Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators

Mark W. Irvine, Guangyu Fang, Richard Eaves, Maria B. Mayo-Martin, Erica S. Burnell, Blaise M. Costa, Georgia R. Culley, Arturas Volianskis, Graham L. Collingridge, Daniel T. Monaghan, David E. Jane

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Abstract 9-Substituted phenanthrene-3-carboxylic acids have been reported to have allosteric modulatory activity at the N-methyl-d-aspartate (NMDA) receptor. This receptor is activated by the excitatory neurotransmitter l-glutamate and has been implicated in a range of neurological disorders such as schizophrenia, epilepsy and chronic pain, and in neurodegenerative disorders such as Alzheimer's disease. Herein, the convenient synthesis of a wide range of novel 3,9-disubstituted phenanthrene derivatives starting from a few common intermediates is described. These new phenanthrene derivatives will help to clarify the structural requirements for allosteric modulation of the NMDA receptor.

Original languageEnglish (US)
Article numberss-2014-t0697-op
Pages (from-to)1593-1610
Number of pages18
JournalSynthesis (Germany)
Volume47
Issue number11
DOIs
Publication statusPublished - Dec 22 2015

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Keywords

  • NMDA receptor
  • Wittig reaction
  • allosteric modulators
  • palladium coupling
  • phenanthrenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Irvine, M. W., Fang, G., Eaves, R., Mayo-Martin, M. B., Burnell, E. S., Costa, B. M., ... Jane, D. E. (2015). Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators. Synthesis (Germany), 47(11), 1593-1610. [ss-2014-t0697-op]. https://doi.org/10.1055/s-0034-1380114