Document Detail


Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition.
MedLine Citation:
PMID:  22217872     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC(50)=1.1μM) was discovered as a highly potent inhibitor of melanogenesis. To define the role of hydrogens (at N1 and N3) and sulfur in 14, a series of analogs 15a-p were synthesized and evaluated for anti-melanogenic activity using melanoma B16 cells under the stimulus of α-MSH. It was observed that replacement of either of these hydrogens at N1 or N3 by substituents increases the activity significantly. Conversely, concomitant substitutions decrease the inhibitory potency. In addition, the presence of sulfur in thiosemicarbazone is essential for the activity.
Authors:
Pillaiyar Thanigaimalai; Eeda Venkateswara Rao; Ki-Cheul Lee; Vinay K Sharma; Eunmiri Roh; Youngsoo Kim; Sang-Hun Jung
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-13
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  -     ISSN:  1464-3405     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2012-1-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Elsevier Ltd. All rights reserved.
Affiliation:
College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea.
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