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Pyrazolo [3,4-b] quinoline compound and preparation method thereof
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A compound, the technology of phenylpyrazole, which is applied in the field of drug synthesis and achieves the effects of high yield, simple operation and high electronegativity
Inactive Publication Date: 2012-07-04
XINXIANG MEDICAL UNIV
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Many compounds containing pyrazolo[3,4-b]quinoline structures have been synthesized and have shown good biological activity, but for pyrazolo[3,4-b]quinones containing naphthoquinone and fluorine substitution Phenyl compound and synthetic method thereof, there is no report at present
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Embodiment 1
[0033] 1.73 g of 5-amino-3-methyl-1-phenylpyrazole, 1.24 g of p-fluorobenzaldehyde, 1.74 g of 2-hydroxy-1,4-naphthoquinone and 2 mL of [bmim]BF 4 Put them together in a 50 ml reaction bottle, mix well, stir at room temperature, and react for 2 hours. Add 10 mL of water to dilute, filter, and recrystallize with 95% ethanol to obtain the corresponding brown-red product 4,11-dihydro-4-(4-fluorophenyl)-3-methyl-1-phenyl- 3.52 g of 1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-dione is a brownish-red solid with a melting point of 272-273 degrees Celsius and a yield of 81%.
[0039] 1.73 g of 5-amino-3-methyl-1-phenylpyrazole, 1.36 g of p-fluorobenzaldehyde, 1.74 g of 2-hydroxy-1,4-naphthoquinone and 2 mL of [bmim]BF 4 Put them together in a 50 ml reaction bottle, mix well, stir at room temperature, and react for 2 hours. Add 10 mL of water to dilute, filter, and recrystallize with 95% ethanol to obtain the corresponding brown-red product 4,11-dihydro-4-(4-fluorophenyl)-3-methyl-1-phenyl- 1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-dione 3.61g, the yield is 83%; the experimental data of infrared, hydrogen spectrum, carbon spectrum and elemental analysis are the same as the implementation example 1.
Embodiment 3
[0041] 1.73 g of 5-amino-3-methyl-1-phenylpyrazole, 1.49 g of p-fluorobenzaldehyde, 1.74 g of 2-hydroxy-1,4-naphthoquinone and 2 mL of [bmim]BF 4 Put them together in a 50 ml reaction bottle, mix well, stir at room temperature, and react for 2 hours. Add 10 mL of water to dilute, filter, and recrystallize with 95% ethanol to obtain the corresponding brown-red product 4,11-dihydro-4-(4-fluorophenyl)-3-methyl-1-phenyl- 1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-dione 3.65g, the yield is 84%; the experimental data of infrared, hydrogen spectrum, carbon spectrum and elemental analysis are the same as the implementation example 1.
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Abstract
The invention relates to a 4,11-dihydro-4-(4-fluorophenyl)-3-methyl-1-phenyl-1H-benzo [h] pyrazolo [3,4-b] quinoline-5,10-dione compound. The compound has the following structural formula. The invention also relates to a preparation method for the compound, which comprises the following steps of: putting 5-amino-3-methyl-1-phenylparazole, p-fluorobenzaldehyde, 2-hydroxy-1,4-naphthoquinone and [bmim]BF4 ionic liquid into a reaction bottle together, stirring the solution at room temperature, reacting the solution for 2 to 3 hours, diluting the solution by using water, then filtering the solution, and re-crystallizing the filtrate to obtain 4,11-dihydro-4-(4-fluorophenyl)-3-methyl-1-phenyl-1H-benzo [h] pyrazolo [3,4-b] quinoline-5,10-dione. The compound has stronger activity and is more favorable for absorption; and the method has the characteristics of environmental protection, easily-obtained raw materials, simple operation and high yield.
Description
technical field [0001] The invention relates to the field of drug synthesis, in particular to a pyrazolo[3,4-b]quinoline compound and a preparation method thereof. Background technique [0002] Pyrazolo[3,4-b]quinoline compounds have a wide range of biological activities, such as antibacterial, antiviral, antitumor, and inhibition of cyclooxygenase activity. In addition, many pyrazolo[3,4-b]quinoline compounds have good optical properties and can be used in dyes, laser technology, and fluorescent materials. [0003] Naphthoquinone is an important class of compounds, which are widely used in organic synthesis, dye industry, and medicine. Fluorine-containing organic compounds are used in many drugs due to their unique physical, chemical properties and biological activities. Compounds, such as anticancer drugfluorouracil, fludarabine phosphate, antidepressantfluoxetine, weight lossdrug fluramine, etc. Many compounds containing pyrazolo[3,4-b]quinoline structures have been...
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