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

4 Citations (Scopus)

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
StatePublished - Dec 22 2015

Fingerprint

Phenanthrenes
N-Methyl-D-Aspartate Receptors
Modulators
Derivatives
Carboxylic acids
Modulation
Carboxylic Acids
Neurotransmitter Agents
Glutamic Acid
phenanthrene
aspartic acid receptor

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

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

Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators. / Irvine, Mark W.; Fang, Guangyu; Eaves, Richard; Mayo-Martin, Maria B.; Burnell, Erica S.; Costa, Blaise M.; Culley, Georgia R.; Volianskis, Arturas; Collingridge, Graham L.; Monaghan, Daniel T; Jane, David E.

In: Synthesis (Germany), Vol. 47, No. 11, ss-2014-t0697-op, 22.12.2015, p. 1593-1610.

Research output: Contribution to journalArticle

Irvine, MW, Fang, G, Eaves, R, Mayo-Martin, MB, Burnell, ES, Costa, BM, Culley, GR, Volianskis, A, Collingridge, GL, Monaghan, DT & Jane, DE 2015, 'Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators', Synthesis (Germany), vol. 47, no. 11, ss-2014-t0697-op, pp. 1593-1610. https://doi.org/10.1055/s-0034-1380114
Irvine, Mark W. ; Fang, Guangyu ; Eaves, Richard ; Mayo-Martin, Maria B. ; Burnell, Erica S. ; Costa, Blaise M. ; Culley, Georgia R. ; Volianskis, Arturas ; Collingridge, Graham L. ; Monaghan, Daniel T ; Jane, David E. / Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators. In: Synthesis (Germany). 2015 ; Vol. 47, No. 11. pp. 1593-1610.
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