New synthesis of 6 [3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid and evaluation of the influence of adamantyl group on the DNA binding of a naphthoic …

…, E Gorincioi, M Rajabi, G Vistoli, E Santaniello

Index: Milanese, Alberto; Gorincioi, Elena; Rajabi, Mehdi; Vistoli, Giulio; Santaniello, Enzo Bioorganic Chemistry, 2011 , vol. 39, # 4 p. 151 - 158

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Citation Number: 5

Abstract

6 [3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene®), a synthetic aromatic retinoid specific for RARβ and RARγ receptors, has been prepared utilizing a Pd/C- mediated Suzuki coupling between 6-bromo-2-naphthoic acid and 4-methoxyphenyl boronic acid, followed by introduction of an adamantyl group in the position 3 of the formed 6-(4- methoxyphenyl)-2-naphthoic acid. The interaction of 6-(4-methoxyphenyl)-2-naphthoic ...