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Iodine-catalyzed three-component one-pot synthesis of novel 1,8-dioxo-decahydroacridines derivatives bearing benzene sulfonamide moiety

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Abstract

An efficient synthetic method for 1,8-dioxo-decahydroacridines derivatives bearing the biologically active sulfonamide moiety is described. Aromatic aldehyde reacted with 5,5-dimethyl-1,3-cyclohexanedione and sulfanilamide, with molecular iodine as catalyst, to give 1,8-dioxo-decahydroacridines derivatives in high to excellent yield. The structures of these compounds were established on the basis of elemental (C, H and N) and spectral analysis (1H NMR, 13C NMR, MS and FTIR). All the compounds were tested for their cytotoxic activity in vitro against three human tumor cell lines: human mammary cancer cells (MCF-7), human cervical carcinoma cells (Hela), and human lung cancer cells (A549) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Most of them showed moderate to potent cytotoxic activity against the tested cell lines. Among them, the most active compound 4e exhibited more efficient activity (10.92 μM) against MCF-7 cells than cisplatin (11.06 μM).

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Acknowledgments

We are grateful to the National Basic Research 973 Program (Grant No. 2010CB534913), Hebei Provincial Natural Science Foundation of China-Shijiazhuang Pharmaceutical Group (CSPC) Foundation (B2011201174), Hebei Province Nature Science Fund for Distinguished Young Scholars (B2011201164), the Nature Science Fund of Hebei Province (B2011201135), the Key Basic Research Special Foundation of Science Technology Ministry of Hebei Province (11966412D, 12966418D) and Open Fund of Key Laboratory of Chemical Biology of Hebei Province (No. 09265631D-7).

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Authors and Affiliations

  1. Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, 071002, People’s Republic of China

    Shenghui Li, Shan Ding, Shengjie Xu, Jinchao Zhang, Shuxiang Wang, Chuanqi Zhou & Xiaoliu Li

  2. Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Ministry of Education, Hebei University, Baoding, 071002, People’s Republic of China

    Shenghui Li, Shan Ding, Shengjie Xu, Jinchao Zhang, Shuxiang Wang, Chuanqi Zhou & Xiaoliu Li

  3. College of Chemistry & Environmental Science, Hebei University, Baoding, 071002, People’s Republic of China

    Shenghui Li, Shan Ding, Shengjie Xu, Jinchao Zhang, Shuxiang Wang, Chuanqi Zhou & Xiaoliu Li

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  1. Shenghui Li
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  2. Shan Ding
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  3. Shengjie Xu
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  4. Jinchao Zhang
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  5. Shuxiang Wang
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  7. Xiaoliu Li
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Correspondence to Shenghui Li or Jinchao Zhang.

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Li, S., Ding, S., Xu, S. et al. Iodine-catalyzed three-component one-pot synthesis of novel 1,8-dioxo-decahydroacridines derivatives bearing benzene sulfonamide moiety. Res Chem Intermed 40, 2091–2102 (2014). https://doi.org/10.1007/s11164-013-1105-4

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