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. Epub 2012 Mar 24.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane* / chemical synthesis
  • Adamantane* / chemistry
  • Adamantane* / pharmacology
  • Animals
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Pancreatic Neoplasms / metabolism
  • Receptors, sigma / metabolism*

Substances

  • Antineoplastic Agents
  • Receptors, sigma
  • Adamantane