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Application of 2,4-bis(halomethyl)quinoline: synthesis and biological activities of 2,4-bis(benzofuran-2-yl)- and 2,4-bis(aroxymethyl)quinolines

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Abstract

In the present investigation, the synthesis of a new type of halomethylquinoline building block, i.e., ethyl 4-(bromomethyl)-2-(chloromethyl)quinoline-3-carboxylate, and its synthetic applications in the reaction with salicylaldehydes or phenols to make a range of structurally novel and intriguing 2,4-bis(benzofuran-2-yl)quinoline- and 2,4-bis(aroxymethyl)quinoline-3-carboxylic acids is described. Our newly synthesized compounds belong to a new class of quinoline derivatives, and their structures were elucidated on the basis of their spectral data and elemental analyses. Screening for in vitro anti-tubercular against Mycobacterium smegmatis and anti-bacterial activities against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa was carried out. Compounds 5e and 5g showed significant anti-tubercular activity comparable with the reference rifampicin and might be used as promising candidates for further investigation.

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Acknowledgements

The authors would like to thank the Scientific Research Foundation of the National Natural Science Foundation of China (Grant Nos. 21476028 and 21402011) for financial support.

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Authors and Affiliations

  1. Institute of Superfine Chemicals, Bohai University, Keji Street, Jinzhou, 121000, People’s Republic of China

    Yang Li, Qiqi Xu, Zhiyuan Li & Wentao Gao

  2. School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang, 110016, People’s Republic of China

    Yu Chen

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  1. Yang Li
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Correspondence to Yang Li or Yu Chen.

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Li, Y., Xu, Q., Li, Z. et al. Application of 2,4-bis(halomethyl)quinoline: synthesis and biological activities of 2,4-bis(benzofuran-2-yl)- and 2,4-bis(aroxymethyl)quinolines. Mol Divers 24, 167–178 (2020). https://doi.org/10.1007/s11030-019-09938-3

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