Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase

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Abstract

Docking studies of 4-phenylthiazolinethione on human IDO1 suggest complexation of the heme iron by the exocyclic sulfur atom further reinforced by hydrophobic interactions of the phenyl ring within pocket A of the enzyme. On this basis, chemical modifications were proposed to increase inhibition activity. Synthetic routes had to be adapted and optimized to yield the desired substituted 4- and 5-arylthiazolinethiones. Their biological evaluation shows that 5-aryl regioisomers are systematically less potent than the corresponding 4-aryl analogs. Substitution on the phenyl ring does not significantly increase inhibition potency, except for 4-Br and 4-Cl derivatives.

Original languageEnglish
Pages (from-to)3607-3610
Number of pages4
JournalBioorganic and medicinal chemistry letters
Volume27
Issue number15
DOIs
Publication statusPublished - 1 Aug 2017

Keywords

  • 4-Phenyl thiazolinethione
  • Anti-cancer
  • Aryl-thiazoline thione
  • IDO inhibition
  • Indoleamine 2,3-dioxygenase (IDO)
  • Indoleamine-Pyrrole 2,3,-Dioxygenase/antagonists & inhibitors
  • Stereoisomerism
  • Humans
  • Thiones/chemical synthesis
  • Thiazolidines/chemical synthesis
  • Structure-Activity Relationship
  • Molecular Docking Simulation
  • Enzyme Inhibitors/chemical synthesis

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