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Facile TMSOI catalysed stereoselective synthesis of 2-Methylene selanyl-4-chromanols and anti-cancer activity
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-07 , DOI: 10.1016/j.tet.2017.11.007
Debayan Sarkar , Sagarika Behera , Sarbani Ashe , Bismita Nayak , Saikat Kumar Seth

In the present study, a catalytic synthesis of 2-methylene selanyl-4-chromanols has been described. The manuscript highlights a facile Trimethylsulphoxonium iodide (TMSOI) catalysed intramolecular 6-exo-trig coupling reaction in metal-free environment. The reaction exhibits satisfactory yields in presence of multiple free -hydroxyl groups. A stereoselective generation of syn-3-hex-yne-1,5diols has been explored. The relative stereochemistry has been confirmed by single-crystal X-ray of crystalline-selanyl-chromanols. To determine the anticancer efficacy of the synthesized compounds, cell viability assay using MTT was performed against MCF-7 breast cancer cell line. Notably, Compound 9j (IC50 = 3.157 μmol) was found to exhibit potent cytotoxic activity. Compounds 9a and 9e also showed activity with IC50 values of 31.60 ± 4.012 and 36.797 ± 2.72 μmol respectively highlighting the potential of the synthesized compounds as novel lead molecules for future development of potent anti-cancer therapeutics.



中文翻译:

简便的TMSOI催化2-亚甲基Selanyl-4-chromanol的立体选择性合成及其抗癌活性

在本研究中,已经描述了2-亚甲基硒基-4-色醇的催化合成。该手稿着重介绍了在无金属环境中,三碘碘化亚砜(TMSOI)催化的分子内6-exo-trig偶联反应的简便方法。在存在多个游离羟基的情况下,反应显示令人满意的产率。已经研究了立体选择性生成-3-己基-yne-1,5二醇。相对的立体化学已经通过结晶的硒基苯并二氢吡喃酚的单晶X射线证实。为了确定合成化合物的抗癌功效,使用MTT对MCF-7乳腺癌细胞系进行了细胞活力测定。值得注意的是,化合物9j(IC 50 =3.157μmol)表现出有效的细胞毒性活性。化合物9a9e也显示出活性,IC 50值分别为31.60±4.012和36.797±2.72μmol,凸显了合成化合物作为新型先导分子在潜在抗癌治疗药物未来发展中的潜力。

更新日期:2017-11-07
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