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

Affiliation

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.

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