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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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Bioorganic & Medicinal Chemistry Letters, 2015, vol. 25, num. 19, p. 4250-4253

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Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)

# metadata.dc.title[].value
Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold