Synthesis of 3-O-Carboxyalkyl Morphine Derivatives and Characterization of Their Acid-Base Properties.
NMR spectroscopy
O ligands
hapten
morphine
protonation
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Jul 2021
Jul 2021
Historique:
received:
23
02
2021
accepted:
18
05
2021
pubmed:
22
5
2021
medline:
18
9
2021
entrez:
21
5
2021
Statut:
ppublish
Résumé
The C-3 phenolic hydroxy group containing morphine derivatives (morphine, oxymorphone, naloxone, naltrexone) are excellent candidates for the synthesis of 3-O-functionalized molecules. Achieving free carboxylic group containing derivatives gives the opportunity for further modification and conjugation that could be used for immunization and immunoassays. For this purpose ethyl bromo- and chloroacetate can be used as O-alkylating agents. Hydrolyzing the products affords the appropriate free carboxylic group containing 3-O-carboxyalkyl derivatives. As these molecules contain an acidic and a basic functional group the protonation macro- and microconstants were determined too, using pH-potentiometry and NMR-pH titration, beside fully characterizing their structure using IR, CD, NMR and HR-MS measurements.
Identifiants
pubmed: 34018677
doi: 10.1002/cbdv.202100135
doi:
Substances chimiques
Morphine Derivatives
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2100135Subventions
Organisme : János Bolyai Research Scholarship of the Hungarian Academy of Sciences
Organisme : Bolyai+New National Excellence Program
ID : UNKP-20-5
Organisme : Ministry for Innovation and Technology
Informations de copyright
© 2021 The Authors. Chemistry & Biodiversity published by Wiley-VHCA AG, Zurich, Switzerland.
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