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Synthesis and anticancer activity evaluation of benzo[6,7]oxepino[3,2-b] pyridine derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2020-08-16 , DOI: 10.1016/j.tet.2020.131473
Phanida Thongaram , Suparerk Borwornpinyo , Phongthon Kanjanasirirat , Kedchin Jearawuttanakul , Mesayamas Kongsema , Nutthawat Chuanopparat , Paiboon Ngernmeesri

A cascade reaction of 3-hydroxy-2-methylpyridine 1-oxide and substituted 2-fluorobenzal-dehydes involving nucleophilic aromatic substitution (SNAr) and Knoevenagel condensation has been developed. This reaction provided easy access to benzo[6,7]oxepino[3,2-b]pyridine 1-oxide derivatives in moderate to good yields. Subsequent reduction of these compounds provided their deoxygenated forms in good to excellent yields. Moreover, some of the synthesized compounds were found to be active against human colorectal cancer cells (HCT-116 cell lines) with IC50 values in the range of 24.95–45.80 μM.



中文翻译:

苯并[6,7]氧哌啶[3,2- b ]吡啶衍生物的合成及抗癌活性评估

3-羟基-2-甲基吡啶1-氧化物和取代的涉及亲核芳香取代(S 2- fluorobenzal-dehydes的级联反应Ñ Ar)和Knoevenagel缩合已经研制成功。该反应提供了以中等至良好收率的容易获得苯并[6,7]氧杂环庚烷[3,2 - b ]吡啶1-氧化物衍生物的途径。这些化合物的随后还原以良好至优异的产率提供了它们的脱氧形式。此外,发现一些合成的化合物对人结肠直肠癌细胞(HCT-116细胞系)具有活性,IC 50值在24.95–45.80μM范围内。

更新日期:2020-09-05
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