Privileged structure based ligands for melanocortin receptors—Substituted benzylic piperazine derivatives

…, PL Ornstein, CG Paredes, TP O'Brian…

Index: Fisher, Matthew J.; Backer, Ryan T.; Collado, Ivan; De Frutos, Oscar; Husain, Saba; Hsiung, Hansen M.; Kuklish, Steve L.; Mateo, Ana I.; Mullaney, Jeffrey T.; Ornstein, Paul L.; Paredes, Cristina Garcia; O'Brian, Thomas P.; Richardson, Timothy I.; Shah, Jikesh; Zgombick, John M.; Briner, Karin Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 22 p. 4973 - 4978

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Citation Number: 17

Abstract

Replacement of the aryl piperazine moiety in compound 1 with a variety of substituted benzylic piperazines (6) yields compounds that afford melanocortin receptor 4 (MCR4) activity. Analogs with ortho substitution on the aromatic ring afforded the highest affinity. Resolution of the stereocenter of the benzylic piperazine based privileged structure revealed that the R-enantiomer was more active.