Inhibitory effect of novel tetrahydropyrimidine-2(1 H)-thiones on melanogenesis

The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1 H)-thione 3e (>100% inhibition at 10 μM, IC 50 = 1.2 μM)...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2010-02, Vol.18 (3), p.1135-1142
Hauptverfasser:	Thanigaimalai, P., Lee, Ki-Cheul, Bang, Seong-Cheol, Lee, Jee-Hyun, Yun, Cheong-Yong, Roh, Eunmiri, Hwang, Bang-Yeon, Kim, Youngsoo, Jung, Sang-Hun
Format:	Artikel
Sprache:	eng
Schlagworte:	alpha-MSH - antagonists & inhibitors alpha-MSH - metabolism Biological and medical sciences Cell Line, Tumor Humans Hypopimenting Inhibitory Concentration 50 Medical sciences Melanins - metabolism Melanocytes - drug effects Melanocytes - metabolism Melanogenesis Monophenol Monooxygenase - antagonists & inhibitors Monophenol Monooxygenase - metabolism Pharmacology. Drug treatments Pyrimidines - chemistry Pyrimidines - pharmacology Skin, nail, hair, dermoskeleton Tetrahydropyrimidine-2(1 H)-thione Thiones - chemistry Thiones - pharmacology α-MSH-induced melanin production
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Zusammenfassung:	The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1 H)-thione 3e (>100% inhibition at 10 μM, IC 50 = 1.2 μM) and 1-(4- tert-butylbenzyl)-tetrahydropyrimidine-2(1 H)-thione 3f (>100% inhibition at 10 μM, IC 50 = 0.76 μM) exhibited potent inhibitory effect against α-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2009.12.044