Syntheses and studies of amamistatin B analogs reveals that anticancer activity is relatively independent of stereochemistry, ester or amide linkage and select replacement of one of the metal chelating groups

Bioorg Med Chem Lett. 2011 May 1;21(9):2611-5. doi: 10.1016/j.bmcl.2011.01.084. Epub 2011 Jan 22.

Abstract

A series of analogs of the amamistatin natural products was designed and synthesized to facilitate additional anticancer structure-activity relationships. The results indicate that the anticancer activity is relatively independent of stereochemistry, ester or amide linkage and replacement of the oxazoline/oxazole based iron-binding group with a catechol.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / pharmacology
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Catechols / chemistry
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chelating Agents / chemical synthesis
  • Chelating Agents / chemistry*
  • Chelating Agents / pharmacology
  • Esters / chemical synthesis
  • Esters / chemistry
  • Esters / pharmacology
  • Female
  • Humans
  • Iron / chemistry
  • Metals / chemistry
  • Oligopeptides* / chemical synthesis
  • Oligopeptides* / chemistry
  • Oligopeptides* / pharmacology
  • Oxazoles* / chemical synthesis
  • Oxazoles* / chemistry
  • Oxazoles* / pharmacology
  • Structure-Activity Relationship

Substances

  • Amides
  • Antineoplastic Agents
  • Catechols
  • Chelating Agents
  • Esters
  • Metals
  • Oligopeptides
  • Oxazoles
  • amamistatin B
  • Iron
  • catechol