Synthesis, Chiral Resolution and Enantiomers Absolute Configuration of 4-Nitropropranolol and 7-Nitropropranolol
We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the sam...
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| Published in | Molecules (Basel, Switzerland) Vol. 28; no. 1; p. 57 |
|---|---|
| Main Authors | , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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21.12.2022
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| ISSN | 1420-3049 1420-3049 |
| DOI | 10.3390/molecules28010057 |
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| Abstract | We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the same nitration process, we synthesized 4-nitro- and 7-nitropropranolol as probes to evaluate the possible nitration of the propranolol by the endothelium. The separation of the enantiomers in very high yields and excellent enantiopurity was achieved by chiral HPLC. Finally, we used Riguera’s method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies. |
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| AbstractList | We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the same nitration process, we synthesized 4-nitro- and 7-nitropropranolol as probes to evaluate the possible nitration of the propranolol by the endothelium. The separation of the enantiomers in very high yields and excellent enantiopurity was achieved by chiral HPLC. Finally, we used Riguera’s method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies. We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the same nitration process, we synthesized 4-nitro- and 7-nitropropranolol as probes to evaluate the possible nitration of the propranolol by the endothelium. The separation of the enantiomers in very high yields and excellent enantiopurity was achieved by chiral HPLC. Finally, we used Riguera's method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies.We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the same nitration process, we synthesized 4-nitro- and 7-nitropropranolol as probes to evaluate the possible nitration of the propranolol by the endothelium. The separation of the enantiomers in very high yields and excellent enantiopurity was achieved by chiral HPLC. Finally, we used Riguera's method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies. |
| Audience | Academic |
| Author | Luciano, Paolo Magli, Elisa De Nucci, Gilberto Caliendo, Giuseppe Aiello, Anna Corvino, Angela Severino, Beatrice Fiorino, Ferdinando Casertano, Marcello Perissutti, Elisa Scognamiglio, Antonia Sparaco, Rosa Santagada, Vincenzo Frecentese, Francesco |
| AuthorAffiliation | 1 Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy 2 Department of Public Health, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy 3 Department of Pharmacology, Faculty of Medical Sciences, State University of Campinas (UNICAMP), Campinas 13083-970, SP, Brazil |
| AuthorAffiliation_xml | – name: 2 Department of Public Health, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy – name: 1 Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy – name: 3 Department of Pharmacology, Faculty of Medical Sciences, State University of Campinas (UNICAMP), Campinas 13083-970, SP, Brazil |
| Author_xml | – sequence: 1 givenname: Rosa surname: Sparaco fullname: Sparaco, Rosa – sequence: 2 givenname: Antonia orcidid: 0000-0002-4282-2788 surname: Scognamiglio fullname: Scognamiglio, Antonia – sequence: 3 givenname: Angela orcidid: 0000-0002-0617-156X surname: Corvino fullname: Corvino, Angela – sequence: 4 givenname: Giuseppe surname: Caliendo fullname: Caliendo, Giuseppe – sequence: 5 givenname: Ferdinando orcidid: 0000-0001-7357-5751 surname: Fiorino fullname: Fiorino, Ferdinando – sequence: 6 givenname: Elisa surname: Magli fullname: Magli, Elisa – sequence: 7 givenname: Elisa orcidid: 0000-0002-1754-1191 surname: Perissutti fullname: Perissutti, Elisa – sequence: 8 givenname: Vincenzo surname: Santagada fullname: Santagada, Vincenzo – sequence: 9 givenname: Beatrice orcidid: 0000-0002-3887-8869 surname: Severino fullname: Severino, Beatrice – sequence: 10 givenname: Paolo surname: Luciano fullname: Luciano, Paolo – sequence: 11 givenname: Marcello orcidid: 0000-0001-5037-712X surname: Casertano fullname: Casertano, Marcello – sequence: 12 givenname: Anna surname: Aiello fullname: Aiello, Anna – sequence: 13 givenname: Gilberto surname: De Nucci fullname: De Nucci, Gilberto – sequence: 14 givenname: Francesco orcidid: 0000-0001-8821-2937 surname: Frecentese fullname: Frecentese, Francesco |
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| Cites_doi | 10.1021/cr000665j 10.1263/jbb.100.423 10.1021/ol8008528 10.1016/bs.podrm.2017.02.006 10.1021/jo00413a002 10.1016/S0040-4020(01)81657-4 10.1002/jlcr.2580201002 10.1016/j.ejphar.2021.174544 10.1155/2020/9597426 10.1021/jm00163a036 10.1016/0006-2952(89)90302-X 10.1016/S0957-4166(00)82209-0 10.1128/MMBR.00006-10 10.1016/j.lfs.2021.119425 10.1016/0378-5173(88)90160-3 10.1016/j.lfs.2022.120879 10.1016/S0040-4039(01)80880-7 10.1021/ja00783a034 10.1016/j.jchromb.2021.122668 10.1016/j.chroma.2007.07.005 10.1111/andr.13263 |
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| Copyright | COPYRIGHT 2022 MDPI AG 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2022 by the authors. 2022 |
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| Keywords | 4-nitropropranolol 7-nitropropranolol Riguera’s method NMR absolute configuration assignment chiral HPLC |
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| SubjectTerms | 4-nitropropranolol 7-nitropropranolol Acids Catecholamines chiral HPLC Chromatography, High Pressure Liquid - methods Dopamine Enantiomers Endothelium Magnetic Resonance Spectroscopy Methods Nitration NMR absolute configuration assignment Propranolol Propranolol hydrochloride Riguera’s method Sensors Stereoisomerism |
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| Title | Synthesis, Chiral Resolution and Enantiomers Absolute Configuration of 4-Nitropropranolol and 7-Nitropropranolol |
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