@article{3061488, title = "Synthesis, σ 1, σ 2-receptors binding affinity and antiproliferative action of new C1-substituted adamantanes", author = "Riganas, S. and Papanastasiou, I. and Foscolos, G.B. and Tsotinis, A. and Bourguignon, J.-J. and Serin, G. and Mirjolet, J.-F. and Dimas, K. and Kourafalos, V.N. and Eleutheriades, A. and Moutsos, V.I. and Khan, H. and Georgakopoulou, S. and Zaniou, A. and Prassa, M. and Theodoropoulou, M. and Pondiki, S. and Vamvakides, A.", journal = "BIOORGANIC AND MEDICINAL CHEMISTRY", year = "2012", volume = "20", number = "10", pages = "3323-3331", issn = "0968-0896", doi = "10.1016/j.bmc.2012.03.038", keywords = "1 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]piperazine; 1 cyclohexyl 4 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]piperazine; 1 ethyl 4 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]piperazine; 1 methyl 4 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]piperazine; 1 methyl 4 [alpha,a diphenyl(1 tricyclo[3.3.1.1 3,7]decyl)methyl]piperazine; 1 phenylmethyl 4 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]piperazine; 1 phenylmethyl 4 [alpha,a diphenyl(1 tricyclo[3.3.1.1 3,7]decyl)methyl]piperazine; 4 [4 [alpha (1 tricyclo[3.3.1.1 3,7]decyl)phenylmethyl]phenyl]morpholine; 4 [a,alpha diphenyl (1 tricyclo[3.3.1.1 3,7]decyl)methyl]morpholine; amantadine derivative; caspase 3; fluorouracil; gabapentin; gemcitabine; paclitaxel; piperazine derivative; sigma 1 opiate receptor; sigma 2 opiate receptor; sodium channel; unclassified drug, analgesic activity; animal experiment; animal model; antiproliferative activity; article; binding affinity; cancer cell; controlled study; drug cytotoxicity; drug design; drug screening; drug structure; drug synthesis; female; human; human cell; in vitro study; in vivo study; male; mouse; multiple cycle treatment; neuropathic pain; nonhuman; pancreas cancer; tumor xenograft, Adamantane; Animals; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Humans; Inhibitory Concentration 50; Mice; Mice, Nude; Molecular Structure; Pancreatic Neoplasms; Receptors, sigma, Agouti paca", abstract = "The synthesis of N-4-[a-(1-adamantyl)benzyl]phenylpiperazines 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. © 2012 Elsevier Ltd. All rights reserved." }