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

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.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Balti M,Plas A,Meinguet C,Haufroid M,Thémans Q,Efrit ML,Wouters J,Lanners S

doi

10.1016/j.bmcl.2016.06.052

subject

Has Abstract

pub_date

2017-08-01 00:00:00

pages

3607-3610

issue

15

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(16)30663-1

journal_volume

27

pub_type

杂志文章

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