Structure-activity relationships of 6-nitroquinazolines: dual-acting compounds with inhibitory activities toward both TNF-alpha production and T cell proliferation

Chem Pharm Bull (Tokyo). 2002 Aug;50(8):1073-80. doi: 10.1248/cpb.50.1073.

Abstract

We synthesized various 6-nitroquinazolines by modifying the structure of compound 1 and evaluated their inhibitory activities toward both TNF-alpha production and T cell proliferation responses. The presence of the unsubstituted piperazine ring at the C(7)-position was required for both inhibitory activities. In this series of compounds, 5d and 5f, containing the 4-fluorophenyl and 3,4-difluorophenyl moiety, respectively, at the C(4)-position, showed the suppressing effects toward both responses with low cell growth inhibition. Furthermore, the oral administration of these compounds mentioned above at doses of 30 and 100 mg/kg also resulted in significant inhibition of TNF-alpha production induced by LPS in vivo.

MeSH terms

  • Animals
  • Drug Evaluation, Preclinical
  • Growth Inhibitors / chemistry*
  • Growth Inhibitors / pharmacology*
  • Lymphocyte Activation / drug effects
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Nitroquinolines / chemistry*
  • Nitroquinolines / pharmacology*
  • Quinazolines / chemistry*
  • Quinazolines / pharmacology*
  • Structure-Activity Relationship
  • T-Lymphocytes / cytology
  • T-Lymphocytes / drug effects*
  • T-Lymphocytes / metabolism
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Growth Inhibitors
  • Nitroquinolines
  • Quinazolines
  • Tumor Necrosis Factor-alpha