Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships

J Med Chem. 1990 Sep;33(9):2393-407. doi: 10.1021/jm00171a013.

Abstract

A series of diarylsulfonylureas with exceptionally broad-spectrum activity against syngeneic rodent solid tumors in vivo is described. Their discovery resulted from a program dedicated to in vivo screening for novel oncolytics in solid tumor models, rather than traditional ascites leukemia models. The structures, oral efficacy, side-effect profile, and mechanism of action of these sulfonylureas appear to be distinct from previously known classes of oncolytics. An extensive series of analogues was prepared to probe structure-activity relationships (SAR), with particular focus on the substituent patterns of each aryl domain. Quantitative analysis of these substituent SARs, using the method of cluster significance analysis, showed the lipophilicity of the substituents to be the dominant determinant of activity. One compound from the series, LY186641 (104, sulofenur), has progressed to Phase I clinical trials as an antitumor drug.

MeSH terms

  • Adenocarcinoma / drug therapy
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / therapeutic use
  • Chemical Phenomena
  • Chemistry
  • Humans
  • Lymphoma, Non-Hodgkin / drug therapy
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Mice, Inbred C57BL
  • Mice, Inbred DBA
  • Multiple Myeloma / drug therapy
  • Rats
  • Rats, Inbred Strains
  • Structure-Activity Relationship
  • Sulfonylurea Compounds / chemical synthesis*
  • Sulfonylurea Compounds / therapeutic use
  • Tumor Cells, Cultured / drug effects

Substances

  • Antineoplastic Agents
  • Sulfonylurea Compounds
  • LY 181984
  • sulofenur