Triazolonaphthyridine-one derivative compound and preparation method and application thereof
A technology of azonaphthyridinones and compounds, which is applied in the field of drug synthesis, can solve the problems that the activities of naphthyridinyl rings and corresponding derivative compounds have not been reported yet, and achieve the effect of simple method, high biological activity and easy operation
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Embodiment 1
[0030]2-(4-Hydroxy-3-methoxyphenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine-5-(3H) - Ketone (I-1)
[0031]
[0032] 2-(4-Hydroxy-3-methoxyphenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine- 5-(3H)-ketone can be prepared by the following method:
[0033] 2,3-Diamino-4-phenyl-2,7-naphthyridin-1-(2H)-one (2g, 8mmol) and 4-hydroxy-3-methoxybenzaldehyde (1.28g, 8.4mmol ) into the four-neck flask reactor, and then add 30mL of high-boiling point polar organic solvent N,N-dimethylformamide, and raise the temperature to 120°C under stirring for 25 hours for substitution reaction. After the reaction, cool down, and then, Carry out vacuum distillation to remove the solvent to dryness to obtain the residue crude product 2-(4-hydroxy-3-methoxyphenyl)-10-phenyl-[1,2,4]triazole[1,5-b] [2,7] Naphthyridin-5-(3H)-one, then add 10mL isopropanol solvent to the residue, heat up to dissolve, then slowly cool down to room temperature and stir for crystallization for 20 minutes...
Embodiment 2
[0041] 2-(4-Methylphenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridin-5-(3H)-one (I- 2)
[0042]
[0043] 2-(4-methylphenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine-5-(3H) in this example - Ketones can be prepared by the following methods:
[0044] Add 2,3-diamino-4-phenyl-2,7-naphthyridin-1-(2H)-one (2 g, 8 mmol) and 4-methylbenzaldehyde (0.96 g, 8 mmol) into a four-neck flask Then add 30 mL of high-boiling point polar organic solvent N,N-dimethylacetamide to the reactor, raise the temperature to 140°C under stirring for 20 hours to carry out the substitution reaction, after the reaction is completed, lower the temperature, and then carry out vacuum distillation to remove the solvent To dryness, the residue crude product 2-(4-methylphenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine-5-( 3H)-ketone, then add 10mL of absolute ethanol to the residue, heat up to dissolve, then slowly cool down to room temperature and stir for crystallization for 20 minu...
Embodiment 3
[0052] 2-(2,4-dichlorophenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridin-5-(3H)-one ( I-3)
[0053]
[0054] 2-(2,4-dichlorophenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine-5-( 3H)-ketones can be prepared by the following methods:
[0055] 2,3-Diamino-4-phenyl-2,7-naphthyridin-1-(2H)-one (2 g, 8 mmol) and 2,4-dichlorobenzaldehyde (1.40 g, 8 mmol) were added to tetra Then add 30 mL of high-boiling-point polar organic solvent N-methylpyrrolidone, and raise the temperature to 200 °C for 16 hours under stirring. After the reaction, cool down, and then carry out vacuum distillation to remove the solvent to dryness , to obtain the residue crude product 2-(2,4-dichlorophenyl)-10-phenyl-[1,2,4]triazol[1,5-b][2,7]naphthyridine-5-( 3H)-ketone, then add 15mL of absolute ethanol to the residue, heat up to dissolve, then slowly cool down to 10°C and stir for 20 minutes, a large amount of orange-yellow solid precipitates, then suction filtered and dried to obtain the pu...
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