Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity

Molecules. 2015 Jul 1;20(7):12029-44. doi: 10.3390/molecules200712029.

Abstract

A series of novel 4-substituted-N-(phenylcarbamoyl)-3-pyridinesulfonamides 11-27 have been synthesized by the reaction of 4-substituted pyridine-3-sulfonamides 2-10 with the appropriate aryl isocyanates in presence of potassium carbonate. The in vitro anticancer activity of compounds 11, 12, 14-21 and 24-26 was evaluated at the U.S. National Cancer Institute and in light of the results, some structure-activity relationships were discussed. The most prominent compound, N-[(4-chlorophenyl)carbamoyl]-4-[4-(3,4-dichlorophenyl)piperazin-1-yl]pyridine-3-sulfonamide (21) has exhibited a good activity profile and selectivity toward the subpanels of leukemia, colon cancer and melanoma, with average GI50 values ranging from 13.6 to 14.9 µM.

Keywords: anticancer; antitumor activity; diarylsulfonylureas; pyridine-3-sulfonamides; sulfonamides; sulfonylureas.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Phenylurea Compounds / chemical synthesis*
  • Phenylurea Compounds / chemistry
  • Phenylurea Compounds / pharmacology*

Substances

  • Antineoplastic Agents
  • Phenylurea Compounds