Novel benzo[d]imidazole-2(3H)-thiones as potent inhibitors of the alpha-melanocyte stimulating hormone induced melanogenesis in melanoma B16 cells.
In order to determine the optimum size of heterocycle of lead compound 1 (6-methyl-3-phenethyl-3,4-dihydro-1H-quinoline-2-thione; IC(50)=0.8 microM) for inhibition of melanogenesis, we have synthesized and evaluated some benzimdazole-2(3H)-thiones 5a-e. The preliminary bioassay has shown that the benzimdazole-2(3H)-thione motif of 5 is essential structural unit for their inhibitory activity. Among all thiones 5a-e, the compound 5d strongly inhibited the formation of melanin with IC(50) value of 1.3 microM.
Lee
Jee-Hyun
JH
College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon, Korea.
Thanigaimalai
Pillaiyar
P
Lee
Ki-Cheul
KC
Bang
Seong-Cheol
SC
Kim
Min-Seok
MS
Sharma
Vinay Kumar
VK
Yun
Cheong-Yong
CY
Roh
Eunmiri
E
Kim
Youngsoo
Y
Jung
Sang-Hun
SH
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D002460:Cell Line; D000242:Cyclic AMP / Q000378:metabolism; D006801:Humans; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D000521:alpha-MSH / Q000037:antagonists & inhibitors* / Q000378:metabolism
D000970:Antineoplastic Agents; D001562:Benzimidazoles; D008543:Melanins; D013871:Thiones; D000521:alpha-MSH; D000242:Cyclic AMP