Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity

  • Bioorg Med Chem Lett. 2010 Aug 15;20(16):4771-3. doi: 10.1016/j.bmcl.2010.06.123.
Pillaiyar Thanigaimalai  1 ,  Vinay K Sharma ,  Ki-Cheul Lee ,  Cheong-Yong Yun ,  Youngsoo Kim ,  Sang-Hun Jung
Affiliations
  • 1. College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea.
PMID: 20638280 DOI: 10.1016/j.bmcl.2010.06.123
Abstract

In order to define the structural requirements of quinazoline-2(1H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1H)-thiones (3a-h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of alpha-MSH. The anti-melanogenesis activity of 3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione.