266674-64-0Relevant academic research and scientific papers
Biologically Active Compounds through Catalysis: Efficient Synthesis of N-(Heteroarylcarbonyl)-N′-(arylalkyl)piperazines
Kumar, Kamal,Michalik, Dirk,Castro, Ivette Garcia,Tillack, Annegret,Zapf, Alexander,Arlt, Michael,Heinrich, Timo,Boettcher, Henning,Beller, Matthias
, p. 746 - 757 (2007/10/03)
A practical route for the synthesis of new biologically active 5-HT 2A receptor antagonists has been developed. In only three catalytic steps, this class of central nervous system (CNS) active compounds can be synthesized efficiently with high diversity. As the initial step, an anti-Markovnikov addition of amines to styrenes provides an easy route to N-(arylalkyl)piperazines, which constitute the core structure of the active molecules. Here, base-catalyzed hydroamination reactions of styrenes with benzylated piperazine proceeded in high yield even at room temperature. After catalytic debenzylation, the free amines were successfully carbonylated with different aromatic and heteroaromatic halides and carbon monoxide to yield the desired compounds in good to excellent yields. The two key reactions, base-catalyzed hydroamination of styrenes and palladium-catalyzed aminocarbonylation of haloarenes/heterocycles, showed tolerance towards various functional groups, thereby demonstrating the potential to synthesize a wide variety of new derivatives of this promising class of pharmaceuticals.
Synthesis and structure-activity relationships of novel arylalkyl 4- benzyl piperazine derivatives as σ site selective ligands
Younes, Salome,Labssita, Youssef,Baziard-Mouysset, Genevieve,Payard, Marc,Rettori, Marie-Claire,Renard, Pierre,Pfeiffer, Bruno,Caignard, Daniel-Henri
, p. 107 - 121 (2007/10/03)
Continuing our previous work that established that some chromones substitued by an aryl alkyl piperazino alkyl side chain are potent and selective sigma ligands and could be interesting in the treatment of psychosis, we synthesized 60 new compounds, replacing the chromone moiety by various cyclic systems. Many derivatives bind to the sigma sites in the nanomolar range and are generally selective in comparison with 5HT(1A) and the D2 receptors. One of the most potent ligands of these series, 1-(2- naphthyl methyl)-4-benzyl piperazine 29, has been studied in various pharmacological tests. Although it doesn't have potential in the treatment of psychosis, the results we obtained confirm the data which indicates that such derivatives could be interesting in the treatment of inflammatory diseases. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
