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

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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
Article number	ss-2014-t0697-op
Pages (from-to)	1593-1610
Number of pages	18
Journal	Synthesis (Germany)
Volume	47
Issue number	11
Early online date	19 Mar 2015
DOIs	https://doi.org/10.1055/s-0034-1380114
Publication status	Published - Jun 2015

Keywords

allosteric modulators
NMDA receptor
palladium coupling
phenanthrenes
Wittig reaction

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10.1055/s-0034-1380114

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This is the final published version of the article (version of record). It first appeared online via Thieme Publishing at http://dx.doi.org/10.1055/s-0034-1380114. Please refer to any applicable terms of use of the publisher.
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This is the final published version of the article (version of record). It first appeared online via Thieme Publishing at http://dx.doi.org/10.1055/s-0034-1380114. Please refer to any applicable terms of use of the publisher.
Final published version, 3.21 MBLicence: CC BY

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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

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

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.}",

year = "2015",

month = jun,

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

language = "English",

volume = "47",

pages = "1593--1610",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "11",

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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

TY - JOUR

T1 - Synthesis of a series of novel 3,9-disubstituted phenanthrenes as analogues of known N-methyl-D-aspartate receptor allosteric modulators

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.

PY - 2015/6

Y1 - 2015/6

N2 - 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 - 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.

KW - allosteric modulators

KW - NMDA receptor

KW - palladium coupling

KW - phenanthrenes

KW - Wittig reaction

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ER -

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

Abstract

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Identifying the role of NMDA receptors in STP through investigation of synaptic plasticity and discovery of novel subtype-specific antagonists

Molecular mechanisms of long-term Depression int the hippocampus

DISCOVERING NOVEL SUBTYPE-SELECTIVE GLUTAMATE RECEPTOR ANTAGONISTS FOR THE STUDY OF HIPPOCAMPUL SYNAPTIC PLASTICITY

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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

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

Identifying the role of NMDA receptors in STP through investigation of synaptic plasticity and discovery of novel subtype-specific antagonists

Molecular mechanisms of long-term Depression int the hippocampus

DISCOVERING NOVEL SUBTYPE-SELECTIVE GLUTAMATE RECEPTOR ANTAGONISTS FOR THE STUDY OF HIPPOCAMPUL SYNAPTIC PLASTICITY

Cite this