Pyrimido thiazole type compounds with anti-inflammatory effect and application thereof in preparation of anti-inflammatory medicaments
A compound, thiazole technology, used in anti-inflammatory agents, organic chemistry, drug combinations, etc.
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Embodiment 1
[0034] The synthesis of embodiment 1 compound
[0035] The preparation of intermediate 12-mercapto-4-methyl-6-phenyl-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester: in a 250ml round bottom flask with electromagnetic stirring, add 5.3g of benzaldehyde (0.05mol), 7.8g (0.06mol) of ethyl acetoacetate, 5.7g (00.75mol) of thiourea, 3.75g (0.04mol) of sulfamic acid, 50ml of absolute ethanol, heated to reflux for 2h, cooled, filtered, washed with water, After drying, 11.7 g of intermediate 1 was obtained, with a yield of 85%.
[0036] Preparation of the compound: In a 100ml round bottom flask with a reflux condenser and drying tube, add 0.552 g of ethyl 2-mercapto-4-methyl-6-phenyl-1,6-dihydro-pyrimidine-5-carboxylate g (0.002mol), ethyl chloroacetate 0.244g (0.002mol), pyridine 0.18g (0.002mol), absolute ethanol 10ml, reflux for 4h, then add aromatic aldehyde or heterocyclic aldehyde 0.002mol, piperidine or morpholine 0.17 g (0.002mol), continue to reflux for 4h, cool the reac...
Embodiment 2
[0044] Inhibition of the compound of Example 2 on the release of inflammatory factors from macrophages stimulated by LPS
[0045] The preliminary anti-inflammatory activity of the compound in vitro was tested by using the compound to inhibit the release of inflammatory factors (TNF-α and IL-6) from RAW264.7 macrophages stimulated by LPS. The specific method is as follows: 1.2×10 6 RAW264.7 macrophages were cultured with DMEM medium at 37°C. After 24 hours, the medium was renewed, and the test compound (final concentration: 10 μM) was added for pretreatment for 2 hours, and then treated with 0.5 μg / mL LPS for 22 hours. hours, collect the culture fluid and use ELISA method to detect the content of TNF-α and IL-6; collect the cells to detect the total protein concentration, the ELISA results are divided by the corresponding total protein concentration, and the TNF-α and IL-6 in the LPS control group The content was calibrated to 100; each compound was tested three times, and the ...
Embodiment 3
[0046] Example 3 The dose-effect relationship of the active compound inhibiting the release of inflammatory factors from macrophages stimulated by LPS
[0047] The dose-effect relationship of active compounds inhibiting the release of TNF-α and IL-6 from RAW264.7 macrophages stimulated by LPS was further tested. The method was the same as in Example 2. For experimental data, see image 3 . The inhibitory activities of the compounds on TNF-α and IL-6 all have a good dose-effect relationship, among which compound H19 shows a good dose relationship, and its inhibitory rate IC50 on IL-6 and TNF-α reached 0.83 μM respectively and 4.17μM, but compound H23 had no significant dose-dependent relationship.
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