Abstract
Acids 9a-f as possible bivalent ligands designed as a structural combination of opioid μ-agonist (Fentanyl) and NSAID (Indomethacin) activities and produced compounds which were tested as analgesics. The obtained series of compounds exhibits low affinity and activity both at opioid receptors and as cyclooxygenase (COX) inhibitors. One explanation of the weak opioid activity could be stereochemical peculiarities of these bivalent compounds which differ significantly from the fentanyl skeleton. The absence of significant COX inhibitory properties could be explained by the required substitution of an acyl fragment in the indomethacin structure for 4-piperidyl.
Original language | English (US) |
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Pages (from-to) | 5044-5053 |
Number of pages | 10 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 17 |
Issue number | 14 |
DOIs | |
State | Published - Jul 15 2009 |
Keywords
- Analgesics
- Indole
- NSAID
- Opioids
- Piperidine
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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CCDC 709587: Experimental Crystal Structure Determination
Vardanyan, R. (Creator), Vijay, G. (Creator), Nichol, G. S. (Creator), Liu, L. (Creator), Kumarasinghe, I. (Creator), Davis, P. (Creator), Vanderah, T. (Creator), Porreca, F. (Creator), Lai, J. (Creator) & Hruby, V. J. (Creator), Cambridge Crystallographic Data Centre, 2010
DOI: 10.5517/ccrtcxt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrtcxt&sid=DataCite
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