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. Author manuscript; available in PMC: 2010 May 27.
Published in final edited form as: J Med Chem. 2009 May 28;52(10):3191–3204. doi: 10.1021/jm800861c

Figure 3.

Figure 3

Pharmacophores that contribute cytotoxicity and selectivity a). The pharmacophore features required for cytotoxicity, indicated by the activity of compounds tested against the parental KB-3-1 cell line. Pink sphere = A, H-bond acceptor, with the sphere located at the projected point of a hydrogen bond donor. Green sphere = H, hydrophobic group. Ring = aromatic ring. Blue sphere = X, thiosemicarbazone functional group. The pharmacophore sites are underlaid with the structure of 10 to aid in relating the pharmacophore features to structural features of the active compounds. b). The pharmacophore features required for selectivity against the P-gp expressing KB-V1 cell line: AH1H2H3R1R2X. Pink sphere = A, H-bond acceptor, with the sphere located at the projected point of a hydrogen bond donor. Green sphere = H, hydrophobic group. Ring = aromatic ring. Blue sphere = X, thiosemicarbazone functional group. Yellow sphere = Exclusion sphere. The pharmacophore sites are underlaid with the structure of 1 to aid in relating the pharmacophore features to structural features of the active compounds.