19734-66-8Relevant academic research and scientific papers
New N-n-propyl-substituted 3-aryl- and 3-cyclohexylpiperidines as partial agonists at the D4 dopamine receptor
Macchia, Marco,Cervetto, Luigi,Demontis, Gian Carlo,Longoni, Biancamaria,Minutolo, Filippo,Orlandini, Elisabetta,Ortore, Gabriella,Papi, Chiara,Sbrana, Andrea,Macchia, Bruno
, p. 161 - 168 (2003)
We have previously reported that compounds dimethyl-substituted on the phenyl ring of N-n-propyl-3-phenylpiperidines (PPEs) have a high (nM) affinity and selectivity toward the D4 dopamine receptor (D4 DAR) with m,p-dimethyl PPE (1) having the highest affinity and selectivity. In the present paper we have investigated the role of the methyl substitution by the synthesis of monomethylated (2a-c) and nonmethylated (2d) PPEs followed by the characterization of their biological properties using receptor binding assays. Our findings reveal that the methyl substitution of the phenyl ring is not necessary for a high and selective binding affinity to the D4 DAR. Moreover, we have also synthesized cyclohexylpiperidines (CHPEs, 3a-d), which all showed higher binding affinities for the D4 DAR than their aromatic counterparts. These results indicate that a π-π type interaction of the phenyl ring of PPEs with the D4 DAR might not be essential, whereas a simple hydrophobic attraction between the cyclohexyl substituent of CHPEs and a hypothesized lipophilic pocket of the receptor might be crucial. Furthermore, functional assays indicate that 3d, as well as 1, are partial agonist at the D4 DAR and therefore might represent new pharmacological tools to investigate the role of D4 DAR activation in the control of cognitive functions and emotional states in health and disease.
Approach to 3-(Cyclo)alkylpiperidines through 'sp3-sp3 via sp2-sp3' Coupling
Subota, Andrii I.,Grygorenko, Oleksandr O.,Valter, Yevheniia B.,Tairov, Maxim A.,Artamonov, Oleksiy S.,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.
supporting information, p. 408 - 411 (2015/02/19)
The idea of introducing (cyclo)alkyl substituents at the C-3 atom of the piperidine ring, that is, formal sp3-sp3 retrosynthetic disconnection, is implemented through a two-step reaction sequence including directed ortho metalation of a pyridine derivative and the subsequent quenching with a carbonyl compound, followed by catalytic hydrogenation. This robust but very efficient method allows for multigram preparation of sp3-rich 3-(cyclo)alkylpiperidines, which are valuable building blocks for medicinal chemistry and other areas.
PYRROLO[2,3-c]PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
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Page/Page column 12, (2010/10/20)
The present invention provides novel pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof, processes for the preparation thereof, and compositions comprising the same. The pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof of the present invention have excellent proton pump inhibition effects and possess the ability to attain a reversible proton pump inhibitory effect.
