Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested...

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Veröffentlicht in:Journal of organic chemistry 2013-04, Vol.78 (7), p.2914-2925
Hauptverfasser: Giacometti, Robert D, Duchek, Jan, Werner, Lukas, Husni, Afeef S, McCurdy, Christopher R, Cutler, Stephen J, Cox, D. Phillip, Hudlicky, Tomas
Format: Artikel
Sprache:eng
Schlagworte:
Animals
bioactive properties
chemical reactions
chemical structure
CHO Cells
Cricetinae
Cyclization
Dose-Response Relationship, Drug
ethylene glycol
Humans
Hydrocodone - chemical synthesis
Hydrocodone - chemistry
Hydrocodone - pharmacology
Molecular Structure
Narcotic Antagonists
organic chemistry
oxygen
Structure-Activity Relationship
sulfur
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Zusammenfassung:Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo3026753