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Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.

Journal of the American Chemical Society (2008-09-06)
K C Nicolaou, Antonia F Stepan, Troy Lister, Ang Li, Ana Montero, G Scott Tria, Craig I Turner, Yefeng Tang, Jianhua Wang, Ross M Denton, David J Edmonds
ABSTRACT

The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of the platensimycin pharmacophore and establish certain structure-activity relationships from which the next generation of designed analogues of this new antibiotic may emerge.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Piperonal, 99%
Sigma-Aldrich
Piperonal, ≥99%, FCC, FG
Sigma-Aldrich
Piperonal, natural, 98%, FG