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Probing the structural requirements for antitubercular activity of scalarane derivatives using 2D-QSAR and CoMFA approaches

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Abstract

By use of 2D-QSAR and CoMFA approaches, a series of scalarane derivatives were assessed for which structural features confer antitubercular activity. The major contributions deduced from the 2D-QSAR models suggested positive effects on antitubercular activity of the shadow area on the XZ plane (representing the steric descriptor), the dipole moment, and relative positive charge (both representing the electrostatic descriptor). The contour map from the CoMFA model indicated the requirement for oxygenated functionality surrounding the furan moiety, particularly the extension of the acetoxy group either on C-16 toward the β plane or on C-19 toward the α plane. On the other hand, the region crowning C-12 was considered a sterically and negative-electrostatically disfavored area. Therefore, extension of a bulky negative functional group toward this area would diminish the binding interaction. The 2D-QSAR results agreed well with those from the CoMFA model and suggested the structural features of polarizable functionality that would enhance the antitubercular activity of the compounds in this series.

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Acknowledgments

This work was financially supported by Prince of Songkla University Research Supporting Grant (PHA530056S). We thank the National Electronic and Computer Technology Center (NECTEC), and the National Nanotechnology Center (NANOTEC), Thailand, for access to Material Studio and SYBYL software, and the National Center of Excellent in Petroleum, Petrochemical Technology, and Advanced Materials for computing research facilities. S.T. thanks the Royal Golden Jubilee Ph.D. Program (5.G.PS/48/H.1) and the Thailand Research Fund (TRF) for his thesis-supporting grant. S.H. is grateful to TRF for her research grant (RTA5080005). MNP is cosponsored by Prince of Songkla University and Faculty of Pharmaceutical Sciences Research Funds, and BNPME is sponsored by Office of the Higher Education Commission.

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Authors and Affiliations

  1. Marine Natural Products Research Unit (MNP), Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla, 90112, Thailand

    Suriyan Thengyai & Anuchit Plubrukarn

  2. Department of Chemistry, Faculty of Science, Center of Nanotechnology, Kasetsart University, Bangkok, 10900, Thailand

    Phornphimol Maitarat & Supa Hannongbua

  3. Center of Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Patumwan, Bangkok, 10330, Thailand

    Khanit Suwanborirux & Anuchit Plubrukarn

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  1. Suriyan Thengyai
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  2. Phornphimol Maitarat
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  3. Supa Hannongbua
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  4. Khanit Suwanborirux
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  5. Anuchit Plubrukarn
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Correspondence to Anuchit Plubrukarn.

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Thengyai, S., Maitarat, P., Hannongbua, S. et al. Probing the structural requirements for antitubercular activity of scalarane derivatives using 2D-QSAR and CoMFA approaches. Monatsh Chem 141, 621–629 (2010). https://doi.org/10.1007/s00706-010-0301-9

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  • DOI: https://doi.org/10.1007/s00706-010-0301-9

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