Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor
<i>N</i>-Nitroso-3-morpholinosydnonimine <b>3</b> was prepared by nitrosation of SIN-1 and characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agree...
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MDPI AG
2024-09-01
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| author | Nathalie Saffon-Merceron Christian Lherbet Pascal Hoffmann |
| author_facet | Nathalie Saffon-Merceron Christian Lherbet Pascal Hoffmann |
| author_sort | Nathalie Saffon-Merceron |
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| description | <i>N</i>-Nitroso-3-morpholinosydnonimine <b>3</b> was prepared by nitrosation of SIN-1 and characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which releases both nitric oxide and superoxide radical, decomposition of this nitrosylated sydonimine could yield nitric oxide as the only decomposition product, and thus without the formation of toxic peroxynitrite. |
| format | Article |
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| institution | DOAJ |
| issn | 1422-8599 |
| language | English |
| publishDate | 2024-09-01 |
| publisher | MDPI AG |
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| spelling | doaj-art-8a9c8a451d004b81b75544cbed6df8fa2025-08-20T02:43:20ZengMDPI AGMolbank1422-85992024-09-0120244M188610.3390/M1886Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical DonorNathalie Saffon-Merceron0Christian Lherbet1Pascal Hoffmann2Institut de Chimie de Toulouse, Université Toulouse 3 Paul Sabatier, ICT-UAR CNRS 2599, 118 Route de Narbonne, CEDEX 9, 31062 Toulouse, FranceLaboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique LSPCMIB, Université Toulouse 3 Paul Sabatier, UMR CNRS UPS 5068, 118 Route de Narbonne, CEDEX 9, 31062 Toulouse, FranceLaboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique LSPCMIB, Université Toulouse 3 Paul Sabatier, UMR CNRS UPS 5068, 118 Route de Narbonne, CEDEX 9, 31062 Toulouse, France<i>N</i>-Nitroso-3-morpholinosydnonimine <b>3</b> was prepared by nitrosation of SIN-1 and characterized by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which releases both nitric oxide and superoxide radical, decomposition of this nitrosylated sydonimine could yield nitric oxide as the only decomposition product, and thus without the formation of toxic peroxynitrite.https://www.mdpi.com/1422-8599/2024/4/M1886sydnonesydnonimineiminenitric oxideSIN-1 |
| spellingShingle | Nathalie Saffon-Merceron Christian Lherbet Pascal Hoffmann Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor Molbank sydnone sydnonimine imine nitric oxide SIN-1 |
| title | Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor |
| title_full | Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor |
| title_fullStr | Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor |
| title_full_unstemmed | Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor |
| title_short | Synthesis and Characterization of <i>N</i>-Nitroso-3-morpholinosydnonimine as NO Radical Donor |
| title_sort | synthesis and characterization of i n i nitroso 3 morpholinosydnonimine as no radical donor |
| topic | sydnone sydnonimine imine nitric oxide SIN-1 |
| url | https://www.mdpi.com/1422-8599/2024/4/M1886 |
| work_keys_str_mv | AT nathaliesaffonmerceron synthesisandcharacterizationofininitroso3morpholinosydnonimineasnoradicaldonor AT christianlherbet synthesisandcharacterizationofininitroso3morpholinosydnonimineasnoradicaldonor AT pascalhoffmann synthesisandcharacterizationofininitroso3morpholinosydnonimineasnoradicaldonor |