Synthesis of a Series of Novel 3,9-Disubstituted Phenanthrenes as Analogues of Known N-Methyl-D-aspartate Receptor Allosteric Modulators

被引：9

作者：

Irvine, Mark W. ^{[1
]}

Fang, Guangyu ^{[1
]}

Eaves, Richard ^{[1
]}

Mayo-Martin, Maria B. ^{[1
]}

Burnell, Erica S. ^{[1
]}

Costa, Blaise M. ^{[2
]}

Culley, Georgia R. ^{[1
]}

Volianskis, Arturas ^{[1
]}

Collingridge, Graham L. ^{[1
]}

Monaghan, Daniel T. ^{[2
]}

Jane, David E. ^{[1
]}

机构：

[1] Univ Bristol, Sch Physiol & Pharmacol, Bristol BS8 1TD, Avon, England

[2] Univ Nebraska Med Ctr, Dept Pharmacol & Expt Neurosci, Omaha, NE 68198 USA

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 11期

基金：

英国生物技术与生命科学研究理事会; 美国国家卫生研究院;

关键词：

phenanthrenes; NMDA receptor; allosteric modulators; palladium coupling; Wittig reaction; NMDA RECEPTOR; DERIVATIVES; ACIDS;

D O I：

10.1055/s-0034-1380114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1593 / 1610

页数：18

共 10 条

[1] The NMDA receptor as a target for cognitive enhancement
Collingridge, Graham L.
Volianskis, Arturas
Bannister, Neil
France, Grace
Hanna, Lydia
Mercier, Marion
Tidball, Patrick
Fang, Guangyu
Irvine, Mark W.
Costa, Blaise M.
Monaghan, Daniel T.
Bortolotto, Zuner A.
Molnar, Elek
Lodge, David
Jane, David E.
[J]. NEUROPHARMACOLOGY, 2013, 64 : 13 - 26
[2] Costa B. M., 2010, JPET, V337, P614
[3] PHENANTHRYLALKANOIC ACIDS .4. SYNTHESES AND ANTIINFLAMMATORY ACTIVITY OF 2-PHENANTHRYL DERIVATIVE, 3-PHENANTHRYL DERIVATIVE, AND 9-PHENANTHRYL DERIVATIVE AND 9-CHLORO-3-PHENANTHRYL DERIVATIVE OF PROPANOIC ACID
FERNANDEZ, F
GONZALEZ, C
GOMEZ, G
LOPEZ, C
MEDINA, L
CALLEJA, JM
CANO, E
[J]. ARCHIV DER PHARMAZIE, 1990, 323 (04) : 239 - 242
[4] Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors
Irvine, Mark W.
Costa, Blaise M.
Dlaboga, Daniel
Culley, Georgia R.
Hulse, Richard
Scholefield, Caroline L.
Atlason, Palmi
Fang, Guangyu
Eaves, Richard
Morley, Richard
Mayo-Martin, Maria B.
Amici, Mascia
Bortolotto, Zuner A.
Donaldson, Lucy
Collingridge, Graham L.
Molnar, Elek
Monaghan, Daniel T.
Jane, David E.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (01) : 327 - 341
[5] Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction
Klapars, A
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) : 14844 - 14845
[6] Natural phenanthrenes and their biological activity
Kovacs, Adriana
Vasas, Andrea
Hohmann, Judit
[J]. PHYTOCHEMISTRY, 2008, 69 (05) : 1084 - 1110
[7] Pharmacological modulation of NMDA receptor activity and the advent of negative and positive allosteric modulators
Monaghan, Daniel T.
Irvine, Mark W.
Costa, Blaise Mathias
Fang, Guangyu
Jane, David E.
[J]. NEUROCHEMISTRY INTERNATIONAL, 2012, 61 (04) : 581 - 592
[8] Studies in the phenanthrene series. II. Phenanthrene carboxylic acids and 9-bromophenanthrene derivatives
Mosettig, E
de Kamp, JV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 : 3328 - 3337
[9] A new general method for the preparation of N-sulfonyloxaziridines
Ruano, JLG
Alemán, J
Fajardo, C
Parra, A
[J]. ORGANIC LETTERS, 2005, 7 (24) : 5493 - 5496
[10] ATTEMPTS TO FIND NEW ANTIMALARIALS .11. DERIVATIVES OF PHENANTHRENE .3. AMINO ALCOHOLS DERIVED FROM 9-CHLOROPHENANTHRENE
SCHULTZ, J
GOLDBERG, MA
ORDAS, EP
CARSCH, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1946, 11 (04) : 320 - 328

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