{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,14]],"date-time":"2026-07-14T16:04:00Z","timestamp":1784045040229,"version":"3.55.0"},"reference-count":22,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2022,12,21]],"date-time":"2022-12-21T00:00:00Z","timestamp":1671580800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"State of S\u00e3o Paulo Research Foundation (FAPESP)","award":["2019\/16805-4"],"award-info":[{"award-number":["2019\/16805-4"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2019s method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies.<\/jats:p>","DOI":"10.3390\/molecules28010057","type":"journal-article","created":{"date-parts":[[2022,12,22]],"date-time":"2022-12-22T02:31:11Z","timestamp":1671676271000},"page":"57","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis, Chiral Resolution and Enantiomers Absolute Configuration of 4-Nitropropranolol and 7-Nitropropranolol"],"prefix":"10.3390","volume":"28","author":[{"given":"Rosa","family":"Sparaco","sequence":"first","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4282-2788","authenticated-orcid":false,"given":"Antonia","family":"Scognamiglio","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0617-156X","authenticated-orcid":false,"given":"Angela","family":"Corvino","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giuseppe","family":"Caliendo","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7357-5751","authenticated-orcid":false,"given":"Ferdinando","family":"Fiorino","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisa","family":"Magli","sequence":"additional","affiliation":[{"name":"Department of Public Health, University of Naples Federico II, Via Pansini 5, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1754-1191","authenticated-orcid":false,"given":"Elisa","family":"Perissutti","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincenzo","family":"Santagada","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3887-8869","authenticated-orcid":false,"given":"Beatrice","family":"Severino","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paolo","family":"Luciano","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5037-712X","authenticated-orcid":false,"given":"Marcello","family":"Casertano","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Aiello","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gilberto","family":"De Nucci","sequence":"additional","affiliation":[{"name":"Department of Pharmacology, Faculty of Medical Sciences, State University of Campinas (UNICAMP), Campinas 13083-970, SP, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8821-2937","authenticated-orcid":false,"given":"Francesco","family":"Frecentese","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1016\/bs.podrm.2017.02.006","article-title":"Chapter Six\u2014Propranolol","volume":"Volume 42","author":"Brittain","year":"2017","journal-title":"Profiles of Drug Substances, Excipients and Related Methodology"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"9597426","DOI":"10.1155\/2020\/9597426","article-title":"Facile Synthesis of Propranolol and Novel Derivatives","volume":"2020","author":"Tran","year":"2020","journal-title":"J. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1128\/MMBR.00006-10","article-title":"Nitroaromatic compounds, from synthesis to biodegradation","volume":"74","author":"Ju","year":"2010","journal-title":"Microbiol. Mol. Biol. 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