A New Useful Conversion Method of Naltrexone to 14-Deoxynaltrexone
| Autor: | Yoshihiro Ida, Hiroshi Nagase, Yumiko Yano, Yumiko Osa, Kimio Furuhata |
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| Rok vydání: | 2007 |
| Předmět: |
Pharmacology
medicine.drug_class Chemistry Organic Chemistry Acetal Ether General Medicine Combinatorial chemistry Naltrexone Analytical Chemistry chemistry.chemical_compound Thionyl chloride Opioid Opioid receptor Yield (chemistry) Pyridine medicine Organic chemistry Conversion method medicine.drug |
| Zdroj: | ChemInform. 38 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200723190 |
| Popis: | A novel synthetic method of 14-deoxynaltrexone (2), a μ-opioid receptor antagonist possessing a new message-structural part of opioid ligands, was established. Naltrexone methyl ether (5) was first converted to its acetal (24), followed by dehydration with thionyl chloride in pyridine to afford 8,14-dehydroderivative (26) of 24. The resulting unsaturated compound (26) was reduced with PtO 2 under hydrogen to give saturated compound (27), which was then acid-hydrolyzed to afford the desired 14-deoxynaltrexone (23) (3-0-methyl of 2) without degradation of the naltrexone skeleton. The total yield from naltrexone (1) to 23 was 86%. Finally, 23 was demethylated to give 14-deoxynaltrexone (2) in 85% yield. This method provides a useful reaction route to give various important intermediates as a message part to synthesize selectives ligands for the opioid receptor subtypes. |
| Databáze: | OpenAIRE |
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