Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells.
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.
Thanigaimalai
P
P
College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, South Korea.
Hoang
Tuan Anh Le
TA
Lee
Ki-Cheul
KC
Bang
Seong-Cheol
SC
Sharma
Vinay K
VK
Yun
Cheong-Yong
CY
Roh
Eunmiri
E
Hwang
Bang-Yeon
BY
Kim
Youngsoo
Y
Jung
Sang-Hun
SH
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
C551010:2-(4-tert-butylbenzylidene)hydrazinecarbothioamide; D001547:Benzaldehydes; D010455:Peptides; D013882:Thiosemicarbazones; D010670:Phenylthiourea; D014442:Monophenol Monooxygenase; C032175:benzaldehyde