1. Academic Validation
  2. Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

Structure-activity relationship of naphthaldehydethiosemicarbazones in melanogenesis inhibition

  • Bioorg Med Chem Lett. 2012 Jan 15;22(2):886-9. doi: 10.1016/j.bmcl.2011.12.035.
Pillaiyar Thanigaimalai 1 Eeda Venkateswara Rao Ki-Cheul Lee Vinay K Sharma Eunmiri Roh Youngsoo Kim Sang-Hun Jung
Affiliations

Affiliation

  • 1 College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 305-764, Republic of Korea.
Abstract

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.

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