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Preparation method and application of 5-aminobenzene[b][1,8]naphthyridine compound

A compound, aminobenzene technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of few synthesis and activity studies, no biological activity reported in the literature, etc., and achieve good inhibitory activity effect

Active Publication Date: 2019-10-08
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 5-Aminobenzo[ b ][1,8]Naphthyridine derivatives (Formula 1) are an important class of benzo[ b ][1,8]Naphthyridine compounds, its synthesis and activity studies are rarely reported
[0010] This is what has been seen so far about 2,4-dimethyl-5-aminobenzo[ b ][1,8]Naphthyridine derivatives have been synthesized, but the biological activity of these compounds has not been reported in the literature

Method used

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  • Preparation method and application of 5-aminobenzene[b][1,8]naphthyridine compound

Examples

Experimental program
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Embodiment 1

[0035] Example 1: Synthesis of compound 2a.

[0036] Compound 1a (10.0 g, 67.5 mmol) and POCl 3 (20 mL) were added to the round-bottomed flask successively, and the round-bottomed flask was placed in an oil bath at 110 °C, under N 2 Under protection, reflux and stir the reaction for 12 h (monitor the progress of the reaction with TLC, developing solvent: V 乙酸乙酯 : V 石油醚 = 1: 4), after the reaction is completed, cool to room temperature, and remove most of the POCl under reduced pressure 3 , slowly add ice water and saturated NaHCO 3 Solution, adjust the pH value of the solution to about 7, transfer the mixed solution to a 500mL separatory funnel, and use saturated NaHCO 3 solution (3×30 mL) and DCM extraction (5×30 mL), the organic phases were combined, washed 3–4 times with saturated NaCl, anhydrous NaCl 2 SO 4 Dry and concentrate under reduced pressure to obtain compound 2a , milky white powder, yield: 95%.

Embodiment 2

[0037] The synthesis of embodiment 2 compound 2b

[0038] with compound 1b Instead of compound 1a, the experimental operation steps refer to Example 1 to obtain compound 2b , Yield: 90%.

Embodiment 3

[0039] The synthesis of embodiment 3 compound 3aa

[0040] Add compound 2a sequentially in a 100 mL round bottom flask (0.7 g, 4.0 mmol), p-methylaniline (1.3 g, 12.0 mmol) and DMSO (15 mL), in N 2 Heat and stir the reaction in an oil bath at 120°C under protection (monitor the reaction progress with TLC, developing solvent: V 乙酸乙酯 : V 石油醚 = 1: 10). After the reaction is complete, cool to room temperature and wash with saturated NaHCO 3 solution (3×30 mL) and DCM solution (5×30 mL), combined the organic phases, washed with saturated NaCl solution 3 to 4 times, anhydrous NaCl 2 SO 4 Drying, concentration under reduced pressure, purification by silica gel column chromatography (eluent: V 乙酸乙酯 : V 石油醚 = 1: 45), to obtain compound 3aa , white powder, yield: 39%.

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Abstract

The invention belongs to the field of pharmaceutical chemistry, and specifically provides a preparation method and application of a 5-aminobenzene[b][1,8]naphthyridine compound. The preparation methodis a route for synthesis of the 5-aminobenzene [b][1,8] naphthalidine compound by intramolecular cyclization of a molecule of a 4,6-2-disubstituted-2-Naryl-3nitrile compound catalyzed by trifluoro-methanesulfonic acid, more 5-aminobenzene[b][1,8]naphthalidine compounds can be prepared, and the prepared compounds show good antitumor activity in vitro.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of 5-aminobenzo[b][1,8]naphthyridine compounds and the application of the compounds in the preparation of antitumor drugs. Background technique [0002] Malignant tumor is one of the most dangerous diseases that endanger human health, and it is also the second leading cause of death in the world. According to the latest report of the World Health Organization, nearly one-sixth of global deaths are caused by malignant tumors. In my country, the incidence of tumors has been increasing year by year, and the discovery of new anti-tumor lead compounds has very important research significance. [0003] 5-Aminobenzo[ b ][1,8]Naphthyridine derivatives (Formula 1) are an important class of benzo[ b ][1,8]Naphthyridine compounds, there are few reports on their synthesis and activity. [0004] [0005] Formula 1 5-aminobenzo[ b ][1,8]naphthyridine d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61P35/00
CPCA61P35/00C07D471/04
Inventor 黄婉云张晓婷郑彬吕良王淑琴
Owner GUILIN MEDICAL UNIVERSITY
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