1. Academic Validation
  2. Ketonethiosemicarbazones: structure-activity relationships for their melanogenesis inhibition

Ketonethiosemicarbazones: structure-activity relationships for their melanogenesis inhibition

  • Bioorg Med Chem Lett. 2011 Jun 15;21(12):3527-30. doi: 10.1016/j.bmcl.2011.04.146.
Pillaiyar Thanigaimalai 1 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, Republic of Korea.
Abstract

A series of 2-(1-phenylalkylidene)hydrazinecarbothioamides 2, 2-(1-phenylalkyl)hydrazinecarbothioamides 3, 2-(3,4-dihydronaphthalen-1(2H)-ylidene)hydrazinecarbothioamide (4), and 2-(1-(thiophen-2-yl)ethylidene)hydrazinecarbothioamide (5) were synthesized for their melanogenesis inhibition in melanoma B16 cells. The SAR of these ketonethiosemicarbazones revealed that the benzylidene hydrogen in aldehydethiosemicarbazones 1 can be replaced by hydrophobic moiety and substitutions with alkyl group for the terminal amino hydrogen of ketonethiosemicarbazones improved the activity appreciably. In addition, the double bond in thiosemicarbazones is an important factor for the increment of hydrophobicity. Thus hydrophobic ketonethiosemicarbazones are excellent inhibitors of melanogenesis like aldehydethiosemicarbazones.

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