- COELENTERAZINE ANALOGUES AND COELENTERAMIDE ANALOGUES
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Coelenterazine analogs with different luminescence properties from conventional ones and coelenteramide analogs with different fluorescence properties from conventional ones have been desired. The invention provides coelenterazine analogs modified at the
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- N-(alkyl)-2-amino-1,4-pyrazine derivatives: Synthesis and antioxidative properties of 3- and 3,5-p-hydroxyphenyl-substituted compounds
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2-Amino-5-(p-hydroxyphenyl)-1,4-pyrazine and 2-amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine are endowed with excellent antioxidative properties. For a possible development in medicinal chemistry, the lipophilicity of these lead compounds has to be increased. Therefore various methods of N-alkylation were systematically explored. The best results were obtained by quenching aminopyrazinyl anion with alkyl iodides, and by coupling aldehydes (reductive amination) in the presence of phenylsilane and tin catalyst. Aminopyrazines equipped with linear alkyl side-chains of at least six carbons showed improved radical-scavenging properties in lipidic media.
- Jeanjot, Paul,Bruyneel, Fre?de?ric,Arrault, Axelle,Gharbi, Sonia,Cavalier, Jean-Franc?ois,Abels, Agne?s,Marchand, Ce?cile,Touillaux, Roland,Rees, Jean-Franc?ois,Marchand-Brynaert, Jacqueline
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p. 513 - 522
(2007/10/03)
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- Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties
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A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules.
- Adamczyk, Maciej,Akireddy, Srinivasa Rao,Johnson, Donald D.,Mattingly, Phillip G.,Pan, You,Reddy, Rajarathnam E.
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p. 8129 - 8142
(2007/10/03)
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