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

Academic Article
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Overview

related to degree

  • Tria, G. Scott, Ph.D. in Organic Chemistry, Scripps Research 2005 - 2010
  • Wang, Jianhua Joseph, Ph.D. in Chemistry, Scripps Research 2005 - 2010
  • Li, Ang, Ph.D. in Chemistry, Scripps Research 2004 - 2009

authors

  • Nicolaou, K.C.
  • Stepan, A. F.
  • Lister, T.
  • Li, Ang
  • Montero, A.
  • Tria, G. Scott
  • Turner, C. I.
  • Tang, Y. F.
  • Wang, Jianhua Joseph
  • Denton, R. M.
  • Edmonds, D. J.

publication date

  • 2008

journal

  • Journal of the American Chemical Society  Journal

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.

subject areas

  • Adamantane
  • Aminobenzoates
  • Anilides
  • Aniline Compounds
  • Anti-Infective Agents
  • Benzaldehydes
  • Benzoates
  • Benzodioxoles
  • Cyclohexenes
  • Drug Design
  • Epoxy Compounds
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Pyrans
  • Staphylococcus aureus
  • Structure-Activity Relationship
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Identity

PubMed Central ID

  • PMC2669665

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja8044376

PubMed ID

  • 18771264
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Additional Document Info

start page

  • 13110

end page

  • 13119

volume

  • 130

issue

  • 39

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