Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist

María L. López-Rodríguez; Ma José Morcillo; Esther Fernández; Bellinda Benhamú; Ignacio Tejada; David Ayala; Alma Viso; Mireia Olivella; Leonardo Pardo; Mercedes Delgado; Jorge Manzanares; José A. Fuentes

doi:10.1016/S0960-894X(03)00160-4

Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist

María L. López-Rodríguez, Ma José Morcillo, Esther Fernández, Bellinda Benhamú, Ignacio Tejada, David Ayala, Alma Viso, Mireia Olivella, Leonardo Pardo, Mercedes Delgado, Jorge Manzanares, José A. Fuentes

Research output: Contribution to journal › Article › Research › peer-review

20 Citations (Scopus)

Abstract

Based on a computational model for 5-HT1AR-ligand interaction and QSAR studies, we have designed and synthesized a new series of arylpiperazines 2-8 which exhibit high 5-HT1AR affinity and selectivity over α1-adrenergic receptors. Among them, compound CSP-2503 (4) has been pharmacologically characterized as a 5-HT1AR agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic properties. © 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1429-1432
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	13
Issue number	8
DOIs	https://doi.org/10.1016/S0960-894X(03)00160-4
Publication status	Published - 17 Apr 2003

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López-Rodríguez, M. L., Morcillo, M. J., Fernández, E., Benhamú, B., Tejada, I., Ayala, D., Viso, A., Olivella, M., Pardo, L., Delgado, M., Manzanares, J., & Fuentes, J. A. (2003). Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist. Bioorganic and Medicinal Chemistry Letters, 13(8), 1429-1432. https://doi.org/10.1016/S0960-894X(03)00160-4

López-Rodríguez, María L. ; Morcillo, Ma José ; Fernández, Esther ; Benhamú, Bellinda ; Tejada, Ignacio ; Ayala, David ; Viso, Alma ; Olivella, Mireia ; Pardo, Leonardo ; Delgado, Mercedes ; Manzanares, Jorge ; Fuentes, José A. / Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist. In: Bioorganic and Medicinal Chemistry Letters. 2003 ; Vol. 13, No. 8. pp. 1429-1432.

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title = "Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT1A receptor agonist",

abstract = "Based on a computational model for 5-HT1AR-ligand interaction and QSAR studies, we have designed and synthesized a new series of arylpiperazines 2-8 which exhibit high 5-HT1AR affinity and selectivity over α1-adrenergic receptors. Among them, compound CSP-2503 (4) has been pharmacologically characterized as a 5-HT1AR agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic properties. {\textcopyright} 2003 Elsevier Science Ltd. All rights reserved.",

author = "L{\'o}pez-Rodr{\'i}guez, {Mar{\'i}a L.} and Morcillo, {Ma Jos{\'e}} and Esther Fern{\'a}ndez and Bellinda Benham{\'u} and Ignacio Tejada and David Ayala and Alma Viso and Mireia Olivella and Leonardo Pardo and Mercedes Delgado and Jorge Manzanares and Fuentes, {Jos{\'e} A.}",

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doi = "10.1016/S0960-894X(03)00160-4",

language = "English",

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López-Rodríguez, ML, Morcillo, MJ, Fernández, E, Benhamú, B, Tejada, I, Ayala, D, Viso, A, Olivella, M, Pardo, L, Delgado, M, Manzanares, J & Fuentes, JA 2003, 'Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist', Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 8, pp. 1429-1432. https://doi.org/10.1016/S0960-894X(03)00160-4

Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist. / López-Rodríguez, María L.; Morcillo, Ma José; Fernández, Esther; Benhamú, Bellinda; Tejada, Ignacio; Ayala, David; Viso, Alma; Olivella, Mireia; Pardo, Leonardo; Delgado, Mercedes; Manzanares, Jorge; Fuentes, José A.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 13, No. 8, 17.04.2003, p. 1429-1432.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT1A receptor agonist

AU - López-Rodríguez, María L.

AU - Morcillo, Ma José

AU - Fernández, Esther

AU - Benhamú, Bellinda

AU - Tejada, Ignacio

AU - Ayala, David

AU - Viso, Alma

AU - Olivella, Mireia

AU - Pardo, Leonardo

AU - Delgado, Mercedes

AU - Manzanares, Jorge

AU - Fuentes, José A.

PY - 2003/4/17

Y1 - 2003/4/17

N2 - Based on a computational model for 5-HT1AR-ligand interaction and QSAR studies, we have designed and synthesized a new series of arylpiperazines 2-8 which exhibit high 5-HT1AR affinity and selectivity over α1-adrenergic receptors. Among them, compound CSP-2503 (4) has been pharmacologically characterized as a 5-HT1AR agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic properties. © 2003 Elsevier Science Ltd. All rights reserved.

AB - Based on a computational model for 5-HT1AR-ligand interaction and QSAR studies, we have designed and synthesized a new series of arylpiperazines 2-8 which exhibit high 5-HT1AR affinity and selectivity over α1-adrenergic receptors. Among them, compound CSP-2503 (4) has been pharmacologically characterized as a 5-HT1AR agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic properties. © 2003 Elsevier Science Ltd. All rights reserved.

U2 - 10.1016/S0960-894X(03)00160-4

DO - 10.1016/S0960-894X(03)00160-4

M3 - Article

VL - 13

SP - 1429

EP - 1432

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 8

ER -

López-Rodríguez ML, Morcillo MJ, Fernández E, Benhamú B, Tejada I, Ayala D et al. Design and synthesis of S-(-)-2-[[4-(napht-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2- a]pyrazine (CSP-2503) using computational simulation. A 5-HT<inf>1A</inf> receptor agonist. Bioorganic and Medicinal Chemistry Letters. 2003 Apr 17;13(8):1429-1432. https://doi.org/10.1016/S0960-894X(03)00160-4