1005765-07-0Relevant academic research and scientific papers
An improved synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT): A selective MT2 melatonin receptor antagonist
Lucarini, Simone,Bedini, Annalida,Spadoni, Gilberto,Piersanti, Giovanni
, p. 147 - 150 (2008)
A novel, efficient and diastereoselective procedure was developed for the gram-scale synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT), a selective MT2 melatonin receptor antagonist. The synthetic strategy involved the conversion of 4
Toward the definition of stereochemical requirements for MT 2-selective antagonists and partial agonists by studying 4-phenyl-2-propionamidotetralin derivatives
Bedini, Annalida,Lucarini, Simone,Spadoni, Gilberto,Tarzia, Giorgio,Scaglione, Francesco,Dugnani, Silvana,Pannacci, Marilou,Lucini, Valeria,Carmi, Caterina,Pala, Daniele,Rivara, Silvia,Mor, Marco
, p. 8362 - 8372 (2012/02/14)
New derivatives of 4-phenyl-2-propionamidotetralin (4-P-PDOT) were prepared and tested on cloned MT1 and MT2 receptors, with the purpose of merging previously reported pharmacophores for nonselective agonists and for MT2-selective antagonists. A 8-methoxy group increases binding affinity of both (±)-cis- and (±)-trans-4-P-PDOT, and it can be bioisosterically replaced by a bromine. Conformational analysis of 8-methoxy-4-P-PDOT by molecular dynamics, supported by NMR data, revealed an energetically favored conformation for the (2S,4S)-cis isomer and a less favorable conformation for the (2R,4S)-trans one, fulfilling the requirements of a pharmacophore model for nonselective melatonin receptor agonists. A new superposition model, including features characteristic of MT2- selective antagonists, suggests that MT1/MT2 agonists and MT2 antagonists can share the same arrangement for their pharmacophoric elements. The model correctly predicted the eutomers of (±)-cis- and (±)-trans-4-P-PDOT. The model was validated by preparing three dihydronaphthalene derivatives, either able or not able to reproduce the putative active conformation of 4-P-PDOT. (Figure presented)
Diastereo- and enantioselective hydrogenation of a challenging enamide derived from 4-phenyl-2-tetralone: An appealing shortcut towards enantiopure cis-2-aminotetraline derivatives
Lucarini, Simone,Alessi, Matteo,Bedini, Annalida,Giorgini, Giorgia,Piersanti, Giovanni,Spadoni, Gilberto
scheme or table, p. 550 - 554 (2010/08/13)
A clean, efficient, and diasteroselective (dr >95%) catalytic hydrogenation of the enamide N-(4- phenyl-3, 4-dihydronaphthalen-2-yl) propionamide (2a) using palladium on carbon is performed. This procedure provides the melatonin receptor ligand (±)-cis-4-
