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Synthesis and Evaluation of 1-(1-(Benzo[b]thiophen-2-yl)cyclohexyl)piperidine (BTCP) Analogues as Inhibitors of Trypanothione Reductase

✍ Scribed by Stephen Patterson; Deuan C. Jones; Emma J. Shanks; Julie A. Frearson; Ian H. Gilbert; Paul G. Wyatt; Alan H. Fairlamb

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 403 KB
Volume: 4
Category: Article
ISSN: 1860-7179
DOI: 10.1002/cmdc.200900098

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✦ Synopsis

Abstract

Thirty two analogues of phencyclidine were synthesised and tested as inhibitors of trypanothione reductase (TryR), a potential drug target in trypanosome and leishmania parasites. The lead compound BTCP (1, 1‐(1‐benzo[b]thiophen‐2‐yl‐cyclohexyl) piperidine) was found to be a competitive inhibitor of the enzyme (K~i~=1 μM) and biologically active against bloodstream T. brucei (EC~50~=10 μM), but with poor selectivity against mammalian MRC5 cells (EC~50~=29 μM). Analogues with improved enzymatic and biological activity were obtained. The structure–activity relationships of this novel series are discussed.

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