A kind of dicarboxychalcone compound and its application in the preparation of anti-inflammatory drugs

A technology of chalcones and methylchalcones, which is applied in the preparation of oxygen-containing compounds, organic compounds, anti-inflammatory agents, etc., can solve the problem of selective antagonist research starting late and achieve obvious ear swelling , the effect of suppressing auricle swelling

Active Publication Date: 2021-01-12
CHINA JILIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In contrast, CysLT 2 The research on selective antagonists started late, and there is still no commercial CysLT 2 Antagonist, only the selective CysLT first reported by Bayer in 2010 2 Antagonistic active compound HAMI3379

Method used

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  • A kind of dicarboxychalcone compound and its application in the preparation of anti-inflammatory drugs
  • A kind of dicarboxychalcone compound and its application in the preparation of anti-inflammatory drugs
  • A kind of dicarboxychalcone compound and its application in the preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]Example 1 3-(4-phenoxybutoxy)-2'-carboxyethoxy-5'-carboxymethylchalcone (I-1)

[0044]

[0045] synthetic route:

[0046]

[0047] Synthesis of compound M1-1:

[0048] m-Hydroxybenzaldehyde (41.0mmol), 4-phenoxybutyl bromide (41.0mmol) and anhydrous potassium carbonate (82.0mmol) were dissolved in 200mL of acetone, heated to reflux for 8 hours, cooled, filtered to remove potassium carbonate, evaporated Acetone, and the residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1, v / v) to obtain a pale yellow liquid (80%). MS:270[M] + .

[0049] Synthesis of Compound M2-1:

[0050] 2-Methoxymethoxy-5-bromoacetophenone (38.8 mmol), ethyl acetoacetate (59.1 mmol), potassium phosphate (116.4 mmol), palladium acetate (0.4 mmol) and tri-tert-butylphosphine ( 0.08mmol) into 20mL of toluene, heated to 150°C under the protection of nitrogen, reacted for 24 hours, cooled to room temperature, extracted with ethyl acetate, washed with satu...

Embodiment 2

[0055] Example 2 3-(4-p-fluorophenoxybutoxy)-2'-carboxyethoxy-5'-carboxymethylchalcone (I-2)

[0056]

[0057] 1-(4-bromobutoxy)-4-fluorobenzene was substituted for 4-bromobutoxybenzene in Example 1, and the synthesis method was referred to Example 1 to obtain compound I-2, MS:535[M-H] - . 1 H-NMR (400Hz, DMSO-d 6 ):δ7.91(s,1H),7.68(d,1H),7.51(d,1H),7.33(m,3H),7.27(d,1H),7.15(d,1H),7.04(m, 2H),6.91(d,1H),6.86(d,2H),4.35(t,2H),4.00(t,2H),3.96(t,2H),3.51(s,2H),2.78(t,2H ), 1.93(m,4H).

Embodiment 3

[0058] Example 3 3-(4-p-chlorophenoxybutoxy)-2'-carboxyethoxy-5'-carboxymethylchalcone (I-3)

[0059]

[0060] 1-(4-bromobutoxy)-4-chlorobenzene was substituted for 4-bromobutoxybenzene in Example 1, the synthetic method was referred to Example 1, and compound I-3 was synthesized, MS:551[M-H] - . 1 H-NMR (400Hz, DMSO-d 6 ):δ8.02(s,1H),7.87(d,1H),7.75(d,1H),7.62(d,1H),7.55(d,2H),7.46(d,1H),7.21(d, 1H),7.17(m,2H),7.04(m,3H),4.54(t,2H),4.28(t,2H),4.21(t,2H),3.72(s,2H),3.00(t,2H ), 2.03(m,4H).

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Abstract

The invention discloses a dicarboxyl chalcone compound and an application of the dicarboxyl chalcone compound in preparation of an anti-inflammatory drug, and also discloses a novel pharmaceutical composition containing the novel dicarboxyl chalcone compound. The pharmaceutical composition comprises the dicarboxyl chalcone compound with a treatment effective amount or is pharmaceutically acceptable salt and a pharmaceutical composition of at least a pharmaceutically acceptable carrier. The dicarboxyl chalcone compound realizes selective antagonism on activity of a CysLT2 acceptor, and presentsgood anti-inflammatory activity in an in-vivo experiment, and the dicarboxyl chalcone compound is hopeful for being developed to the novel anti-inflammatory drug.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a specific dicarboxychalcone compound, the application of the compound in the preparation of anti-inflammatory drugs and drugs for treating inflammation-related diseases, and a preparation method of such compounds. Background technique [0002] During the inflammatory process, the inflammatory mediators derived from arachidonic acid have attracted much attention. Studies have shown that arachidonic acid is mainly metabolized by cyclooxygenases (COX) and lipoxygenases (LOX) to generate prostaglandins and leukotrienes and other inflammatory mediators. COX inhibitors represented by aspirin and ibuprofen are widely used clinically, but long-term use is prone to gastrointestinal, cardiovascular and other adverse reactions. In addition, the lipoxygenase pathway and its product leukotrienes play an important role in inflammation, including bronchitis, asthma and the inflam...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/90C07C27/02A61K31/194A61P29/00
CPCA61P29/00C07C59/90
Inventor 刘冠男
Owner CHINA JILIANG UNIV
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