Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α1-adrenergic and 5-HT1A receptor binding sites recognition

Alessandro Bonifazi; Alessandro Piergentili; Fabio Del Bello; Yogita Farande; Mario Giannella; Maria Pigini; Consuelo Amantini; Massimo Nabissi; Valerio Farfariello; Giorgio Santoni; Elena Poggesi; Amedeo Leonardi; Sergio Menegon; Wilma Quaglia

doi:10.1021/jm301525w

Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α₁-adrenergic and 5-HT_1A receptor binding sites recognition

Alessandro Bonifazi
, Alessandro Piergentili
, Fabio Del Bello
, Yogita Farande
, Mario Giannella
, Maria Pigini
, Consuelo Amantini
, Massimo Nabissi
, Valerio Farfariello
, Giorgio Santoni
, Elena Poggesi
, Amedeo Leonardi
, Sergio Menegon
, Wilma Quaglia

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

21 Scopus citations

Abstract

5-HT_1A receptor and α₁-adrenoreceptor (α₁-AR) binding sites recognized by the 1,4-dioxanes 2-4 display reversed stereochemical requirements. (S)-2 proved to be a potent 5-HT_1A receptor agonist highly selective over α₁-AR subtypes. Chirality influenced the anticancer activity of 3 and 4 in human prostate cancer cells (PC-3): (R)-4, eutomer at the α_1d-AR subtype, was the most potent. The decreased effect of 4 and (R)-4 in α_1d-AR silenced PC-3 cells confirmed that their anticancer activity was α_1d-AR-dependent.

Original language	English (US)
Pages (from-to)	584-588
Number of pages	5
Journal	Journal of medicinal chemistry
Volume	56
Issue number	2
DOIs	https://doi.org/10.1021/jm301525w
State	Published - Jan 24 2013
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm301525w

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Bonifazi, A., Piergentili, A., Del Bello, F., Farande, Y., Giannella, M., Pigini, M., Amantini, C., Nabissi, M., Farfariello, V., Santoni, G., Poggesi, E., Leonardi, A., Menegon, S., & Quaglia, W. (2013). Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α₁-adrenergic and 5-HT_1A receptor binding sites recognition. Journal of medicinal chemistry, 56(2), 584-588. https://doi.org/10.1021/jm301525w

Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α₁-adrenergic and 5-HT_1A receptor binding sites recognition. / Bonifazi, Alessandro; Piergentili, Alessandro; Del Bello, Fabio et al.
In: Journal of medicinal chemistry, Vol. 56, No. 2, 24.01.2013, p. 584-588.

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

Bonifazi, A, Piergentili, A, Del Bello, F, Farande, Y, Giannella, M, Pigini, M, Amantini, C, Nabissi, M, Farfariello, V, Santoni, G, Poggesi, E, Leonardi, A, Menegon, S & Quaglia, W 2013, 'Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α₁-adrenergic and 5-HT_1A receptor binding sites recognition', Journal of medicinal chemistry, vol. 56, no. 2, pp. 584-588. https://doi.org/10.1021/jm301525w

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abstract = "5-HT1A receptor and α1-adrenoreceptor (α1-AR) binding sites recognized by the 1,4-dioxanes 2-4 display reversed stereochemical requirements. (S)-2 proved to be a potent 5-HT1A receptor agonist highly selective over α1-AR subtypes. Chirality influenced the anticancer activity of 3 and 4 in human prostate cancer cells (PC-3): (R)-4, eutomer at the α1d-AR subtype, was the most potent. The decreased effect of 4 and (R)-4 in α1d-AR silenced PC-3 cells confirmed that their anticancer activity was α1d-AR-dependent.",

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AU - Bonifazi, Alessandro

AU - Piergentili, Alessandro

AU - Del Bello, Fabio

AU - Farande, Yogita

AU - Giannella, Mario

AU - Pigini, Maria

AU - Amantini, Consuelo

AU - Nabissi, Massimo

AU - Farfariello, Valerio

AU - Santoni, Giorgio

AU - Poggesi, Elena

AU - Leonardi, Amedeo

AU - Menegon, Sergio

AU - Quaglia, Wilma

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AB - 5-HT1A receptor and α1-adrenoreceptor (α1-AR) binding sites recognized by the 1,4-dioxanes 2-4 display reversed stereochemical requirements. (S)-2 proved to be a potent 5-HT1A receptor agonist highly selective over α1-AR subtypes. Chirality influenced the anticancer activity of 3 and 4 in human prostate cancer cells (PC-3): (R)-4, eutomer at the α1d-AR subtype, was the most potent. The decreased effect of 4 and (R)-4 in α1d-AR silenced PC-3 cells confirmed that their anticancer activity was α1d-AR-dependent.

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Structure-activity relationships in 1,4-benzodioxan-related compounds. 11.(1) reversed enantioselectivity of 1,4-dioxane derivatives in α₁-adrenergic and 5-HT_1A receptor binding sites recognition

Abstract

ASJC Scopus subject areas

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