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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Published inJournal of organic chemistry Vol. 78; no. 7; pp. 2914 - 2925
Main Authors Giacometti, Robert D, Duchek, Jan, Werner, Lukas, Husni, Afeef S, McCurdy, Christopher R, Cutler, Stephen J, Cox, D. Phillip, Hudlicky, Tomas
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2013
Amer Chemical Soc
Subjects
Animals
Chemistry
Chemistry, Organic
CHO Cells
Cricetinae
Cyclization
Dose-Response Relationship, Drug
Humans
Hydrocodone - chemical synthesis
Hydrocodone - chemistry
Hydrocodone - pharmacology
Molecular Structure
Narcotic Antagonists
Physical Sciences
Science & Technology
Structure-Activity Relationship
OPIOID RECEPTORS
MORPHINE
AGONISTS
PHOSPHINIC ACIDS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo3026753