(S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation.

Research output: Contribution to journalJournal articleResearchpeer-review

Standard

(S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation. / Brogi, Simone; Brindisi, Marghertia; Butini, Stefania; Kshirsagar, Giridhar; Maramai, Samuele; Chemi, Giulia; Gemma, Sandra; Campiani, Giuseppe; Novellino, Ettore; Fiorenzani, Paolo; Pinassi, Jessica; Aloisi, Anna Maria; Gynther, Mikko; Venskutonyte, Raminta; Han, Liwei; Frydenvang, Karla Andrea; Kastrup, Jette Sandholm Jensen; Pickering, Darryl S.

In: Journal of Medicinal Chemistry, Vol. 61, No. 5, 08.03.2018, p. 2124-2130.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Brogi, S, Brindisi, M, Butini, S, Kshirsagar, G, Maramai, S, Chemi, G, Gemma, S, Campiani, G, Novellino, E, Fiorenzani, P, Pinassi, J, Aloisi, AM, Gynther, M, Venskutonyte, R, Han, L, Frydenvang, KA, Kastrup, JSJ & Pickering, DS 2018, '(S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation.', Journal of Medicinal Chemistry, vol. 61, no. 5, pp. 2124-2130. https://doi.org/10.1021/acs.jmedchem.8b00099

APA

Brogi, S., Brindisi, M., Butini, S., Kshirsagar, G., Maramai, S., Chemi, G., ... Pickering, D. S. (2018). (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation. Journal of Medicinal Chemistry, 61(5), 2124-2130. https://doi.org/10.1021/acs.jmedchem.8b00099

Vancouver

Brogi S, Brindisi M, Butini S, Kshirsagar G, Maramai S, Chemi G et al. (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation. Journal of Medicinal Chemistry. 2018 Mar 8;61(5):2124-2130. https://doi.org/10.1021/acs.jmedchem.8b00099

Author

Brogi, Simone ; Brindisi, Marghertia ; Butini, Stefania ; Kshirsagar, Giridhar ; Maramai, Samuele ; Chemi, Giulia ; Gemma, Sandra ; Campiani, Giuseppe ; Novellino, Ettore ; Fiorenzani, Paolo ; Pinassi, Jessica ; Aloisi, Anna Maria ; Gynther, Mikko ; Venskutonyte, Raminta ; Han, Liwei ; Frydenvang, Karla Andrea ; Kastrup, Jette Sandholm Jensen ; Pickering, Darryl S. / (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation. In: Journal of Medicinal Chemistry. 2018 ; Vol. 61, No. 5. pp. 2124-2130.

Bibtex

@article{71a01ea322054860b3e7c9dcd5644931,
title = "(S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation.",
abstract = "Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAR analysis. Interesting binding properties at GluA2, GluK1 and GluK3 receptors were discovered. The requirements for GluK3 interaction were elucidated determining the X-ray structures of the GluK3-LBD with 2 and 5c and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).",
author = "Simone Brogi and Marghertia Brindisi and Stefania Butini and Giridhar Kshirsagar and Samuele Maramai and Giulia Chemi and Sandra Gemma and Giuseppe Campiani and Ettore Novellino and Paolo Fiorenzani and Jessica Pinassi and Aloisi, {Anna Maria} and Mikko Gynther and Raminta Venskutonyte and Liwei Han and Frydenvang, {Karla Andrea} and Kastrup, {Jette Sandholm Jensen} and Pickering, {Darryl S}",
year = "2018",
month = "3",
day = "8",
doi = "10.1021/acs.jmedchem.8b00099",
language = "English",
volume = "61",
pages = "2124--2130",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "5",

}

RIS

TY - JOUR

T1 - (S)-2-Amino-3-(5-methyl-3-hydroxyisoxazol-4-yl)propanoic Acid (AMPA) and Kainate Receptor Ligands: Further Exploration of Bioisosteric Replacements, Structural and Biological Investigation.

AU - Brogi, Simone

AU - Brindisi, Marghertia

AU - Butini, Stefania

AU - Kshirsagar, Giridhar

AU - Maramai, Samuele

AU - Chemi, Giulia

AU - Gemma, Sandra

AU - Campiani, Giuseppe

AU - Novellino, Ettore

AU - Fiorenzani, Paolo

AU - Pinassi, Jessica

AU - Aloisi, Anna Maria

AU - Gynther, Mikko

AU - Venskutonyte, Raminta

AU - Han, Liwei

AU - Frydenvang, Karla Andrea

AU - Kastrup, Jette Sandholm Jensen

AU - Pickering, Darryl S

PY - 2018/3/8

Y1 - 2018/3/8

N2 - Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAR analysis. Interesting binding properties at GluA2, GluK1 and GluK3 receptors were discovered. The requirements for GluK3 interaction were elucidated determining the X-ray structures of the GluK3-LBD with 2 and 5c and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

AB - Starting from 1-4 and 7 structural templates, analogues based on bioisosteric replacements (5a-c vs 1, 2 and 6 vs 7) were synthesized for completing the SAR analysis. Interesting binding properties at GluA2, GluK1 and GluK3 receptors were discovered. The requirements for GluK3 interaction were elucidated determining the X-ray structures of the GluK3-LBD with 2 and 5c and by computational studies. Antinociceptive potential was demonstrated for GluK1 partial agonist 3 and antagonist 7 (2 mg/kg ip).

U2 - 10.1021/acs.jmedchem.8b00099

DO - 10.1021/acs.jmedchem.8b00099

M3 - Journal article

C2 - 29451794

VL - 61

SP - 2124

EP - 2130

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 5

ER -

ID: 189836867