Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis.
The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of alpha-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 microM, IC(50)=1.2 microM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 microM, IC(50)=0.76 microM) exhibited potent inhibitory effect against alpha-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.
Thanigaimalai
P
P
College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea.
Lee
Ki-Cheul
KC
Bang
Seong-Cheol
SC
Lee
Jee-Hyun
JH
Yun
Cheong-Yong
CY
Roh
Eunmiri
E
Hwang
Bang-Yeon
BY
Kim
Youngsoo
Y
Jung
Sang-Hun
SH
D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008543:Melanins / Q000378:metabolism*; D008544:Melanocytes / Q000187:drug effects / Q000378:metabolism; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D011743:Pyrimidines / Q000737:chemistry* / Q000494:pharmacology*; D013871:Thiones / Q000737:chemistry* / Q000494:pharmacology*; D000521:alpha-MSH / Q000037:antagonists & inhibitors* / Q000378:metabolism*
D008543:Melanins; D011743:Pyrimidines; D013871:Thiones; D000521:alpha-MSH; D014442:Monophenol Monooxygenase