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cc-by-nc-nd (c) Elsevier Ltd, 2015
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/128385

Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold

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The adamantane scaffold is found in several marketed drugs and in many investigational 11b-HSD1 inhibitors. Interestingly, all the clinically approved adamantane derivatives are C-1 substituted. We demonstrate that, in a series of paired adamantane isomers, substitution of the adamantane in C-2 is preferred over the substitution at C-1 and is necessary for potency at human 11b-HSD1. Furthermore, the introduction of an oxygen atom in the hydrocarbon scaffold of adamantane is deleterious to 11b-HSD1 inhibition. Molecular modeling studies provide a basis to rationalize these features.

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LEIVA MARTÍNEZ, Rosana, et al. Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold. Bioorganic & Medicinal Chemistry Letters. 2015. Vol. 25, num. 19, pags. 4250-4253. ISSN 0960-894X. [consulted: 8 of June of 2026]. Available at: https://hdl.handle.net/2445/128385

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