Synthesis and cytotoxicity evaluation of 6,11-dihydro-pyridazo- and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-diones

Bioorg Med Chem. 2004 Apr 1;12(7):1623-8. doi: 10.1016/j.bmc.2004.01.029.

Abstract

The 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione derivatives were synthesized from 6,7-dichloro-5,8-phthalazinedione and 6,7-dichloro-5,8-quinolinedione, respectively, producing a series of new anticancer drugs. The cytotoxic activities of the prepared compounds were evaluated by a SRB (Sulforhodamine B) assay against the following tumor cell lines: A459 (human lung), SK-OV-3 (human ovarian), SK-MEL-2 (human melanoma), XF498 (human CNS), and HCT 15 (human colon). Almost all the derivatives of the 6,11-dihydro-pyridazo[2[,3-b]phenazine-6,11-dione and 6,11-dihydro-pyrido[2,3-b]phenazine-6,11-dione, tetracyclic heteroquinone analogues with four or three nitrogen atoms, exhibited excellent cytotoxicity on almost all the human tumor cell lines tested. Specifically, 6,11-dihydro-pyridazo[2,3-b]phenazine-6,11-dione (4a) exhibited potent activity against all the tumor cell lines, and in particular, its cytotoxic effect against HCT 15 (ED(50)=0.004 microg/mL) was 25 times greater than that of doxorubicin (ED(50)=0.093 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Phenazines / chemical synthesis*
  • Phenazines / pharmacology*
  • Phthalazines / chemical synthesis
  • Phthalazines / chemistry
  • Phthalazines / pharmacology
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Rhodamines / chemistry
  • Structure-Activity Relationship

Substances

  • 6,11-dihydro-pyridazo(2,3-b)phenazine-6,11-dione
  • 6,11-dihydro-pyrido(2,3-b)phenazine-6,11-dione
  • 6,7-dichloro-5,8-phthalazinedione
  • 6,7-dichloro-5,8-quinolinedione
  • Antineoplastic Agents
  • Phenazines
  • Phthalazines
  • Quinolines
  • Rhodamines
  • lissamine rhodamine B