Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores
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 % ove...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Serbian Chemical Society
2019-01-01
|
| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2019/0352-51391800105J.pdf |
| _version_ | 1818755466811932672 |
|---|---|
| author | Jevtić Ivana I. Penjišević Jelena Z. Ivanović Milovan D. Kostić-Rajačić Slađana V. |
| author_facet | Jevtić Ivana I. Penjišević Jelena Z. Ivanović Milovan D. Kostić-Rajačić Slađana V. |
| author_sort | Jevtić Ivana I. |
| collection | DOAJ |
| description | 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. [Project of the Serbian Ministry of Education, Science and Technological
Development, Grant no. 172032] |
| first_indexed | 2024-12-18T05:39:36Z |
| format | Article |
| id | doaj.art-1bc32f98f1f44fa199620f2d1c4f97b2 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-18T05:39:36Z |
| publishDate | 2019-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-1bc32f98f1f44fa199620f2d1c4f97b22022-12-21T21:19:12ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212019-01-0184763964710.2298/JSC181002105J0352-51391800105JSynthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophoresJevtić Ivana I.0Penjišević Jelena Z.1Ivanović Milovan D.2Kostić-Rajačić Slađana V.3ICTM, Department of Chemistry, University of Belgrade, Belgrade, SerbiaICTM, Department of Chemistry, University of Belgrade, Belgrade, SerbiaFaculty of Chemistry, University of Belgrade, Belgrade, SerbiaICTM, Department of Chemistry, University of Belgrade, Belgrade, SerbiaA 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. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172032]http://www.doiserbia.nb.rs/img/doi/0352-5139/2019/0352-51391800105J.pdfpiperidinepiperazineheterocyclesN-alkylationanalgesicsdopaminergic |
| spellingShingle | Jevtić Ivana I. Penjišević Jelena Z. Ivanović Milovan D. Kostić-Rajačić Slađana V. Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores Journal of the Serbian Chemical Society piperidine piperazine heterocycles N-alkylation analgesics dopaminergic |
| title | Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores |
| title_full | Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores |
| title_fullStr | Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores |
| title_full_unstemmed | Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores |
| title_short | Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores |
| title_sort | synthetic route towards potential bivalent ligands possessing opioid and d2 d3 pharmacophores |
| topic | piperidine piperazine heterocycles N-alkylation analgesics dopaminergic |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2019/0352-51391800105J.pdf |
| work_keys_str_mv | AT jevticivanai syntheticroutetowardspotentialbivalentligandspossessingopioidandd2d3pharmacophores AT penjisevicjelenaz syntheticroutetowardspotentialbivalentligandspossessingopioidandd2d3pharmacophores AT ivanovicmilovand syntheticroutetowardspotentialbivalentligandspossessingopioidandd2d3pharmacophores AT kosticrajacicslađanav syntheticroutetowardspotentialbivalentligandspossessingopioidandd2d3pharmacophores |