Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis

Ki Cheul Lee, Pillaiyar Thanigaimalai, Vinay K. Sharma, Min Seok Kim, Eunmiri Roh, Bang Yeon Hwang, Youngsoo Kim, Sang Hun Jung

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene)hydrazinecarbothioamide (2q, >100% inhibition at 10 μM, IC50 = 1.1 μM, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity.

Original languageEnglish (US)
Pages (from-to)6794-6796
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number22
DOIs
StatePublished - Nov 15 2010

Bibliographical note

Funding Information:
This work was supported by a grant ( R01-2007-000-20099-0 ) and 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 2011 Elsevier B.V., All rights reserved.

Keywords

  • Hydrophobicity
  • Melanogenesis inhibitor
  • Thiosemicarbazones

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