Preparation of a quinoline derivative and its application in anti-inflammation
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A technology of derivatives and quinolines, applied in the field of preparation and application of quinoline derivatives, to achieve good correlation, good inhibitory activity, and strong inhibitory effect
Active Publication Date: 2019-08-27
GUANGDONG UNIV OF TECH
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However, it has been found in clinical use that NSAIDs generally have adverse reactions such as cardiovascular, gastrointestinal, renal and hepatic damage.
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Embodiment 1
[0034] Example 1: Synthesis of compound A2, B2, C2, D2, E2, F2, G2
[0035] 1:1.5 Aniline and ethyl acetoacetate are catalyzed by polyphosphoric acid and reacted at 130°C for 2h. After the reaction, it was cooled to room temperature, crushed ice was added, and the pH was adjusted to 8 with sodium hydroxide. The solid was precipitated, filtered with suction, dried by infrared, and put directly into the next step without purification.
[0036]
Embodiment 2
[0037] Example 2: Synthesis of Compound A3-A17
[0038]
[0039] 1:1 equivalent of benzyl bromide and A2 solution DMF, add 5 equivalents of potassium carbonate, and react at room temperature for 8 hours. After the reaction, it was extracted with ethyl acetate and water, the organic phase was collected, and purified by silica gel column to obtain a white solid with a yield of 87-93%.
Embodiment 3
[0040] Example 3: Synthesis of Compound A18-A32
[0041]
[0042] Dioxane was used as a solvent, and A3-A17 of 1:1.5 equivalent was reacted with selenium dioxide at 65° C. for 2 hours. After the reaction, it was filtered, the filtrate was collected, and purified by a silica gel column. The yield was 71-85%.
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Abstract
The present invention belongs to the field of pharmaceuticals and chemical industry, and discloses preparation of a quinoline-based derivative based on topoisomerase I inhibition, and uses of the quinoline-based derivative as an anti-inflammatory drug, wherein the structural formula of the quinoline-based derivative is represented by a formula (I), R1 is hydrogen, fluorine, chlorine, bromine, iodine, methoxy, methyl, trifluoromethyl, nitro and nitrile, R2 and R3 respectively are hydrogen, chlorine, bromine, iodine, methoxy, methyl, trifluoromethyl, nitro and nitrile, R4 is carboxyl, methyl, phenyl, cyano and hydrogen, n is 0, 1, 2 and 3, and X is CH or N. According to the present invention, the quinoline-based derivative can remarkably inhibit the activity of human DNA topoisomerase I, provides significant inhibition effects in inflammations, and has broad application space in the preparation of anti-inflammatory drugs. The formula (I) is defined in the specification.
Description
Technical field [0001] The invention relates to the fields of medicine and chemical industry, and relates to the preparation and application of quinoline derivatives. Background technique [0002] Inflammation refers to the defensive response of living tissues with vascular system to injury factors. The main symptoms of inflammation are fever, redness, and pain. The mechanism is quite complicated. It is generally believed that immune cells aggregate to the lesion under the action of chemokines and release a large amount of inflammatory mediators, which leads to inflammation. Bacteria, viruses, rickettsiae, mycoplasma, fungi, spirochetes and parasites are the most common causes of inflammation. [0003] There are two types of drugs for treating inflammation: one is steroidal anti-inflammatory drugs, that is, the glucocorticoid hydrocortisone secreted by the adrenal cortex and its synthetic derivatives; the other is non-steroidal anti-inflammatory drugs (NSAIDs). , Non-steroid-anti...
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