A novel synthesis of benzo[c]phenanthridine skeleton and biological evaluation of isoquinoline derivatives

Chem Pharm Bull (Tokyo). 1999 Jun;47(6):900-2. doi: 10.1248/cpb.47.900.

Abstract

Benzo[c]phenanthridine skeleton was synthesized from easily available starting N-methyl-o-toluamide 2 and o-methylbenzonitrile 5 in 7 steps. Radical cyclization of styrene 10 afforded 6,11-dimethyl-6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one 13. Most 3-arylisoquinolines have displayed strong activities against human tumor cell lines. Especially, indenoisoquinolinone 13 exhibited excellent cytotoxicity (IC50 = 0.002 microgram/ml; HCT 15).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / pharmacology
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Isoquinolines
  • Phenanthridines