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Preparation of oxadiazole compound and application thereof to anti-inflammatory treatment

A technology of oxadiazoles and target compounds, applied in anti-inflammatory agents, organic chemistry, drug combination, etc.

Inactive Publication Date: 2013-05-08
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, autoimmune diseases and immune rejection are important diseases for troubled people, and taking common anti-inflammatory drugs will cause side effects such as nausea and vomiting

Method used

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  • Preparation of oxadiazole compound and application thereof to anti-inflammatory treatment
  • Preparation of oxadiazole compound and application thereof to anti-inflammatory treatment
  • Preparation of oxadiazole compound and application thereof to anti-inflammatory treatment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: 2-phenyl-3-acetyl-5-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1,3,4-oxa Preparation of Oxadiazole (Compound 5a)

[0024]

[0025] Take 0.0015moL of hydrazide and equimolar carbonyl compounds and add them to 50mL of round bottom burner, add 30mL of absolute ethanol and 7.5mL of water, heat to dissolve, add 0.3mL of glacial acetic acid, and reflux for 5h. After the reaction, it was poured into water, and the precipitated solid was filtered, washed with water, dried and then recrystallized by absolute ethanol to obtain Schiff's base. Take 0.001 mol of Schiff's base and equimolar benzaldehyde after drying and put them into a 25 mL round bottom flask, add 5 mL of acetic anhydride and 2 mL of glacial acetic acid, heat to reflux for 1 hour, pour into ice water after cooling, and stir until solids precipitate out , the precipitated solid was filtered, washed with water, dried and recrystallized with absolute ethanol to obtain pure compound 4a (white crystal). Yield...

Embodiment 2

[0026] Example 2: 2-(2-chlorophenyl) 3-acetyl 5-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1,3, Preparation of 4-oxadiazole (compound 5b)

[0027]

[0028] The preparation method is the same as in Example 1. The benzaldehyde in Example 1 was replaced with LinCl benzaldehyde to obtain the target compound in the form of white crystals. White crystal, Yield 69%, mp: 171-172°C, 1H NMR (300MHz, DMSO-d6) δ: 2.26(s, 3H), 4.29-4.30(m, 4H), 6.98(d, J=8.4Hz, 1H), 7.22(d, J=2.0Hz, 1H), 7.28-7.31(m, 2H), 7.41-7.51(m, 3H), 7.56(d, J=7.9Hz, 1H).MS(ESI): 359.8 (C 18 h 16 ClN 2 o 4 ,[M+H]+).Anal.Calcd for C 18 h 15 ClN 2 o 4 : C, 60.26; H, 4.21; N, 7.81. Found: C, 60.24; H, 4.21; N, 7.83.

Embodiment 3

[0029] Example 3: 2-(4-nitrophenyl)-3-acetyl-5-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1 , Preparation of 3,4-oxadiazole (compound 5c)

[0030]

[0031] The preparation method is the same as in Example 1. The benzaldehyde in Example 1 was replaced by p-nitrobenzaldehyde to obtain the target compound in the form of yellow crystals. Yield 60%; mp: 151-152°C 1H NMR (DMSO-d 6 , 300MHz): 2.25(s, 3H), 4.28-4.31(m, 4H), 7.01(d, J=8.40Hz, 1H), 7.27-7.31(m, 2H), 7.32-7.36(m, 1H), 7.76 (d, J=8.79Hz, 2H), 8.29 (d, J=8.61Hz, 2H). MS (ESI): 370.10 (C18H16N3O6, [M+H]+). Anal. Calcd for C18H15N3O6: C, 58.54 ; H, 4.09; N, 11.38; O, 25.99. Found: C, 58.53; H, 4.09; N, 11.40.

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Abstract

A kind of oxadiazole derivative is characterized by having a following formula, and R is shown as below. The oxadiazole derivative provided by the invention has obvious anti-inflammatory effect on ConA induced lymphocyte proliferation in mice. Therefore, the oxadiazole derivative provided by the invention can be used as a potential anti-inflammatory drug. The invention discloses the preparation method of the compound.

Description

technical field [0001] The invention relates to a class of oxadiazole derivatives, a preparation method thereof and an application as an anti-inflammatory drug. Background technique [0002] Immune disease refers to the disease caused by the imbalance of immune regulation and affects the immune response of the body, generally refers to autoimmune disease, and immune rejection is also an important type of immune disease. In recent years, autoimmune diseases and immune rejection are important diseases for troubled people, and taking common anti-inflammatory drugs will cause side effects such as nausea and vomiting. Therefore, it is an urgent task to find new compounds with effective anti-proliferation activity of liver cancer cells. [0003] In the immune system, T cells play a very important role. The normal function of T cells is the core of acquired cellular immunity, while the dysfunction of T cells can lead to a series of autoimmune diseases. Many studies have shown that...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A61P29/00
Inventor 朱海亮燕茹张志明张雪薇
Owner NANJING UNIV
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