Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor

Tetrahedron - Tập 66 - Trang 8544-8550 - 2010
Ana M.G. Silva1, Andreia Leite1, Mariana Andrade1, Paula Gameiro1, Paula Brandão2, Vítor Felix2, Baltazar de Castro1, Maria Rangel3
1Requimte, Departamento de Química, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal
2Department of Chemistry, CICECO, University of Aveiro, 3810-193 Aveiro, Portugal
3Requimte, Instituto de Ciências Biomédicas Abel Salazar, 4099-003 Porto, Portugal

Tài liệu tham khảo

Lakowicz, 2006 de Silva, 1997, Chem. Rev., 97, 1515, 10.1021/cr960386p Amendola, 1999, Coord. Chem. Rev., 190–192, 649, 10.1016/S0010-8545(99)00110-1 Ljosa, 2008, Trends Biotechnol., 26, 527, 10.1016/j.tibtech.2008.06.008 Leopoldo, 2009, Drug Discovery Today, 14, 706, 10.1016/j.drudis.2009.03.015 Examples of fluorescence detection of metal ions: Domaille, 2008, Nat. Chem. Biol., 4, 168, 10.1038/nchembio.69 Vinkenborg, 2010, Curr. Opin. Chem. Biol., 14, 231, 10.1016/j.cbpa.2009.11.022 Burgess, 2008, Vol. 60, 167 Liu, 2002, Med. Res. Rev., 22, 26, 10.1002/med.1027 Zhou, 2006, J. Med. Chem., 49, 4171, 10.1021/jm0600949 Zhou, 2008, Biomacromolecules, 9, 1372, 10.1021/bm701122u Crisponi, 2008, Coord. Chem. Rev., 252, 1225, 10.1016/j.ccr.2007.12.014 Santos, 2008, Coord. Chem. Rev., 252, 1213, 10.1016/j.ccr.2008.01.033 Sakurai, 2006, Bull. Chem. Soc. Jpn., 79, 1645, 10.1246/bcsj.79.1645 Examples of (3,4-HPO)s fluorescent probes: Ma, 2004, J. Med. Chem., 47, 6349, 10.1021/jm049751s Fakih, 2008, J. Med. Chem., 51, 4539, 10.1021/jm8001247 Katoh, 2005, Heterocycles, 65, 2195, 10.3987/COM-05-10471 Examples of naphthalene-based fluorescent sensors: Senthilnithy, 2008, Luminescence, 24, 203, 10.1002/bio.1083 Yang, 2006, Tetrahedron Lett., 47, 2911, 10.1016/j.tetlet.2006.02.126 Al-Rasbi, 2006, Dalton Trans., 4769, 10.1039/B609809F Tumambac, 2004, Tetrahedron, 60, 11293, 10.1016/j.tet.2004.07.053 De Costa, 2004, J. Photochem. Photobiol., A, 162 Otón, 2004, Chem. Commun., 1658, 10.1039/B404601C Kubo, 2000, Chem. Commun., 653, 10.1039/b000352m Gonçalves, 2009, Chem. Rev., 109, 190, 10.1021/cr0783840 Lee, 2002, Eur. J. Med. Chem., 37, 333, 10.1016/S0223-5234(02)01354-5 Petrillo, 2007, Invest. New Drugs, 25, 535, 10.1007/s10637-007-9065-4 Patrick, 2009, Eur. J. Med. Chem., 44, 3543, 10.1016/j.ejmech.2009.03.014 Examples of microwave-assisted synthesis of organic dyes: Lee, 2010, Chem. Commun., 46, 1068, 10.1039/b924350j Mijin, 2010, Dyes Pigm., 85, 73, 10.1016/j.dyepig.2009.10.006 Nourmohammadian, 2010, Synth. Commun., 40, 901, 10.1080/00397910903026699 Abdel-Hamid, 2009, Tetrahedron Lett., 50, 6947, 10.1016/j.tetlet.2009.09.098 Thirumurugan, 2009, Dyes Pigm., 81, 245, 10.1016/j.dyepig.2008.10.018 Glasnov, 2007, QSAR Comb. Sci., 26, 1261, 10.1002/qsar.200740122 March, 1992 Beak, 1976, J. Am. Chem. Soc., 98, 171, 10.1021/ja00417a027 Schlegel, 1982, J. Am. Chem. Soc., 104, 5347, 10.1021/ja00384a017 El-Jammal, 1994, J. Med. Chem., 37, 461, 10.1021/jm00030a005 NMR tubes in acetonitrile-d3 and methanol-d4 were prepared from a saturated solution of ligand L1 in DMSO-d6. Santos, 2002, J. Inorg. Biochem., 92, 43, 10.1016/S0162-0134(02)00483-X Sheldrick, 1997 Sheldrick, 1990, Acta Crystallogr., Sect. A, 46, 467, 10.1107/S0108767390000277 Spek, 2008