Most recent developments and modifications of 14-alkylamino and 14-alkoxy-4,5-epoxymorphinan derivatives
- PMID: 21861811
- PMCID: PMC3401597
- DOI: 10.2174/138955711797247752
Most recent developments and modifications of 14-alkylamino and 14-alkoxy-4,5-epoxymorphinan derivatives
Abstract
The 14-position of natural opiates (e.g. morphine) are unsubstituted, however synthetic approaches have uncovered that functionalizing position 14 gives rise to a wide range of diverse activities. This review focuses on SAR of the position, with the aim of aiding in the search for opioid analgesics with improved clinical profiles.
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References
-
- Block JH, Beale JM. Organic Medicinal and Pharmceutical Chemistry. Vol. 11. Lippincott Williams and Wilkins; Philadelphia: 2004.
-
- Fries DS. Principles of Medicinal Chemistry. Vol. 4. Williams and Wilkins; Philadelphia: 1995. Analgesics.
-
- Stein C, Schafer M, Machelska H. Attacking pain at its source: new perspectives on opioids. Nat Med. 2003;9(8):1003–1008. - PubMed
-
- Zieglgansberger W, Tolle TR, Zimprich A, Hollt V, Spanagel R. Endomorphins, Pain Relief, and Euphoria. Pain and the Brain. 1995;22:439–457.
-
- Kieffer BL, Evans CJ. Opioid tolerance-in search of the holy grail. Cell. 2002;108(5):587–590. - PubMed
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