Planta Med 2012; 78 - CL23
DOI: 10.1055/s-0032-1320258

Derivatizations and QSAR of marine-derived antitubercular scalaranes

S Thengyai 1, S Hannongbua 2, A Plubrukarn 1
  • 1Marine Natural Products Research Units, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
  • 2Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, Thailand

A series of scalarane sesterterpenes were prepared using heteronemin as a primary starting material. QSARs for the antitubercular activity of a dataset of 22 natural and chemically derived scalaranes were assessed using 2D-QSAR and CoMFA approaches. The 2D-QSAR model suggested the importance of hydrophilic perimeters with hydrophobic cores, whereas the CoMFA approach led to the conclusion that a non-steric, positive electrostatic induction over C12, and the lengthy, negative electrostatic extensions similar to an acetoxy group from C-16 of the scalarane skeleton may positively influence the potency.