Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

Bioorg Med Chem. 2010 Feb;18(3):1135-42. doi: 10.1016/j.bmc.2009.12.044. Epub 2009 Dec 22.

Abstract

The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of alpha-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 microM, IC(50)=1.2 microM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 microM, IC(50)=0.76 microM) exhibited potent inhibitory effect against alpha-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Melanins / metabolism*
  • Melanocytes / drug effects
  • Melanocytes / metabolism
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monophenol Monooxygenase / metabolism
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology*
  • Thiones / chemistry*
  • Thiones / pharmacology*
  • alpha-MSH / antagonists & inhibitors*
  • alpha-MSH / metabolism*

Substances

  • Melanins
  • Pyrimidines
  • Thiones
  • alpha-MSH
  • Monophenol Monooxygenase