2017
DOI: 10.1039/c6md00683c
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(Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH)

Abstract: Studies on FAAH inhibitory potency and metabolic stability of indolyl-substituted alkyl- and alkylpiperidine carbamates are described.

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Cited by 5 publications
(16 citation statements)
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“…For all other compounds, a much stronger degradation was observed. This was particularly pronounced for the pyridinyl-derivatives (44−48), the 3-and 2-fluoro- (27,28), the 3-cyano- (30), and the 4-carboxy-substituted (33) compounds. It was noticeable that the pyridines 45 and 46 bearing methyl groups at position 2 or 4 were somewhat more stable than the unsubstituted and the other methylated pyridines.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…For all other compounds, a much stronger degradation was observed. This was particularly pronounced for the pyridinyl-derivatives (44−48), the 3-and 2-fluoro- (27,28), the 3-cyano- (30), and the 4-carboxy-substituted (33) compounds. It was noticeable that the pyridines 45 and 46 bearing methyl groups at position 2 or 4 were somewhat more stable than the unsubstituted and the other methylated pyridines.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…We had also investigated corresponding compounds, such as 8 (Figure 1). 28 The latter had been shown to be a highly potent FAAH inhibitor that did not inhibit MAGL. Finally, we were interested in whether MAGL inhibition could also be achieved by introducing a carboxy group to the phenyl ring of the phenyl piperidine-1-carboxylate 8, particularly in the orthoposition.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…The synthesis of the 6-fluoroindole-substituted target compounds with alkyl spacer between carbamate group and indole heterocycle (9,11,13,15) were obtained by reaction of the appropriate indolyl-substituted alkan-1-amines (8, 10, 12, 14) [23,24] with an activated carbonate formed from 1,1,1,3,3,3hexafluoropropan-2-ol and bis(pentafluorophenyl) carbonate in acetonitrile in presence of triethylamine (Scheme 1). [18] For the synthesis of the indol-1-ylalkyl-substituted piperidine carbamates 20, 24, 28 and 32, 6-fluoroindole was Nalkylated with the corresponding 4-(mesyloxyalkyl)piperidine protected as its benzyloxycarbonyl derivative (17, 21, 25, 29) [25] using sodium hydride as base (Scheme 2).…”
Section: Chemical Synthesismentioning
confidence: 99%
“…[18] For the synthesis of the indol-1-ylalkyl-substituted piperidine carbamates 20, 24, 28 and 32, 6-fluoroindole was Nalkylated with the corresponding 4-(mesyloxyalkyl)piperidine protected as its benzyloxycarbonyl derivative (17, 21, 25, 29) [25] using sodium hydride as base (Scheme 2). The protecting group of the formed intermediates 18, 22, 26 and 30 was removed by catalytic hydrogenation and the resulting free secondary amine (19,23,27,31) acylated with an activated 1,1,1,3,3,3-hexafluoropropyl carbonate as described above to obtain the desired carbamates.…”
Section: Chemical Synthesismentioning
confidence: 99%