title: Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1H)-thiones for their anti-melanogenesis activity.
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.
authors.affiliation: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors.forename: Pillaiyar
authors.initials: P
authors.lastname: Thanigaimalai
authors.forename: Vinay K
authors.initials: VK
authors.lastname: Sharma
authors.forename: Ki-Cheul
authors.initials: KC
authors.lastname: Lee
authors.forename: Cheong-Yong
authors.initials: CY
authors.lastname: Yun
authors.forename: Youngsoo
authors.initials: Y
authors.lastname: Kim
authors.forename: Sang-Hun
authors.initials: SH
authors.lastname: Jung
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D008543:Melanins / Q000096:biosynthesis*; D051379:Mice; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D000521:alpha-MSH / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D008543:Melanins; D013871:Thiones; D000521:alpha-MSH