| Autor: |
Marton, János, Fekete, Anikó, Cumming, Paul, Hosztafi, Sándor, Mikecz, Pál, Henriksen, Gjermund |
| Jazyk: |
angličtina |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Marton, János; Fekete, Anikó; Cumming, Paul; Hosztafi, Sándor; Mikecz, Pál; Henriksen, Gjermund (2022). Diels-Alder Adducts of Morphinan-6,8-Dienes and Their Transformations. Molecules, 27(9) Molecular Diversity Preservation International MDPI 10.3390/molecules27092863 |
| ISSN: |
1420-3049 |
| Popis: |
6,14-ethenomorphinans are semisynthetic opiate derivatives containing an ethylene bridge between positions 6 and 14 in ring-C of the morphine skeleton that imparts a rigid molecular structure. These compounds represent an important family of opioid receptor ligands in which the 6,14-etheno bridged structural motif originates from a [4 + 2] cycloaddition of morphinan-6,8-dienes with dienophiles. Certain 6,14-ethenomorphinans having extremely high affinity for opioid receptors are often non-selective for opioid receptor subtypes, but this view is now undergoing some revision. The agonist 20R-etorphine and 20R-dihydroetorphine are several thousand times more potent analgesics than morphine, whereas diprenorphine is a high-affinity non-selective antagonist. The partial agonist buprenorphine is used as an analgesic in the management of post-operative pain or in substitution therapy for opiate addiction, sometimes in combination with the non-selective antagonist naloxone. In the context of the current opioid crisis, we communicated a summary of several decades of work toward generating opioid analgesics with lesser side effects or abuse potential. Our summary placed a focus on Diels–Alder reactions of morphinan-6,8-dienes and subsequent transformations of the cycloadducts. We also summarized the pharmacological aspects of radiolabeled 6,14-ethenomorphinans used in molecular imaging of opioid receptors. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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