Synthesis of Fatty Acid Amides of Catechol Metabolites that Exhibit Antiobesity Properties

• Published in: ChemMedChem Vol. 5; no. 10; pp. 1781 - 1787
• Main Authors: Almeida, Bruno, Joglar, Jesús, Luque Rojas, María Jesús, Decara, Juan Manuel, Bermúdez-Silva, Francisco Javier, Macias-González, Manuel, Fitó, Montserrat, Romero-Cuevas, Miguel, Farré, Magí, Covas, María Isabel, Rodríguez de Fonseca, Fernando, de la Torre, Rafael
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 04.10.2010; WILEY‐VCH Verlag
• Subjects: Amides - chemical synthesis; Amides - chemistry; Amides - pharmacology; Animals; Anti-Obesity Agents - chemical synthesis; Anti-Obesity Agents - chemistry; Anti-Obesity Agents - pharmacology; Catechols - chemistry; Catechols - metabolism; CB1; endocannabinoids; Fatty Acids - chemistry; Kinetics; Male; N-Methyl-3,4-methylenedioxyamphetamine - chemistry; N-Methyl-3,4-methylenedioxyamphetamine - metabolism; obesity; PPAR alpha - chemistry; PPAR alpha - metabolism; PPAR-α; Rats; Rats, Wistar; Receptor, Cannabinoid, CB1 - chemistry; Receptor, Cannabinoid, CB1 - metabolism; receptors
• ISSN: 1860-7179; 1860-7187
• DOI: 10.1002/cmdc.201000161

A series of fatty acid amides of 3,4‐methylenedioxymethamphetamine (MDMA) catechol metabolites were synthesized in order to evaluate their biological activities. Upon administration, all synthesized compounds resulted in negative modulation of food intake in rats. The most active compounds have affinity for the CB1 receptor and/or PPAR‐α; part of their biological activity may be caused by these double interactions. Curbing the appetite: Fatty acid amides of 3,4‐methylenedioxymethamphetamine catechol metabolites were synthesized, and their biological activities were evaluated. All the compounds caused rats to decrease their food intake. The most active compounds show affinity for the CB1 receptor and/or PPAR‐α, so part of their biological activity may be caused by these double interactions.