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

doi: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

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

Pharmacology & Experimental Neuroscience (PEN)

Research output: Contribution to journal › Article › peer-review

9 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 language	English (US)
Article number	ss-2014-t0697-op
Pages (from-to)	1593-1610
Number of pages	18
Journal	Synthesis (Germany)
Volume	47
Issue number	11
DOIs	https://doi.org/10.1055/s-0034-1380114
State	Published - Dec 22 2015

Keywords

NMDA receptor
Wittig reaction
allosteric modulators
palladium coupling
phenanthrenes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0034-1380114

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Irvine, M. W., Fang, G., Eaves, R., Mayo-Martin, M. B., Burnell, E. S., Costa, B. M., Culley, G. R., Volianskis, A., Collingridge, G. L., Monaghan, D. T., & 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. Article ss-2014-t0697-op. https://doi.org/10.1055/s-0034-1380114

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

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

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.",

keywords = "NMDA receptor, Wittig reaction, allosteric modulators, palladium coupling, phenanthrenes",

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

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doi = "10.1055/s-0034-1380114",

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AU - Irvine, Mark W.

AU - Fang, Guangyu

AU - Eaves, Richard

AU - Mayo-Martin, Maria B.

AU - Burnell, Erica S.

AU - Costa, Blaise M.

AU - Culley, Georgia R.

AU - Volianskis, Arturas

AU - Collingridge, Graham L.

AU - Monaghan, Daniel T.

AU - Jane, David E.

N1 - Publisher Copyright: © Georg Thieme Verlag.

PY - 2015/12/22

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N2 - 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.

AB - 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.

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KW - palladium coupling

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

Abstract

Keywords

ASJC Scopus subject areas

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