Cyclic Biphalin Analogues Incorporating a Xylene Bridge: Synthesis, Characterization, and Biological Profile
| Autor: | Ettore Novellino, Azzurra Stefanucci, Adriano Mollica, Francesca Marzoli, Edina Szűcs, Giorgia Macedonio, Anna I. Erdei, Alfonso Carotenuto, Sándor Benyhe, Ferenc Zádor, Stefano Pieretti |
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| Přispěvatelé: | Stefanucci, Azzurra, Carotenuto, Alfonso, Macedonio, Giorgia, Novellino, Ettore, Pieretti, Stefano, Marzoli, Francesca, Szűcs, Edina, Erdei, Anna I, Zádor, Ferenc, Benyhe, Sándor, Mollica, Adriano |
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
xylene bridge Chemistry Stereochemistry Organic Chemistry Xylene Biphalin 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry In vitro 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology In vivo Drug Discovery Lipophilicity opioid Structural isomer Moiety antinociception CLIPS technology |
| Zdroj: | ACS Medicinal Chemistry Letters. 8:858-863 |
| ISSN: | 1948-5875 |
| DOI: | 10.1021/acsmedchemlett.7b00210 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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