Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: excellent substrates for NAD(P)H:quinone oxidoreductase 1

Bioorg Med Chem. 2013 Jun 1;21(11):2999-3009. doi: 10.1016/j.bmc.2013.03.071. Epub 2013 Apr 6.

Abstract

A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Cell Line, Tumor
  • Enzyme Assays
  • Humans
  • Indazoles / chemical synthesis*
  • Indazoles / chemistry
  • NAD(P)H Dehydrogenase (Quinone) / antagonists & inhibitors*
  • NAD(P)H Dehydrogenase (Quinone) / chemistry
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxidation-Reduction
  • Quinones / chemical synthesis
  • Quinones / chemistry*
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry

Substances

  • Antineoplastic Agents
  • Benzofurans
  • Indazoles
  • Oxazoles
  • Quinones
  • Thiophenes
  • NAD(P)H Dehydrogenase (Quinone)
  • NQO1 protein, human