Ketonethiosemicarbazones: Structure-activity relationships for their melanogenesis inhibition

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

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)3527-3530
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number12
DOIs
StatePublished - Jun 15 2011

Keywords

  • Aldehydethiosemicarbazones
  • Ketonethiosemicarbazones
  • Melanogenesis inhibition
  • Melanoma B16

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