1-(Benzenesulfonyl)-1,5-dihydro-4,1-benzoxazepine as a new scaffold for the design of antitumor compounds

Future Med Chem. 2017 Jul;9(11):1129-1140. doi: 10.4155/fmc-2017-0006. Epub 2017 Jul 19.

Abstract

Aim: Bozepinib is a potent and selective anticancer compound which chemical structure is made up of a benzofused seven-membered ring and a purine moiety. We previously demonstrated that the purine fragment does not exert antiproliferative effect per se.

Methodology: A series of 1-(benzenesulfonyl)-4,1-benzoxazepine derivatives were synthesized in order to study the influence of the benzofused seven-membered ring in the biological activity of bozepinib by means of antiproliferative, cell cycle and apoptosis studies.

Results & conclusion: Our results show that the methyleneoxy enamine sulfonyl function is essential in the antitumor activity of the structures and thus, it is a scaffold suitable for further modification with a view to obtain more potent antitumor compounds.

Keywords: antitumor; apoptosis; benzoxazepine; bozepinib; cell cycle; methyleneoxy enamine sulfonyl.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Apoptosis
  • Azepines / chemical synthesis*
  • Azepines / pharmacology
  • Benzenesulfonates / chemical synthesis*
  • Benzenesulfonates / pharmacology
  • Cell Cycle
  • Cell Line, Tumor
  • Cell Proliferation
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Azepines
  • Benzenesulfonates