Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties

Silvia Serra, Laurence Moineaux, Christelle Vancraeynest, Bernard Masereel, Johan Wouters, Lionel Pochet, Raphaël Frédérick

Research output: Contribution to journalArticle

Abstract

With the aim to explore the interest of the thiosemicarbazide scaffold for the inhibition of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an IC50 of 1.2 μM. The SAR depicted showed that substitution in the 3- and 4-position relative to the phenylthiosemicarbazide are very promising whereas substitution in the 2-position always leads to less potent or inactive derivatives. In fact the study highlighted a novel interesting scaffold for IDO inhibition for further development.

Original languageEnglish
Pages (from-to)96-105
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume82
DOIs
Publication statusPublished - 23 Jul 2014

Keywords

  • IDO
  • Immunotherapy
  • Indoleamine 2,3-dioxygenase
  • Molecular modelling
  • Thiosemicarbazide

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