Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells

To define the structural requirement of phenylthiourea, a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbaz...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2010-05, Vol.20 (9), p.2991-2993
Main Authors: Thanigaimalai, P., Le Hoang, Tuan Anh, Lee, Ki-Cheul, Bang, Seong-Cheol, Sharma, Vinay K., Yun, Cheong-Yong, Roh, Eunmiri, Hwang, Bang-Yeon, Kim, Youngsoo, Jung, Sang-Hun
Format: Article
Language:English
Subjects:
Animals
Benzaldehydes - chemistry
Biological and medical sciences
Medical sciences
Melanogenesis inhibitor
Melanoma, Experimental - drug therapy
Mice
Monophenol Monooxygenase - antagonists & inhibitors
Monophenol Monooxygenase - metabolism
Peptides - chemical synthesis
Peptides - chemistry
Peptides - therapeutic use
Pharmacology. Drug treatments
Phenylthiourea - chemical synthesis
Phenylthiourea - chemistry
Phenylthiourea - therapeutic use
Phenylthiourea and benzaldehyde thiosemicarbazone
Skin, nail, hair, dermoskeleton
Structure-Activity Relationship
Thiosemicarbazones - chemical synthesis
Thiosemicarbazones - chemistry
Thiosemicarbazones - therapeutic use
Tyrosinase inhibitor
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Summary:To define the structural requirement of phenylthiourea, a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 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 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2010.02.067