Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors. / Conti, Paola; De Amici, Marco; Grazioso, Giovanni; Roda, Gabriella; Stensbøl, Tine B.; Bräuner-Osborne, Hans; Madsen, Ulf; Toma, Lucio; De Micheli, Carlo.

In: European Journal of Organic Chemistry, No. 22, 14.11.2003, p. 4455-4461.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Conti, P, De Amici, M, Grazioso, G, Roda, G, Stensbøl, TB, Bräuner-Osborne, H, Madsen, U, Toma, L & De Micheli, C 2003, 'Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors', European Journal of Organic Chemistry, no. 22, pp. 4455-4461. https://doi.org/10.1002/ejoc.200300424

APA

Conti, P., De Amici, M., Grazioso, G., Roda, G., Stensbøl, T. B., Bräuner-Osborne, H., Madsen, U., Toma, L., & De Micheli, C. (2003). Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors. European Journal of Organic Chemistry, (22), 4455-4461. https://doi.org/10.1002/ejoc.200300424

Vancouver

Conti P, De Amici M, Grazioso G, Roda G, Stensbøl TB, Bräuner-Osborne H et al. Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors. European Journal of Organic Chemistry. 2003 Nov 14;(22):4455-4461. https://doi.org/10.1002/ejoc.200300424

Author

Conti, Paola ; De Amici, Marco ; Grazioso, Giovanni ; Roda, Gabriella ; Stensbøl, Tine B. ; Bräuner-Osborne, Hans ; Madsen, Ulf ; Toma, Lucio ; De Micheli, Carlo. / Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors. In: European Journal of Organic Chemistry. 2003 ; No. 22. pp. 4455-4461.

Bibtex

@article{a35bcaed94db4d0f89f73d21264915bc,
title = "Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors",
abstract = "We have prepared four isomeric 3-hydroxycyclopentaisoxazohne amino acids 12-15, which represent analogues of glutamic acid having restricted conformations, through a strategy based on the 1,3-dipolar cycloaddition of bromonitrile oxide to a suitably protected 1-aminocyclopent-2-enecarboxylic acid. These target compounds proved to be inactive when assayed at ionotropic and metabotropic glutamate receptors, except for 12 which is an agonist primarily at mGluR5 (EC50 = 79 μM), but is less active at mGluR2 and only marginally active at mGluR1. The biological data are accounted for through comparison of the conformational profiles of the test compounds with that of reference agonists, i.e., N-methyl-D-aspartate (NMDA, 2), and 1-aminocyclopentane-1,3-dicarboxylic acids [trans-ACPD, 10; cis-ACPD, 11].",
keywords = "Amino acids, Glutamate analogues, Heterocycles, Receptors",
author = "Paola Conti and {De Amici}, Marco and Giovanni Grazioso and Gabriella Roda and Stensb{\o}l, {Tine B.} and Hans Br{\"a}uner-Osborne and Ulf Madsen and Lucio Toma and {De Micheli}, Carlo",
year = "2003",
month = nov,
day = "14",
doi = "10.1002/ejoc.200300424",
language = "English",
pages = "4455--4461",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "22",

}

RIS

TY - JOUR

T1 - Design of Cyclopentaisoxazoline Amino Acids as Conformationally Constrained Agonists at Glutamate Receptors

AU - Conti, Paola

AU - De Amici, Marco

AU - Grazioso, Giovanni

AU - Roda, Gabriella

AU - Stensbøl, Tine B.

AU - Bräuner-Osborne, Hans

AU - Madsen, Ulf

AU - Toma, Lucio

AU - De Micheli, Carlo

PY - 2003/11/14

Y1 - 2003/11/14

N2 - We have prepared four isomeric 3-hydroxycyclopentaisoxazohne amino acids 12-15, which represent analogues of glutamic acid having restricted conformations, through a strategy based on the 1,3-dipolar cycloaddition of bromonitrile oxide to a suitably protected 1-aminocyclopent-2-enecarboxylic acid. These target compounds proved to be inactive when assayed at ionotropic and metabotropic glutamate receptors, except for 12 which is an agonist primarily at mGluR5 (EC50 = 79 μM), but is less active at mGluR2 and only marginally active at mGluR1. The biological data are accounted for through comparison of the conformational profiles of the test compounds with that of reference agonists, i.e., N-methyl-D-aspartate (NMDA, 2), and 1-aminocyclopentane-1,3-dicarboxylic acids [trans-ACPD, 10; cis-ACPD, 11].

AB - We have prepared four isomeric 3-hydroxycyclopentaisoxazohne amino acids 12-15, which represent analogues of glutamic acid having restricted conformations, through a strategy based on the 1,3-dipolar cycloaddition of bromonitrile oxide to a suitably protected 1-aminocyclopent-2-enecarboxylic acid. These target compounds proved to be inactive when assayed at ionotropic and metabotropic glutamate receptors, except for 12 which is an agonist primarily at mGluR5 (EC50 = 79 μM), but is less active at mGluR2 and only marginally active at mGluR1. The biological data are accounted for through comparison of the conformational profiles of the test compounds with that of reference agonists, i.e., N-methyl-D-aspartate (NMDA, 2), and 1-aminocyclopentane-1,3-dicarboxylic acids [trans-ACPD, 10; cis-ACPD, 11].

KW - Amino acids

KW - Glutamate analogues

KW - Heterocycles

KW - Receptors

UR - http://www.scopus.com/inward/record.url?scp=0344442695&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200300424

DO - 10.1002/ejoc.200300424

M3 - Journal article

AN - SCOPUS:0344442695

SP - 4455

EP - 4461

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 22

ER -

ID: 379295810