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Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl

Authorized Users Only
2017
Authors
Jevtić, Ivana
Došen-Mićović, Ljiljana
Ivanović, Evica
Todorović, Nina
Ivanović, Milovan D.
Article (Published version)
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Abstract
The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
Keywords:
heterocycles / rearrangement / acylation / protecting groups / diastereoselectivity
Source:
Synthesis, 2017, 49, 14, 3126-3136
Publisher:
  • Georg Thieme Verlag Kg, Stuttgart
Funding / projects:
  • Structure-activity relationship of newly synthesized biological active compound (RS-172032)

DOI: 10.1055/s-0036-1588985

ISSN: 0039-7881

WoS: 000406066800009

Scopus: 2-s2.0-85017147328
[ Google Scholar ]
5
6
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2142
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Jevtić, Ivana
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica
AU  - Todorović, Nina
AU  - Ivanović, Milovan D.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2142
AB  - The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl
VL  - 49
IS  - 14
SP  - 3126
EP  - 3136
DO  - 10.1055/s-0036-1588985
ER  - 
@article{
author = "Jevtić, Ivana and Došen-Mićović, Ljiljana and Ivanović, Evica and Todorović, Nina and Ivanović, Milovan D.",
year = "2017",
abstract = "The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl",
volume = "49",
number = "14",
pages = "3126-3136",
doi = "10.1055/s-0036-1588985"
}
Jevtić, I., Došen-Mićović, L., Ivanović, E., Todorović, N.,& Ivanović, M. D.. (2017). Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl. in Synthesis
Georg Thieme Verlag Kg, Stuttgart., 49(14), 3126-3136.
https://doi.org/10.1055/s-0036-1588985
Jevtić I, Došen-Mićović L, Ivanović E, Todorović N, Ivanović MD. Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl. in Synthesis. 2017;49(14):3126-3136.
doi:10.1055/s-0036-1588985 .
Jevtić, Ivana, Došen-Mićović, Ljiljana, Ivanović, Evica, Todorović, Nina, Ivanović, Milovan D., "Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl" in Synthesis, 49, no. 14 (2017):3126-3136,
https://doi.org/10.1055/s-0036-1588985 . .

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