Synthesis and anti-inflammatory activity of S-oxides of pyridinyloxy substituted imidazo[2,1-b][1,3]thiazines

Q2 Chemistry

Current Chemistry Letters Pub Date : 2023-01-01 DOI:10.5267/j.ccl.2022.12.006

N. Slyvka, L. Saliyeva, S. Holota, M. Litvinchuk, S. Shishkina, M. Vovk

引用次数: 0

Abstract

Here derivatives of imidazo[2,1-b][1,3]thiazines are attractive objects for organic and medicinal chemists. In the present work chemoselective conditions for oxidation of the sulfur atom in the 6-(2-pyridinyloxy)substituted (benzo)imidazo[2,1-b][1,3]thiazines to the corresponding sulfoxides were proposed and their synthesis was performed. Synthesized sulfoxides exist in the diastereomeric mixture and individual diastereomers 2a-e and 3a-e were obtained using a chromatographic technique. The structure of compounds 2a-e and 3a-e were characterized using 1H, 13C NMR, LC-MS spectra, and X-ray analysis for derivative 2b. The anti-inflammatory activity screening in vivo was performed using the carrageenan model of inflammatory paw edema in white rats for all the diastereomeric mixtures and individual diastereomers. Diastereomer 2c possessed an anti-inflammatory effect with an inflammation inhibition index of 46.1% which was equal to the activity of the reference drug diclofenac sodium.

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吡啶基氧基取代咪唑[2,1-b][1,3]噻唑s -氧化物的合成及抗炎活性

在这里咪唑[2,1-b][1,3]噻嗪的衍生物是有机化学家和药物化学家关注的对象。本文提出了6-(2-吡啶基氧基)取代(苯并)咪唑[2,1-b][1,3]噻嗪中硫原子氧化为相应亚砜的化学选择条件，并进行了合成。合成的亚砜存在于非对映体混合物中，用色谱技术得到了单独的非对映体2a-e和3a-e。化合物2a-e和3a-e的结构通过1H、13C NMR、LC-MS和x射线分析对其衍生物2b进行了表征。采用角叉菜胶模型对所有非对映体混合物和单个非对映体进行体内抗炎活性筛选。非对映体2c具有抗炎作用，其炎症抑制指数为46.1%，与对照药双氯芬酸钠的活性相当。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Current Chemistry Letters Chemistry-Chemistry (all)

CiteScore

4.90

自引率

0.00%

发文量

审稿时长

20 weeks

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