Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

Bioorg Med Chem Lett. 2010 May 1;20(9):2991-3. doi: 10.1016/j.bmcl.2010.02.067. Epub 2010 Feb 20.

Abstract

In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC(50) value of 2.7 microM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of pi-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzaldehydes / chemistry*
  • Melanoma, Experimental / drug therapy*
  • Mice
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monophenol Monooxygenase / metabolism
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • Peptides / therapeutic use
  • Phenylthiourea / chemical synthesis
  • Phenylthiourea / chemistry*
  • Phenylthiourea / therapeutic use
  • Structure-Activity Relationship
  • Thiosemicarbazones / chemical synthesis
  • Thiosemicarbazones / chemistry*
  • Thiosemicarbazones / therapeutic use

Substances

  • 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide
  • Benzaldehydes
  • Peptides
  • Thiosemicarbazones
  • Phenylthiourea
  • Monophenol Monooxygenase
  • benzaldehyde