Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions

An efficient synthesis of a highly potent and selective IP (PGI(2) receptor) agonist that is not structurally analogous to PGI(2) is described. This synthesis is accomplished through the following key steps: Nucleophilic ring-opening of 3-(4-chlorophenyl)-oxazolidin-2-one prepared by a one-pot proce...

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Autores principales: Morita, Yasuhiro, Ishigaki, Takeshi, Kawamura, Kuniaki, Hayashi, Ryoji, Isogaya, Masafumi, Kitsukawa, Mika, Miyamoto, Mitsuko, Uchida, Masashi, Iseki, Katsuhiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268181/
https://www.ncbi.nlm.nih.gov/pubmed/22293844
http://dx.doi.org/10.3390/molecules17021233
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author Morita, Yasuhiro
Ishigaki, Takeshi
Kawamura, Kuniaki
Hayashi, Ryoji
Isogaya, Masafumi
Kitsukawa, Mika
Miyamoto, Mitsuko
Uchida, Masashi
Iseki, Katsuhiko
author_facet Morita, Yasuhiro
Ishigaki, Takeshi
Kawamura, Kuniaki
Hayashi, Ryoji
Isogaya, Masafumi
Kitsukawa, Mika
Miyamoto, Mitsuko
Uchida, Masashi
Iseki, Katsuhiko
author_sort Morita, Yasuhiro
collection PubMed
description An efficient synthesis of a highly potent and selective IP (PGI(2) receptor) agonist that is not structurally analogous to PGI(2) is described. This synthesis is accomplished through the following key steps: Nucleophilic ring-opening of 3-(4-chlorophenyl)-oxazolidin-2-one prepared by a one-pot procedure with 4-piperidinol and selective O-alkylation of 1-(2-(4-chlorophenylamino)ethyl)piperidin-4-ol. The obtained compound is a potent and selective IP agonist displaying a long duration of action.
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spelling pubmed-62681812018-12-10 Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions Morita, Yasuhiro Ishigaki, Takeshi Kawamura, Kuniaki Hayashi, Ryoji Isogaya, Masafumi Kitsukawa, Mika Miyamoto, Mitsuko Uchida, Masashi Iseki, Katsuhiko Molecules Article An efficient synthesis of a highly potent and selective IP (PGI(2) receptor) agonist that is not structurally analogous to PGI(2) is described. This synthesis is accomplished through the following key steps: Nucleophilic ring-opening of 3-(4-chlorophenyl)-oxazolidin-2-one prepared by a one-pot procedure with 4-piperidinol and selective O-alkylation of 1-(2-(4-chlorophenylamino)ethyl)piperidin-4-ol. The obtained compound is a potent and selective IP agonist displaying a long duration of action. MDPI 2012-01-31 /pmc/articles/PMC6268181/ /pubmed/22293844 http://dx.doi.org/10.3390/molecules17021233 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Morita, Yasuhiro
Ishigaki, Takeshi
Kawamura, Kuniaki
Hayashi, Ryoji
Isogaya, Masafumi
Kitsukawa, Mika
Miyamoto, Mitsuko
Uchida, Masashi
Iseki, Katsuhiko
Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title_full Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title_fullStr Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title_full_unstemmed Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title_short Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions
title_sort synthesis of novel ip agonists via n-aminoethyl cyclic amines prepared by decarboxylative ring-opening reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268181/
https://www.ncbi.nlm.nih.gov/pubmed/22293844
http://dx.doi.org/10.3390/molecules17021233
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