Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities

Bioorganic & Medicinal Chemistry - Tập 23 - Trang 5452-5458 - 2015
Christoph Reiter1, Tony Fröhlich1, Lisa Gruber2, Corina Hutterer3, Manfred Marschall3, Cornelia Voigtländer4,5, Oliver Friedrich4,5, Barbara Kappes4,5, Thomas Efferth2, Svetlana B. Tsogoeva1
1Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nuremberg, Henkestraße 42, 91054 Erlangen, Germany
2Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, 55128 Mainz, Germany
3Institute for Clinical and Molecular Virology, University of Erlangen-Nuremberg, Schlossgarten 4, 91054 Erlangen, Germany
4Institute of Medical Biotechnology, University of Erlangen-Nuremberg, Paul-Gordon-Straße 3, 91052 Erlangen, Germany
5Erlangen Graduate School of Advanced Optical Technologies (SAOT), Paul-Gordon-Straße 6, 91058 Erlangen, Germany

Tài liệu tham khảo

Jung, 2004, Curr. Med. Chem., 11, 1265, 10.2174/0929867043365233 Singh, 2004, Anticancer Res., 24, 2277 Efferth, 2005, Drug Resist. Updates, 8, 85, 10.1016/j.drup.2005.04.003 Efferth, 2006, Planta Med., 73, 299, 10.1055/s-2007-967138 Cabello, 2012, Invest. New Drugs, 30, 1289, 10.1007/s10637-011-9676-7 Klayman, 1985, Science, 228, 1049, 10.1126/science.3887571 Li, 2003, Curr. Med. Chem., 10, 2197, 10.2174/0929867033456710 Meunier, 2010, Acc. Chem. Res., 43, 1444, 10.1021/ar100070k Kumar, 2011, Curr. Med. Chem., 18, 3889, 10.2174/092986711803414340 Qian, 1982, J. Tradit. Chin. Med., 2, 271 Romero, 2005, Antiviral Res., 68, 75, 10.1016/j.antiviral.2005.07.005 Efferth, 2008, Clin. Infect. Dis., 47, 804, 10.1086/591195 Wohlfarth, 2009, Acta Pharmacol. Sin., 30, 25, 10.1038/aps.2008.5 Cumming, 1997, Adv. Pharmacol., 37, 253, 10.1016/S1054-3589(08)60952-7 Efferth, 2004, Free Radical Biol. Med., 37, 998, 10.1016/j.freeradbiomed.2004.06.023 Wondrak, 2009, Antioxid. Redox Signal., 11, 3013, 10.1089/ars.2009.2541 Eichhorn, 2013, Biochem. Pharmacol., 85, 38, 10.1016/j.bcp.2012.10.006 Kaptein, 2006, Antiviral Res., 69, 60, 10.1016/j.antiviral.2005.10.003 Mehta, 2002, Chem. Soc. Rev., 31, 324, 10.1039/b204748a Tietze, 2003, Angew. Chem., Int. Ed., 42, 3996, 10.1002/anie.200200553 Ganesan, 2004, Curr. Opin. Biotechnol., 15, 584, 10.1016/j.copbio.2004.09.002 Gademann, 2006, Chimia, 60, 841, 10.2533/chimia.2006.841 Alagbala, 2006, J. Med. Chem., 49, 7836, 10.1021/jm060803i Meunier, 2008, Acc. Chem. Res., 41, 69, 10.1021/ar7000843 Tsogoeva, 2010, Mini Rev. Med. Chem., 10, 773, 10.2174/138955710791608280 Horwedel, 2010, J. Med. Chem., 53, 4842, 10.1021/jm100404t Wang, 2013, Bioorg. Med. Chem. Lett., 23, 4424, 10.1016/j.bmcl.2013.05.057 Conyers, 2014, Bioorg. Med. Chem. Lett., 24, 1285, 10.1016/j.bmcl.2014.01.059 Mazzone, 2014, Bioorg. Med. Chem. Lett., 24, 2440, 10.1016/j.bmcl.2014.04.025 Reiter, 2015, Eur. J. Med. Chem., 97, 164, 10.1016/j.ejmech.2015.04.053 Posner, 2007, J. Med. Chem., 50, 2516, 10.1021/jm070149m Posner, 2008, J. Med. Chem., 51, 1035, 10.1021/jm701168h Woodard, 2009, J. Med. Chem., 52, 7458, 10.1021/jm9005934 Rosenthal, 2009, J. Med. Chem., 52, 1198, 10.1021/jm801484v Kyu Moon, 2011, Bioorg. Med. Chem. Lett., 21, 2773, 10.1016/j.bmcl.2010.09.123 Mott, 2013, J. Med. Chem., 56, 2630, 10.1021/jm400058j Haynes, 2007, Chem. Med. Chem., 2, 1448, 10.1002/cmdc.200700064 Reiter, 2012, Bioorg. Med. Chem., 20, 5637, 10.1016/j.bmc.2012.07.015 Reiter, 2014, Eur. J. Med. Chem., 75, 403, 10.1016/j.ejmech.2014.01.043 Stocks, 2007, Angew. Chem. Int. Ed., 46, 6278, 10.1002/anie.200604697 Hu, 2001, J. Labelled Compd. Radiopharm., 44, 987, 10.1002/jlcr.511 Posner, 2003, J. Med. Chem., 46, 1060, 10.1021/jm020461q Chadwick, 2009, Bioorg. Med. Chem., 17, 1325, 10.1016/j.bmc.2008.12.017 Kim, 2004, J. Org. Chem., 69, 3242, 10.1021/jo0498765 Posner, 2004, J. Med. Chem., 47, 1299, 10.1021/jm0303711 Marschall, 2000, Antimicrob. Agents Chemother., 44, 1588, 10.1128/AAC.44.6.1588-1597.2000 Chou, 2011, Antiviral Res., 92, 364, 10.1016/j.antiviral.2011.07.018 Kimmig, 1990, Cancer Res., 50, 6793 Gillet, 2004, Cancer Res., 64, 8987, 10.1158/0008-5472.CAN-04-1978 Efferth, 2008, Clin. Cancer Res., 14, 2405, 10.1158/1078-0432.CCR-07-4525 Lambros, 1979, J. Parasitol., 65, 418, 10.2307/3280287 Smilkstein, 2004, Antimicrob. Agents Chemother., 48, 1803, 10.1128/AAC.48.5.1803-1806.2004 Beez, 2011, Antimicrob. Agents Chemother., 55, 50, 10.1128/AAC.00916-10