The Synthesis of Novel Isoindoline Nitroxides Bearing Water-Solubilising Functionality
A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the correspo...
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| Published in | European Journal of Organic Chemistry Vol. 2009; no. 12; pp. 1902 - 1915 |
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| Main Authors | , , |
| Format | Book Review Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.04.2009
WILEY‐VCH Verlag Wiley Wiley-VCH |
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| Abstract | A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the corresponding tetraethylisoindoline system. Instead, various tetraethylisoindoline analogues were accessed by the oxidation of methyl groups attached to the aromatic ring to give the carboxylic acids. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
A number of novel tetramethyl‐ and tetraethylisoindoline nitroxides possessing water‐solubilising functionalities were synthesised. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants. |
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| AbstractList | A range of novel tetramethyl- and tetraethylisoindoline nitroxides, possessing aryl-linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the corresponding tetraethylisoindoline system. Instead, various tetraethylisoindoline analogues were accessed by the oxidation of methyl groups attached to the aromatic ring to give the carboxylic acids. The increased steric bulk of the tetraethyl structures should limit bio-reduction and these compounds may have potential as antioxidants. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the corresponding tetraethylisoindoline system. Instead, various tetraethylisoindoline analogues were accessed by the oxidation of methyl groups attached to the aromatic ring to give the carboxylic acids. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) A number of novel tetramethyl‐ and tetraethylisoindoline nitroxides possessing water‐solubilising functionalities were synthesised. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants. Abstract A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were prepared. Notably, the chemistry established for the aromatic dibromination of the tetramethylisoindolines was not easily transferred to the corresponding tetraethylisoindoline system. Instead, various tetraethylisoindoline analogues were accessed by the oxidation of methyl groups attached to the aromatic ring to give the carboxylic acids. The increased steric bulk of the tetraethyl structures should limit bio‐reduction and these compounds may have potential as antioxidants.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) |
| Author | Fairfull-Smith, Kathryn E. Brackmann, Farina Bottle, Steven E. |
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| Cites_doi | 10.1055/s-2008-1078445 10.1016/j.fct.2007.08.028 10.1039/b504354a 10.1016/j.freeradbiomed.2004.08.006 10.1002/ejoc.200800597 10.1039/b002497j 10.1039/b806963h 10.1007/BF03166117 10.1016/j.freeradbiomed.2004.06.035 10.1093/hmg/ddh189 10.1002/chem.200700079 10.1039/b307652k 10.1016/j.tet.2007.03.170 10.1021/tx800183t 10.1021/ja01637a068 10.1016/S0891-5849(00)00176-3 10.1021/jo00213a028 10.1002/prac.19640230111 10.1016/0076-6879(94)34130-3 10.1523/JNEUROSCI.23-36-11453.2003 10.1002/tcr.20033 10.1002/1521-3773(20001215)39:24<4494::AID-ANIE4494>3.0.CO;2-X 10.1021/jm9802160 10.1039/p19800001834 10.1071/CH9830397 10.1016/S0040-4039(00)87091-4 10.1016/S0891-5849(02)01238-8 10.1021/ma00231a042 10.1039/b001891k 10.1039/a806884d 10.1016/S0223-5234(01)01247-8 |
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| Keywords | Medicinal chemistry Isoindoline ANTIOXIDANTS TEMPOL NITRIC-OXIDE Nitroxide Antioxidant Radicals FREE-RADICALS Water Nitroxyl Molecular structure Nitrogen heterocycle Alcohol Steric hindrance Isoindole derivatives Chemical reduction Amine Carboxylic acid Steric effect Organic free radical Analog Aromatic compound Oxidation Phosphonic acid derivatives Chemical synthesis |
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| Snippet | A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were... A range of novel tetramethyl- and tetraethylisoindoline nitroxides, possessing aryl-linked carboxylic acids, amines, alcohols and phosphonic acids were... Abstract A range of novel tetramethyl‐ and tetraethylisoindolinenitroxides, possessing aryl‐linked carboxylic acids, amines, alcohols and phosphonic acids were... |
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| StartPage | 1902 |
| SubjectTerms | Antioxidant Chemistry Chemistry, Organic Exact sciences and technology Free radicals chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Isoindoline Medicinal chemistry Nitroxide Organic chemistry Physical Sciences Preparations and properties Radicals Reactivity and mechanisms Science & Technology |
| Title | The Synthesis of Novel Isoindoline Nitroxides Bearing Water-Solubilising Functionality |
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