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Lett."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"3201","DOI":"10.1021\/jm201657x","volume":"55","author":"Lin Y.-S.","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"5583","DOI":"10.1016\/j.bmc.2012.07.019","volume":"20","author":"De Schutter J. W.","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"5261","DOI":"10.1016\/j.tetlet.2007.05.136","volume":"48","author":"Hesse S.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1021\/jm010081p","volume":"45","author":"Tranberg C. E.","year":"2002","journal-title":"J. Med. Chem."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1016\/j.nbd.2009.05.005","volume":"35","author":"Eckert G. P.","year":"2009","journal-title":"Neurobiol. 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C.","year":"1975","journal-title":"Biochemistry"},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1089\/adt.2007.057","volume":"5","author":"Glickman J. F.","year":"2007","journal-title":"Assay Drug Dev. Technol."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"2187","DOI":"10.1021\/jm7015733","volume":"51","author":"Dunford J. E.","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref54\/cit54","unstructured":"Amstutz, R.; Bold, G.; Cotesta, S.; Jahnke, W.; Marzinzik, A.; Mueller-Hartwieg, C.; Ofner, S.; Stauffer, F.; Zimmermann, J.Quinolines as Inhibitors of Farnesyl Pyrophosphate Synthase. WO 2009\/106586 A1, 2009."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"1429","DOI":"10.1021\/cb300189b","volume":"7","author":"Owen S. C.","year":"2012","journal-title":"ACS Chem. Biol."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.jconrel.2013.01.032","volume":"167","author":"Giger E. V.","year":"2013","journal-title":"J. Controlled Release"},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"m166","DOI":"10.1107\/S0108270110017634","volume":"66","author":"Freire E.","year":"2010","journal-title":"Acta Crystallogr., Sect. C: Cryst. Struct. Commun."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.poly.2008.10.030","volume":"28","author":"Kunnas-Hiltunen S.","year":"2009","journal-title":"Polyhedron"},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"1840","DOI":"10.1016\/j.bmcl.2008.02.009","volume":"18","author":"Peukert S.","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"742","DOI":"10.1111\/cbdd.12121","volume":"81","author":"Lindert S.","year":"2013","journal-title":"Chem. Biol. Drug Des."},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"660","DOI":"10.1038\/nchembio.421","volume":"6","author":"Jahnke W.","year":"2010","journal-title":"Nature Chem. Biol."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1002\/cmdc.201000016","volume":"5","author":"Jahnke W.","year":"2010","journal-title":"ChemMedChem"},{"key":"ref63\/cit63","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1186\/1472-6807-12-32","volume":"12","author":"Park J.","year":"2012","journal-title":"BMC Struct. Biol."},{"key":"ref64\/cit64","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1016\/j.bbrc.2011.03.070","volume":"407","author":"R\u00e4ikk\u00f6nen J.","year":"2011","journal-title":"Biochem. Biophys Res. 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