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Synthesis 2001(5): 0768-0772
DOI: 10.1055/s-2001-12764
DOI: 10.1055/s-2001-12764
PAPER
© Georg Thieme Verlag Stuttgart · New York
2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants
Further Information
Received
18 September 2000
Publication Date:
28 September 2004 (online)
Publication History
Publication Date:
28 September 2004 (online)
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Abstract
The coupling of arylboronic acids with 2,6-diamino-3,5-dibromo-1,4-pyrazine (6) gave 2,6-diamino-3,5-diaryl-1,4-pyrazines (7). The reaction of 7 with methyl glyoxal in aqueous EtOH-HCl led to the N,N"-disubstituted products 8, instead of the expected bicyclic imidazolopyrazinones 1. The 2,6-bis[1-(ethoxycarbonyl)-ethylamino]-3,5-diaryl-1,4-pyrazines 8 are powerful inhibitors of the AAPH-induced linoleate peroxidation.
Key words
2,6-diamino-3,5-diaryl-1,4-pyrazine - imidazolopyrazinone - antioxidant - coelenterazine analogs
-
1a
Dubuisson M,Trouet A, andRees J.-F. inventors; Belg. Patent WO 98/43641. -
1b
Marchand-Brynaert J,de Tollenaere C,Cavalier J.-F,Burton M, andRees J.-F. inventors; Eur. Patent, submitted 00 87 0107.0. -
1c
Rees J.-F.de Wergifosse B.Noiset O.Dubuisson M.Janssens B.Thompson EM. J. Exp. Biol. 1998, 201: 1211 -
1d
Dubuisson M.de Wergifosse B.Trouet A.Baguet F.Marchand-Brynaert J.Rees J.-F. Biochem. Pharmacol. 2000, 60: 471 - 2
Devillers I.de Wergifosse B.Bruneau M.-P.Tinant B.Declercq J.-P.Touillaux R.Rees J.-F.Marchand-Brynaert J. J. Chem. Soc., Perkin Trans. 2 1999, 1481 -
3a
de Wergifosse B.Noiset O.Dubuisson M.Marchand-Brynaert J.Baguet F.Rees J.-F. In Bioluminescence and ChemiluminescenceRoda A.Kricka L.Stanley P. Eds.; Wiley and Son; NY: 1999. p.396 -
3b
Ohmiya Y.Hirano T. Chem. Biol. 1996, 3: 337 -
3c
Jones K.Hibbert F.Keenan M. Trends Biotechnol. 1999, 17: 477 -
4a
Hirano T.Nishibuchi S.Yoneda M.Tsujimoto K.Ohashi M. Tetrahedron 1993, 49: 9267 -
4b
Keenan M.Jones K.Hibbert F. Chem. Commun. 1997, 323 -
4c
Gonzales-Trueba G.Paradisi C.Zoratti M. Anal. Biochem. 1996, 240: 308 - 5
Kishi Y.Tinano H.Goto T. Tetrahedron Lett. 1972, 27: 2747 - 6
Jones K.Keenan M.Hibbert F. Synlett 1996, 509 - 7
Barot NR.Elvidge JA. J. Chem. Soc., Perkin Trans. 1 1973, 606 - 8
Shaw JT.Brotherton CE.Moon RW. J. Heterocycl. Chem. 1980, 17: 11 - 9
Tong YC. J. Heterocl. Chem. 1975, 12: 1127 -
10a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
10b
Suzuki A. J. Organomet. Chem. 1999, 576: 147 -
11a
Gong Y.Pauls HW. Synlett 2000, 829 -
11b
Nakamura H.Aizawa M.Takeuchi D.Murai A.Shimoura O. Tetrahedron Lett. 2000, 41: 2185 - 12
Feutrill GI.Mirrington RN. Aust. J. Chem. 1972, 25: 1731 - 13
Sato N. J. Heterocycl. Chem. 1982, 673 - 14
Teranishi K.Goto T. Bull. Chem. Soc. Jpn. 1990, 63: 3132 - 15
Teranishi K.Shimomura O. Anal. Biochem. 1997, 249: 37 - 16
Bowry VW.Ingold KU. Acc. Chem. Res. 1999, 32: 27 - 17
de Heer MI.Korth H.-G.Mulder P. J. Org. Chem. 1999, 64: 6969 - 18
Barclay LRC.Edwards CE.Vinqvist MR. J. Am. Chem. Soc. 1999, 121: 6226 - 19
Zhou B.Jia Z.-S.Chen Z.-H.Yang L.Wu L.-M.Liu Z.-L. J. Chem. Soc., Perkin Trans. 2 2000, 785