Synthesis, σ₁, σ₂-receptors binding affinity and antiproliferative action of new C1-substituted adamantanes

  • Bioorg Med Chem. 2012 May 15;20(10):3323-31. doi: 10.1016/j.bmc.2012.03.038.
Stefanos Riganas  1 ,  Ioannis Papanastasiou ,  George B Foscolos ,  Andrew Tsotinis ,  Jean-Jacques Bourguignon ,  Guillaume Serin ,  Jean-François Mirjolet ,  Kostas Dimas ,  Vassilios N Kourafalos ,  Andreas Eleutheriades ,  Vassilios I Moutsos ,  Humaira Khan ,  Stavroula Georgakopoulou ,  Angeliki Zaniou ,  Margarita Prassa ,  Maria Theodoropoulou ,  Stavroula Pondiki ,  Alexandre Vamvakides
Affiliations
  • 1. Faculty of Pharmacy, Department of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimioupoli-Zografou, 157 71 Athens, Greece.
PMID: 22512908 DOI: 10.1016/j.bmc.2012.03.038
Abstract

The synthesis of N-{4-[a-(1-adamantyl)benzyl]phenyl}piperazines 2a-e is described. The in vitro antiproliferative activity of most compounds against main Cancer cell lines is significant. The σ(1), σ(2)-receptors and sodium channels binding affinity of compounds 2 were investigated. One of the most active analogs, 2a, had an interesting in vivo Anticancer profile against the BxPC-3 and Mia-Paca-2 pancreas Cancer cell lines with Caspase-3 activation, which was associated with an anagelsic activity against the neuropathic pain.