New adamantane derivatives with sigma affinity and antiproliferative activity

Med Chem. 2012 Jul;8(4):569-86. doi: 10.2174/157340612801216201.

Abstract

The synthesis of 4-(1-adamantyl)-4,4-diarylbutylamines 1, 5-(1-adamantyl)-5,5-diarylpentylamines 2 and 6-(1-adamantyl)-6,6-diarylhexylamines 3 is described and the σ1, σ2-receptors and sodium channels binding affinity of compounds 1 were investigated. The in vitro activity of compounds 1, 2 and 3 against main cancer cell lines is significant. One of the most active analogs, 1a, had an interesting in vivo anticancer profile against the ovarian cancer cell line IGROV-1, which was associated with an anagelsic activity against the neuropathic pain induced by the main anticancer drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / chemical synthesis
  • Adamantane / chemistry*
  • Adamantane / pharmacology*
  • Adamantane / therapeutic use
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Binding Sites
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • Female
  • Humans
  • Male
  • Mice
  • Mice, SCID
  • Neoplasms / drug therapy
  • Receptors, sigma / chemistry*

Substances

  • Antineoplastic Agents
  • Receptors, sigma
  • Adamantane