzo[c]acridine(4-p-fluorophenyl)-1,2,3-triazole and its preparation method and application. Background technique [0002] Acridine is a class of nitrogen-containing organic heterocyclic compounds that has received extensive attention. It has shown strong physiological activities in anti-tumor, anti-virus, anti-malarial, anti-bacterial, bioluminescence probes and treatment of AIDS. At present, the benzo[c]acridine skeleton is less studied at home and abroad. Studies have shown that this type of compound has a strong growth inhibitory effect on L1210 cells, and individual derivatives inhibit IC 50 Reaching the nmol level, and the research on this kind of compound is limited to the 7-amino substituted derivatives, which greatly limits its further application. 1,2,3-triazole rings are often used as biological isosteres of amino groups and other ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61P35/00
CPCC07D401/04
Inventor 霍丽妮陈睿李培源苏炜曹立成
Owner GUANGXI UNIV OF CHINESE MEDICINE
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