Synthesis of antimicrobial natural products targeting FtsZ: (+/-)-dichamanetin and (+/-)-2' ''-hydroxy-5' '-benzylisouvarinol-B

Org Lett. 2005 Dec 8;7(25):5609-12. doi: 10.1021/ol052269z.

Abstract

[chemical structure: see text]. Two natural products have been synthesized using a ZnCl2-mediated benzylic coupling reaction. Both are potent inhibitors of the GTPase activity of FtsZ, a highly conserved protein that is essential for bacterial cytokinesis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacterial Proteins / drug effects*
  • Bacterial Proteins / physiology
  • Biological Products* / chemical synthesis
  • Biological Products* / chemistry
  • Biological Products* / pharmacology
  • Chlorides
  • Cytokinesis / physiology
  • Cytoskeletal Proteins / drug effects*
  • Cytoskeletal Proteins / physiology
  • Enzyme Inhibitors* / chemical synthesis
  • Enzyme Inhibitors* / chemistry
  • Enzyme Inhibitors* / pharmacology
  • Flavanones* / chemical synthesis
  • Flavanones* / chemistry
  • Flavanones* / pharmacology
  • GTP Phosphohydrolases / antagonists & inhibitors*
  • Stereoisomerism
  • Zinc Compounds

Substances

  • 2'''-hydroxy-5''-benzylisouvarinol-B
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Biological Products
  • Chlorides
  • Cytoskeletal Proteins
  • Enzyme Inhibitors
  • Flavanones
  • FtsZ protein, Bacteria
  • Zinc Compounds
  • dichamanetin
  • zinc chloride
  • GTP Phosphohydrolases