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New macrocycles with potent antituberculosis activity accessed by one-pot multicomponent reactions

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Chemistry of Heterocyclic Compounds Aims and scope

Based on modeling studies, we hypothesized that tylosin derivatives without formyl group should rather adopt an erythromycin-like binding mode to the ribosome. Twenty four 16-membered macrocyclic compounds were accessed by multicomponent reactions (Gewald, Ugi) of tylosin and investigated for their antituberculosis activity. The best compound was twice as active as tylosin and might thus be a good starting point for further optimization of biological properties.

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Authors and Affiliations

  1. University of Pittsburgh, 10040 Biomedical Science Tower 3, 3501 Fifth Ave., Pittsburgh, PA, 15260, USA

    D. Kim, Y. Huang, K. Wang & A. Dömling

  2. University of Groningen, PO Box 72, 9700, AB Groningen, The Netherlands

    A. Dömling

Authors
  1. D. Kim
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  2. Y. Huang
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  3. K. Wang
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  4. A. Dömling
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Correspondence to A. Dömling.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 911–921, June, 2013.

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Kim, D., Huang, Y., Wang, K. et al. New macrocycles with potent antituberculosis activity accessed by one-pot multicomponent reactions. Chem Heterocycl Comp 49, 849–859 (2013). https://doi.org/10.1007/s10593-013-1319-9

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  • DOI: https://doi.org/10.1007/s10593-013-1319-9

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