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

Azzurra Stefanucci, Alfonso Carotenuto, Giorgia Macedonio, Ettore Novellino, Stefano Pieretti, Francesca Marzoli, Edina Szücs, Anna I. Erdei, Ferenc Zádor, Sándor Benyhe, Adriano Mollica

Research output: Contribution to journalArticle

7 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)858-863
Number of pages6
JournalACS Medicinal Chemistry Letters
Volume8
Issue number8
DOIs
Publication statusPublished - Aug 10 2017

Keywords

  • Biphalin
  • CLIPS technology
  • antinociception
  • opioids
  • xylene bridge

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Stefanucci, A., Carotenuto, A., Macedonio, G., Novellino, E., Pieretti, S., Marzoli, F., Szücs, E., Erdei, A. I., Zádor, F., Benyhe, S., & Mollica, A. (2017). Cyclic Biphalin Analogues Incorporating a Xylene Bridge: Synthesis, Characterization, and Biological Profile. ACS Medicinal Chemistry Letters, 8(8), 858-863. https://doi.org/10.1021/acsmedchemlett.7b00210