Effects of substituents on the NMR features of basic bicyclic ring systems of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters

P. C. Appelbaum and P. A. Hunter, The fluoroquinolone antibacterials: past, present and future perspectives, Int. J. Antimicrob. Agents 16 (2000) 5-15; DOI: 10.1016/S0924-8579(00)00192-8.10.1016/S0924-8579(00)00192-8Search in Google Scholar

D. C. Hooper, Quinolone Antimicrobial Agents (Eds. D. C. Hooper and E. Rubinstein), AMS Press, Washington 2003, pp. 3-40.10.1128/9781555817817Search in Google Scholar

S. Emami, A. Shafiee and A. Foroumadi, Structural features of new quinolones and relationship to antibacterial activity against Gram-positive bacteria, Mini Rev. Med. Chem. 6 (2006) 375-386; DOI: 10.2174/138955706776361493.10.2174/138955706776361493Search in Google Scholar

K. E. Brighty and T. D. Gootz, The chemistry and biological profile of trovafloxacin, J. Antimicrob. Chemother. 39 (1997) 1-14; DOI: 10.1093/jac/39.suppl_2.1.10.1093/jac/39.suppl_2.1Search in Google Scholar

M. P. Montanari, M. Prenna, M. Mingoia, S. Ripa and P. E. Varaldo, In vitro antibacterial activity of trovafloxacin and five other fluoroquinolones, Chemotherapy 44 (1998) 85-93; DOI: 10.1159/000007097.10.1159/000007097Search in Google Scholar

J. Vincent, R. Teng, D. K. Dalvie and H. L. Friedman, Pharmacokinetics and metabolism of single oral doses of trovafloxacin, Am. J. Surg. 176 (1998) 8S-13S; DOI: 10.1016/S0002-9610(98)00213-X.10.1016/S0002-9610(98)00213-XSearch in Google Scholar

D. Scuster, C. Laggner and T. Lagner, Why drugs fail - A Study on Side Effects in New Chemical Entities, in Antitargets. Prediction and Prevention of Drug Side Effects (Ed. R. Vaz and T. Klabunde), Wiley WCH Verlag GmbH & Co. KGaA, Weinheim 2008, pp. 3-22.10.1002/9783527621460.ch1Search in Google Scholar

M. J. Liguori, M. G. Anderson, S. Bukofzer, J. McKim, J. F. Pregenzer, J. Retief, B. B. Spear and J. F. Waring, Microarray analysis in human hepatocytes suggests a mechanism for hepatotoxicity induced by trovafloxacin, Hepatology 41 (2005) 177-186; DOI: 10.1124/jpet.105.096347.10.1124/jpet.105.09634716299187Search in Google Scholar

Q. Sun, R. Zhu, F. W. Foss, Jr. and T. L. Macdonald, Mechanisms of trovafloxacin hepatotoxicity: studies of a model cyclopropylamine-containing system, Bioorg. Med. Chem. Lett. 17 (2007) 6682-6686; DOI: 10.1016/j.bmd.2007.10.070.Search in Google Scholar

Q. Sun, R. Zhu, F. W. Foss, Jr. and T. L. Macdonald, In vitro metabolism of a model cyclopropylamine to reactive intermediate: Insights into trovafloxacin-induced hepatotoxicity, Chem. Res. Toxicol. 21 (2008) 711-719; DOI: 10.1021/tx7003085.10.1021/tx700308518298092Search in Google Scholar

J. M. Domagala, Structure-activity and structure-side-effect relationships for the quinolone antibacterials, J. Antimicrob. Chemother. 33 (1994) 685-706; DOI: 10.1093/jac/33.4.685.10.1093/jac/33.4.6858056688Search in Google Scholar

G. S. Tillotson, Quinolones: structure-activity relationships and future predictions, J. Med. Microb. 44 (1996) 320-324; DOI: 10.1099/00222615-44-5-320.10.1099/00222615-44-5-320Search in Google Scholar

L. Mandell and G. Tillotson, Fluoroquinolone safety: An overview evaluating safety and antimicrobial activity profiles based on molecular structure categorized adverse effects, Can. J. Infec. Dis. 13 (2002) 54-61.Search in Google Scholar

Y. Tsuzuki, K. Tomita, K. Shibamori, Y. Sato, S. Kashimoto and K. Chiba, Synthesis and structure-activity relationships of novel 7-substituted 1,4 dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids as anti-tumor agents, part-2, J. Med. Chem. 47 (2004) 2097-2109; DOI: 10.1021/jm0304966.10.1021/jm0304966Search in Google Scholar

M. Paul, A. Gafter-Gvili, A. Fraser and L. Leibovici, The anti-cancer effects of quinolone antibiotics?, Eur. J. Clin. Microbiol. Infect. Dis. 26 (2007) 825-831; DOI: 10.1007/s10096-007-0375-4.10.1007/s10096-007-0375-4Search in Google Scholar

T. Norris and G. Ferry, Process for Preparing Quinolone and Naphthyridine Carboxylic Acids, U.S. Pat. 6,114,531, 5 Sep. 2005.Search in Google Scholar

E. Rubinstein, History of quinolones and their side-effects, Chemotherapy 47 (2001) 3-8; 44-48; DOI: 10.1159/000057838.10.1159/000057838Search in Google Scholar

P. J. Shaw, A. M. Fullerton, M. A. Scott, P. E. Ganey and R. A. Roth, The role of the hemostatic system in murine liver injury induced by coexposure to lipopolysaccharide and trovafloxacin, a drug with idiosyncratic liability, Toxicol. Appl. Pharmacol. 236 (2009) 293-300; DOI: 10.1016/j.taap.2009.01.018.10.1016/j.taap.2009.01.018Search in Google Scholar

C. A. Lipinski, F. Lombardo, B. W. Dominy and P. J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev. 23 (1997) 4-25; DOI: 10.1016/S0169-409X(00)00129-0.10.1016/S0169-409X(00)00129-0Search in Google Scholar

D. F. Veber, S. R. Johnson, H. Y. Cheng, B. R. Smith, K. W. Ward and K. D. Kopple, Molecular properties that influence the oral bioavailability of drug candidates, J. Med. Chem. 45 (2002) 2615-2623; DOI: 10.1021/jm020017n.10.1021/jm020017nSearch in Google Scholar

P. Ertl, B. Rohde and P. Selzer, Fast calculation of molecular polar surface area as a sum of fragent-based contributions and its application to the prediction of drug transport properties, J. Med. Chem. 43 (2000) 3714-3717; DOI: 10.1021/jm000942e.10.1021/jm000942eSearch in Google Scholar

H. O. Kalinowski, S. Berger and S. Braun, ¹³C-NMR Spektroskopie, Georg Thieme Verlag, Stuttgart 1984.Search in Google Scholar

R. M. Silverstein, C. C. Bassler and T. C. Morrill, Spectroscopic Identification of Organic Compounds, 5th ed., Wiley, New York 1991.Search in Google Scholar

G. Fardella, P. Barbetti, I. Chiappini and G. Grandolini, Quantitative analysis of fluoroquinolones by ¹H and ¹⁹F-NMR spectroscopy, Int. J. Pharm. 121 (1995) 123-127; DOI: 10:1016/0378-5173(95)00038-K.10.1016/0378-5173(95)00038-KSearch in Google Scholar

A. Zieba, A. Mašlankiewicz and J. Sitkovski, ¹H, ¹³C and ¹⁵N NMR spectra of ciprofloxacin, Magn. Reson. Chem. 42 (2004) 903-904; DOI: 10.1002/mrc.1468.10.1002/mrc.146815366066Search in Google Scholar