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American Chemical Society, Journal of Medicinal Chemistry, 2(56), p. 584-588, 2013

DOI: 10.1021/jm301525w

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Structure–Activity Relationships in 1,4-Benzodioxan-Related Compounds. 11. Reversed Enantioselectivity of 1,4-Dioxane Derivatives in α1-Adrenergic and 5-HT1A Receptor Binding Sites Recognition

Journal article published in 2013 by Alessandro Bonifazi, Alessandro Piergentili, Fabio Del Bello, Yogita Farande, Mario Giannella, Maria Pigini, Consuelo Amantini, Massimo Nabissi ORCID, Valerio Farfariello, Giorgio Santoni, Elena Poggesi, Amedeo Leonardi, Sergio Menegon, Wilma Quaglia
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

5-HT1A receptor and α1-adrenoreceptor (α1-AR) binding sites recognized by the 1,4-dioxane compounds 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.