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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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

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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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