Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

Andrea Pinto; Lucia Tamborini; Federica Mastronardi; Roberta Ettari; Diego Romano; Birgitte Nielsen; Carlo De Micheli; Paola Conti

doi:10.1016/j.bmcl.2014.02.058

Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

Andrea Pinto, Lucia Tamborini, Federica Mastronardi, Roberta Ettari, Diego Romano, Birgitte Nielsen, Carlo De Micheli, Paola Conti

3 Citationer (Scopus)

Abstract

A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists.

Originalsprog	Engelsk
Tidsskrift	Bioorganic and Medicinal Chemistry Letters
Vol/bind	24
Udgave nummer	8
Sider (fra-til)	1980-1982
Antal sider	3
DOI	https://doi.org/10.1016/j.bmcl.2014.02.058
Status	Udgivet - 15 apr. 2014

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10.1016/j.bmcl.2014.02.058

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Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors. / Pinto, Andrea; Tamborini, Lucia; Mastronardi, Federica et al.

I: Bioorganic and Medicinal Chemistry Letters, Bind 24, Nr. 8, 15.04.2014, s. 1980-1982.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

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abstract = "A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists.",

author = "Andrea Pinto and Lucia Tamborini and Federica Mastronardi and Roberta Ettari and Diego Romano and Birgitte Nielsen and {De Micheli}, Carlo and Paola Conti",

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doi = "10.1016/j.bmcl.2014.02.058",

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T1 - Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

AU - Pinto, Andrea

AU - Tamborini, Lucia

AU - Mastronardi, Federica

AU - Ettari, Roberta

AU - Romano, Diego

AU - Nielsen, Birgitte

AU - De Micheli, Carlo

AU - Conti, Paola

PY - 2014/4/15

Y1 - 2014/4/15

N2 - A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists.

AB - A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists.

U2 - 10.1016/j.bmcl.2014.02.058

DO - 10.1016/j.bmcl.2014.02.058

M3 - Journal article

C2 - 24630559

SN - 0960-894X

VL - 24

SP - 1980

EP - 1982

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 8

ER -

Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

Abstract

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