Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis

Pillaiyar Thanigaimalai, Ki Cheul Lee, Vinay Kumar Sharma, Niti Sharma, Eunmiri Roh, Youngsoo Kim, Sang Hun Jung

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC 50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.

Original languageEnglish (US)
Pages (from-to)1285-1288
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume59
Issue number10
DOIs
StatePublished - Oct 2011

Keywords

  • Benzimidazole-2-thione
  • Indole-2-thiol
  • Inoline-2-thione
  • Melanogenesis inhibitor

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