Effect of C2/C3-endo unsaturation on the cytotoxicity and DNA-binding reactivity of pyrrolo[2,1-c][1,4]benzodiazepines

Bioorg Med Chem Lett. 2000 Aug 21;10(16):1849-51. doi: 10.1016/s0960-894x(00)00350-4.

Abstract

A series of novel C2,C3-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) has been synthesised via cleavage of the N10-Alloc protecting group from appropriate precursors. Biophysical and biological evaluations show that the presence of C2/C3-endo unsaturation in the PBD C-ring enhances both DNA-binding reactivity and in vitro cytotoxic potency.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthramycin / chemistry
  • Antibiotics, Antineoplastic / chemistry*
  • Antibiotics, Antineoplastic / metabolism
  • Benzodiazepines / chemistry*
  • Benzodiazepines / metabolism
  • Chemistry, Organic
  • DNA / metabolism*
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Molecular Structure
  • Organic Chemistry Phenomena
  • Ovarian Neoplasms
  • Pyrroles / chemistry*
  • Pyrroles / metabolism
  • Tumor Cells, Cultured

Substances

  • Antibiotics, Antineoplastic
  • Pyrroles
  • Anthramycin
  • Benzodiazepines
  • DNA