Abstract
We synthesized new N-phenylethyl-1H-indole-2-carboxamides as the first SAR study of allosteric modulators of the CB(1) receptor. The presence of the carboxamide functionality was required in order to obtain a stimulatory effect. The maximum stimulatory activity on CB(1) was exerted by carboxamides 13 (EC(50) = 50 nM) and 21 (EC(50) = 90 nM) bearing a dimethylamino or piperidinyl group, respectively, at position 4 of the phenethyl moiety and a chlorine atom at position 5 of the indole.
MeSH terms
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Allosteric Regulation
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Amides / chemical synthesis*
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Amides / chemistry
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Amides / pharmacology
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Cell Membrane / metabolism
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Humans
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / pharmacology
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Piperazines / chemical synthesis
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Piperazines / chemistry
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Piperazines / pharmacology
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Piperidines / chemical synthesis
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Piperidines / chemistry
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Piperidines / pharmacology
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Pyrrolidines / chemical synthesis
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Pyrrolidines / chemistry
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Pyrrolidines / pharmacology
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Radioligand Assay
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Receptor, Cannabinoid, CB1 / metabolism*
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Recombinant Proteins / metabolism
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Structure-Activity Relationship
Substances
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Amides
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Indoles
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Piperazines
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Piperidines
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Pyrrolidines
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Receptor, Cannabinoid, CB1
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Recombinant Proteins