title: Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells.
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.
authors.affiliation: College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, South Korea.
authors.forename: P
authors.initials: P
authors.lastname: Thanigaimalai
authors.forename: Tuan Anh Le
authors.initials: TA
authors.lastname: Hoang
authors.forename: Ki-Cheul
authors.initials: KC
authors.lastname: Lee
authors.forename: Seong-Cheol
authors.initials: SC
authors.lastname: Bang
authors.forename: Vinay K
authors.initials: VK
authors.lastname: Sharma
authors.forename: Cheong-Yong
authors.initials: CY
authors.lastname: Yun
authors.forename: Eunmiri
authors.initials: E
authors.lastname: Roh
authors.forename: Bang-Yeon
authors.initials: BY
authors.lastname: Hwang
authors.forename: Youngsoo
authors.initials: Y
authors.lastname: Kim
authors.forename: Sang-Hun
authors.initials: SH
authors.lastname: Jung
mesh_terms: D000818:Animals; D001547:Benzaldehydes / Q000737:chemistry*; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D010670:Phenylthiourea / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use
chemical_list: C551010:2-(4-tert-butylbenzylidene)hydrazinecarbothioamide; D001547:Benzaldehydes; D010455:Peptides; D013882:Thiosemicarbazones; D010670:Phenylthiourea; D014442:Monophenol Monooxygenase; C032175:benzaldehyde