Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

Pillaiyar Thanigaimalai, Eeda Venkateswara Rao, Ki Cheul Lee, Vinay K. Sharma, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

2-(Naphthalen-1-ylmethylene)hydrazinecarbothioamide (14, IC 50 = 1.1 μM) 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.

Original languageEnglish (US)
Pages (from-to)886-889
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number2
DOIs
StatePublished - Jan 15 2012

Bibliographical note

Funding Information:
This work was supported by a Priority Research Centers Program (2009-0093815) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology .

Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.

Keywords

  • 2-(Naphthalen-1-ylmethylene) hydrazinecarbothioamide
  • Melanogenesis inhibitor
  • Skin whitening agent
  • Thiosemicarbazone

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