Cyclic Biphalin Analogues Incorporating a Xylene Bridge: Synthesis, Characterization, and Biological Profile

Stefanucci, Azzurra and Carotenuto, Alfonso and Macedonio, Giorgia and Novellino, Ettore and Pieretti, Stefano and Szűcs, Edina and Erdei, Anna and Zádor, Ferenc and Benyhe, Sándor (2017) Cyclic Biphalin Analogues Incorporating a Xylene Bridge: Synthesis, Characterization, and Biological Profile. ACS MEDICINAL CHEMISTRY LETTERS, 8 (8). pp. 858-863. ISSN 1948-5875

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Abstract

In this work we enhanced the ring lipophilicity of biphalin introducing a xylene moiety, thus obtaining three cyclic regioisomers. Novel compounds have similar in vitro activity as the parent compound, but one of these (6a) shows a remarkable increase of in vivo antinociceptive effect. Nociception tests have disclosed its significant high potency and the more prolonged effect in eliciting analgesia, higher than that of biphalin and of the disulfide-bridge-containing analogue (7).

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