Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores

Main Article Content

Ivana I. Jevtić
http://orcid.org/0000-0002-7653-2420
Jelena P. Penjišević
http://orcid.org/0000-0002-3374-1193
Milovan D. Ivanović
Slađana V. Kostić-Rajačić
http://orcid.org/0000-0003-0777-3076

Abstract

A scalable, cost-efficient and simple synthetic pathway towards pot­ential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmaco­phores linked by the four methylene group chain were synthesized in 33, 35 and 39 % overall yield after a four-step synthetic route starting from three commercially available N-aryl piperazines. The anilino piperidine precursor was easily prepared in three steps, as previously published, starting from 4-piperidone. The synthesis presented in this paper could be of interest for het­ero­cyclic and general organic chemistry. The newly designed compounds pos­sessing two pharmacophores, opioid and D2/D3, are potentially useful pharma­cological probes. Of particular interest would be the simultaneous binding to both opioid and D2/D3 receptors, and the resulting pharmacological responses may be useful for the further understanding of tolerance and dependence phen­omena in opioid clinical use and/or abuse.

Article Details

How to Cite
[1]
I. I. Jevtić, J. P. Penjišević, M. D. Ivanović, and S. V. Kostić-Rajačić, “Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores”, J. Serb. Chem. Soc., vol. 84, no. 7, pp. 639–647, Jul. 2019.
Section
Organic Chemistry
Author Biographies

Ivana I. Jevtić, Institute of Chemistry, Technology and Metallurgy National Institute, University of Belgrade

Junior Researcher,Department of Chemistry

Jelena P. Penjišević, Institute of Chemistry, Technology and Metallurgy National Institute, University of Belgrade

Assistant Research Professor,

Department of Chemistry

Milovan D. Ivanović, Faculty of Chemistry, University of Belgrade

Associate Professor, 

Department of organic chemistry

Slađana V. Kostić-Rajačić, Institute of Chemistry, Technology and Metallurgy National Institute, University of Belgrade

Full Research Professor,

Department of Chemistry

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