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Issue 3, 2017
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(Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH)

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A series of phenyl 4-[(indol-1-yl)alkyl]piperidine carbamates was synthesized and tested for inhibition of the endocannabinoid degrading enzyme fatty acid amide hydrolase (FAAH) and for metabolic stability in rat liver S9 fractions and porcine blood plasma. Structure–activity relationship studies revealed that variation of the length of the alkyl spacer connecting the indole and the piperidine heterocycle, introduction of substituents into the indole ring, replacement of the piperidine by a piperazine scaffold as well as opening of the piperidine ring system affect activity significantly. The metabolic stability of this compound class proved to be significantly higher than that of corresponding phenyl N-(indol-1-ylalkyl)carbamates.

Graphical abstract: (Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH)

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The article was received on 08 Dec 2016, accepted on 23 Jan 2017 and first published on 30 Jan 2017

Article type: Research Article
DOI: 10.1039/C6MD00683C
Citation: Med. Chem. Commun., 2017,8, 616-620
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    (Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH)

    H. Dahlhaus, W. Hanekamp and M. Lehr, Med. Chem. Commun., 2017, 8, 616
    DOI: 10.1039/C6MD00683C

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