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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Synthesis and In Silico Profile Modeling of 6-O-Fluoroalkyl-6-O-desmethyl-diprenorphine Analogs

by
János Marton
1,*,†,
Dávid Gombos
2,3,†,
Paul Cumming
4,5,
Tamás Fehér
2,6,
Alexander Milentyev
1,
Beate Bauer
1,
Frode Willoch
7,
Bent Wilhelm Schoultz
8,9,
Sándor Benyhe
2 and
Ferenc Ötvös
2,*
1
ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany
2
Institute of Biochemistry, HUN-REN Biological Research Center, Temesvári krt. 62, H-6726 Szeged, Hungary
3
Doctoral School of Theoretical Medicine, Faculty of Medicine, University of Szeged, Dugonics tér 13, H-6720 Szeged, Hungary
4
School of Psychology and Counselling, Queensland University of Technology, Brisbane, QLD 4059, Australia
5
Department of Nuclear Medicine, Bern University Hospital, Freiburgstraße 18, CH-3010 Bern, Switzerland
6
Synthetic and Systems Biology Unit, HUN-REN Biological Research Center, 62 Temesvari krt., H-6726 Szeged, Hungary
7
Institute of Basic Medical Sciences, University of Oslo, P. O. Box 1110, Blindern, N-0317 Oslo, Norway
8
Department of Physics, University of Oslo, P.O. Box 1048, Blindern, N-0316 Oslo, Norway
9
Norwegian Medical Cyclotron Centre Ltd., Sognsvannsveien 20, N-0372 Oslo, Norway
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Int. J. Mol. Sci. 2025, 26(19), 9427; https://doi.org/10.3390/ijms26199427
Submission received: 1 September 2025 / Revised: 16 September 2025 / Accepted: 18 September 2025 / Published: 26 September 2025
(This article belongs to the Section Materials Science)
Review Reports Versions Notes

Abstract

We present the first preparation of novel 6-O-(fluoroalkyl)-6-O-desmethyl-diprenorphine analogs and 6-O-(tosyloxyalkyl)-6-O-desmethyl-3-O-trityl-diprenorphine-type precursors for the radiosynthesis of 6-O-([18F]fluoroalkyl)-6-O-desmethyl-diprenorphine radiotracers for molecular imaging by positron emission tomography (PET). The synthesis sequence to the new opioid receptor ligands consists of eleven steps starting from the poppy alkaloid thebaine. The precursor molecules were prepared in a three-step synthesis process from the «Luthra precursor» (TDDPN). We report the complete 1H- and 13C-NMR assignment of the new 6-O-(substituted)-6-O-desmethyl-diprenorphine derivatives, as well as the results of docking studies in silico for diverse novel opioid receptor ligands, including a new series of 6-O-(fluoroalkyl)- and 6-O-(hydroxyalkyl)-6-O-desmethyl-diprenorphine derivatives.
Keywords: opioid receptors; 6,14-ethenomorphinans; diprenorphine; 6-O-fluoroalkyl-6-O-desmethyl-diprenorphine; in silico docking; positron emission tomography opioid receptors; 6,14-ethenomorphinans; diprenorphine; 6-O-fluoroalkyl-6-O-desmethyl-diprenorphine; in silico docking; positron emission tomography

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MDPI and ACS Style

Marton, J.; Gombos, D.; Cumming, P.; Fehér, T.; Milentyev, A.; Bauer, B.; Willoch, F.; Schoultz, B.W.; Benyhe, S.; Ötvös, F. Synthesis and In Silico Profile Modeling of 6-O-Fluoroalkyl-6-O-desmethyl-diprenorphine Analogs. Int. J. Mol. Sci. 2025, 26, 9427. https://doi.org/10.3390/ijms26199427

AMA Style

Marton J, Gombos D, Cumming P, Fehér T, Milentyev A, Bauer B, Willoch F, Schoultz BW, Benyhe S, Ötvös F. Synthesis and In Silico Profile Modeling of 6-O-Fluoroalkyl-6-O-desmethyl-diprenorphine Analogs. International Journal of Molecular Sciences. 2025; 26(19):9427. https://doi.org/10.3390/ijms26199427

Chicago/Turabian Style

Marton, János, Dávid Gombos, Paul Cumming, Tamás Fehér, Alexander Milentyev, Beate Bauer, Frode Willoch, Bent Wilhelm Schoultz, Sándor Benyhe, and Ferenc Ötvös. 2025. "Synthesis and In Silico Profile Modeling of 6-O-Fluoroalkyl-6-O-desmethyl-diprenorphine Analogs" International Journal of Molecular Sciences 26, no. 19: 9427. https://doi.org/10.3390/ijms26199427

APA Style

Marton, J., Gombos, D., Cumming, P., Fehér, T., Milentyev, A., Bauer, B., Willoch, F., Schoultz, B. W., Benyhe, S., & Ötvös, F. (2025). Synthesis and In Silico Profile Modeling of 6-O-Fluoroalkyl-6-O-desmethyl-diprenorphine Analogs. International Journal of Molecular Sciences, 26(19), 9427. https://doi.org/10.3390/ijms26199427

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