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Pure Appl. Chem., 2009, Vol. 81, No. 6, pp. 1019-1026

Published online 2009-04-24

Structure-activity relationships of antitubercular scalaranes: Heteronemin revisited

Sunan Jaisamut1, Suriyan Thengyai1, Supreeya Yuenyongsawad1, Chatchanok Karalai2, Anuchit Plubrukarn3,1* and Khanit Suwanborirux3

1 Marine Natural Products Research Unit, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
2 Department of Chemistry, Faculty of Science, Prince of Songkhla University, Hat-Yai, Songkhla 90112, Thailand
3 Center of Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Patumwan, Bangkok 10330, Thailand

Abstract: A series of heteronemin-related antitubercular scalaranes, both from natural products and from chemical derivatization, were subjected to structure-activity investigations. Based on the activity profile, three main regions; i.e., the substituted groups hovering over C-19/C-18 and furan moiety, the functionalities in the vicinity of C-16 and the right-hand side of ring D, and the substituted groups on C-12, were speculated as the areas influencing the antitubercular activity of the scalaranes. The results suggested the promising possibility for the further investigation towards the modes of actions and/or target sites of the compounds.