Synthesis and antibacterial properties of new N₄-acetylated hexahydro-2,7-dioxopyrido[2,3-f]quinoxaline-8-carboxylic acids

References

• Wise R, Andrews JM, Edwards LJ. In vitro activity of Bay 09867, a new quinoline derivative, compared with those of other antimicrobial agents. Antimicrob Agents Chemother 1983, 23, 559–564.
   PubMed Web of Science ®Google Scholar
• Grohe K. The chemistry of the quinolones: methods of synthesizing the quinolone ring system. In: Handbook of Experimental Pharmacology. Springer-Verlag, Berlin, Heidelberg, 1998, pp. 13–62.
   Google Scholar
• Li Q, Mitscher LA, Shen LL. The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med Res Rev 2000, 20, 231–293.
   PubMed Web of Science ®Google Scholar
• Zhanel GG, Ennis K, Vercaigne L, Walkty A, Gin AS, Embil J, Smith H, Hoban DJ. The new fluoroquinolones: focus on respiratory infections. Drugs 2002, 62, 13–59.
   PubMedGoogle Scholar
• Da Silva AD, De Almeida MV, De Souza MV, Couri MR. Biological activity and synthetic methodologies for the preparation of fluoroquinolones, a class of potent antibacterial agents. Curr Med Chem 2003, 10, 21–39.
   PubMed Web of Science ®Google Scholar
• Hagihara M, Kashiwase H, Katsube T, Kimura T, Komai T, Momota K, Ohmine T, Nishigaki T, Kimura S, Shimada K. Synthesis and anti-HIV activity of arylpiperazinyl fluoroquinolones: a new class of anti-HIV agents. Bioorg Med Chem Lett 1999, 9, 3063–3068.
   PubMed Web of Science ®Google Scholar
• Kimura F, Katsube T, Nishigaki T, Preparation of trifluoromethyl (piperazinyl)-quinolinecarboxylic acids as anti-HIV agents. Jpn Kokai Tokkyo Koho 1997; JP 09249568. Chem Abstr 1997, 127, 262703.
   Google Scholar
• Ohmine T, Katsube T, Tsuzaki Y, Kazui M, Kobayashi N, Komai T, Hagihara M, Nishigaki T, Iwamoto A, Kimura T, Kashiwase H, Yamashita M. Anti-HIV-1 activities and pharmacokinetics of new arylpiperazinyl fluoroquinolones. Bioorg Med Chem Lett 2002, 12, 739–742.
   PubMed Web of Science ®Google Scholar
• Filipponi E, Cruciani G, Tabarrini O, Cecchetti V, Fravolini A. QSAR study and VolSurf characterization of anti-HIV quinolone library. J Comput Aided Mol Des 2001, 15, 203–217.
   PubMedGoogle Scholar
• Mikiciuk-Olasik E, Trzebinski P, Nowak R, Kotelko B. Synthesis of new derivatives of 4-acylquinoxalin-2-ones with potential pharmacological activity. Acta Pol Pharm 1994, 51, 231–233.
   PubMedGoogle Scholar
• Roesner M, Billhardt-Troughton UM, Kirsch R, Kleim JP, Meichsner C, Riess G, Winkler I. Preparation of quinoxalinones as antiviral agents. Eur Pat Appl 1996; EP 708093: A1-19960424, 30 p.
   Google Scholar
• Meichsner C, Riess G, Kleim JP, Roesner M, Paessens A, Blunck M, Combination of quinoxalines and nucleosides for treating viral infection and preparation of the quinoxalines. Eur Pat Appl 1995; EP 657166. Chem Abstr 1995, 123, 228218.
   Google Scholar
• Billhardt UM, RoesnerM, Riess G, Winkler I, Bender R. 3,4-Dihydro-2-quinoxalinones, 3,4-dihydro-2-quinoxalinethiones and analogs, methods for their preparation and their use as virucides. Eur Pat Appl 1992; EP 509398. Chem Abstr 1993, 118, 234088.
   Google Scholar
• Kleim JP, Bender R, Kirsch R, Meichsner C, Paessens A, Rösner M, Rübsamen-Waigmann H, Kaiser R, Wichers M, Schneweis KE. Preclinical evaluation of HBY 097, a new nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 replication. Antimicrob Agents Chemother 1995, 39, 2253–2257.
   PubMedGoogle Scholar
• Rübsamen-Waigmann H, Huguenel E, Paessens A, Kleim JP, Wainberg MA, Shah A. Second-generation non-nucleosidic reverse transcriptase inhibitor HBY097 and HIV-1 viral load. Lancet 1997, 349, 1517.
   PubMedGoogle Scholar
• Kleim JP, Winkler I, Rösner M, Kirsch R, Rübsamen-Waigmann H, Paessens A, Riess G. In vitro selection for different mutational patterns in the HIV-1 reverse transcriptase using high and low selective pressure of the nonnucleoside reverse transcriptase inhibitor HBY 097. Virology 1997, 231, 112–118.
   PubMedGoogle Scholar
• Hayashi S, Jayesekera D, Jayewardene A, Shah A, Thevanayagam L, Aweeka F. Altered pharmacokinetics of indinavir by a novel nonnucleoside reverse transcriptase inhibitor (HBY-097): a pharmacokinetic evaluation in HIV-positive patients. J Clin Pharmacol 1999, 39, 1085–1093.
   PubMedGoogle Scholar
• Rübsamen-Waigmann H, Huguenel E, Shah A, Paessens A, Ruoff HJ, von Briesen H, Immelmann A, Dietrich U, Wainberg MA. Resistance mutations selected in vivo under therapy with anti-HIV drug HBY 097 differ from resistance pattern selected in vitro. Antiviral Res 1999, 42, 15–24.
   PubMedGoogle Scholar
• Rizzo RC, Udier-Blagovic M, Wang DP, Watkins EK, Kroeger Smith MB, Smith RH Jr, Tirado-Rives J, Jorgensen WL. Prediction of activity for nonnucleoside inhibitors with HIV-1 reverse transcriptase based on Monte Carlo simulations. J Med Chem 2002, 45, 2970–2987.
   PubMed Web of Science ®Google Scholar
• Balzarini J, Karlsson A, Meichsner C, Paessens A, Riess G, De Clercq E, Kleim JP. Resistance pattern of human immunodeficiency virus type 1 reverse transcriptase to quinoxaline S-2720. J Virol 1994, 68, 7986–7992.
   PubMed Web of Science ®Google Scholar
• Kleim JP, Bender R, Billhardt UM, Meichsner C, Riess G, Rösner M, Winkler I, Paessens A. Activity of a novel quinoxaline derivative against human immunodeficiency virus type 1 reverse transcriptase and viral replication. Antimicrob Agents Chemother 1993, 37, 1659–1664.
   PubMed Web of Science ®Google Scholar
• Arasteh K, Wood R, Müller M, Prince W, Cass L, Moore KH, Dallow N, Jones A, Klein A, Burt V, Kleim JP. GW420867X administered to HIV-1-infected patients alone and in combination with lamivudine and zidovudine. HIV Clin Trials 2001, 2, 307–316.
   PubMedGoogle Scholar
• Mutch PJ, Dear GJ, Ismail IM. Formation of a defluorinated metabolite of a quinoxaline antiviral drug catalysed by human cytochrome P450 1A2. J Pharm Pharmacol 2001, 53, 403–408.
   PubMed Web of Science ®Google Scholar
• Moore KH, Cass LM, Dallow N, Hardman TC, Jones A, Boyce M, Prince WT. Pharmacokinetics and safety of escalating single and repeat oral doses of GW420867X, a novel non-nucleoside reverse transcriptase inhibitor. Eur J Clin Pharmacol 2001, 56, 805–811.
   PubMedGoogle Scholar
• Thomas S, Cass L, Prince W, Segal M. Brain and CSF entry of the novel non-nucleoside reverse transcriptase inhibitor, GW420867X. Neuroreport 2000, 11, 3811–3815.
   PubMedGoogle Scholar
• Balzarini J, De Clercq E, Carbonez A, Burt V, Kleim JP. Long-term exposure of HIV type 1-infected cell cultures to combinations of the novel quinoxaline GW420867X with lamivudine, abacavir, and a variety of nonnucleoside reverse transcriptase inhibitors. AIDS Res Hum Retroviruses 2000, 16, 517–528.
   PubMed Web of Science ®Google Scholar
• GraulA, Rabasseda X, Castañer J. GW-420867X. Anti-HIV, Reverse transcriptase inhibitor. Drugs Fut 2000, 25, 24–28.
   Google Scholar
• Al-Hiari YM, Qaisi AM, AbuShuheil MY, El-Abadelah MM, Voelter W. Synthesis and antibacterial potency of 4-methyl-2,7-dioxo-1,2,3,4,7,10-hexahydropyrido[2,3-f]-quinoxaline-8-carboxylic acid, selected [a]-fused heterocycles and acyclic precursors. Zeitschrift fuer Naturforschung B: Chem Sci 2007, 62B, 1453–1458.
   Google Scholar
• Chicharro R, De Castro S, Reino RL, Aran JV. Synthesis of tri- and tetracyclic condensed quinoxalin-2-ones fused across the C-3–N-4 bond. Eur J Org Chem 2003, 12, 2314–2326.
   Google Scholar
• Abu Shuheil MY, Hassuneh MR, Al-Hiari YM, Qaisi AM, El-Abadelah MM, Heterocyclyes [h]-fused onto 4-oxoquinoline-3-carboxylic acid III—facile synthesis and antitumor activity of model heterocycles [a] fused onto pyrido[2,3-f]-quinoloxaline-3-carboxylic acids. Heterocycles 2007, 71, 2155–2172.
   Google Scholar
• Al-Hiari YM, Al-Mazari IS, Shakya AK, Darwish RM, Abu-Dahab R. Synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives. Molecules 2007, 12, 1240–1258.
   PubMedGoogle Scholar
• Sakae N, Yazaki A, Kuramoto Y, Yoshida J, Niino Y, Oshita Y, Hirao Y, Hayashi N, Amano H. Preparation of quinolinecarboxylic acid derivatives as bactericides. PCT Int. Appl. 1998; WO 98 23, 592. Chem Abstr 1998, 129, 41087j.
   Google Scholar
• Morita S, Otsubo K, Matsubara J, Ohtani T, Kawano Y, Ohmori K, Ohguro K, Uchida M. Synthesis of possible metabolites of 1-cyclopropyl-1,4-dihydro-6-fluoro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (Grepafloxacin, OPC-17116). Chem Pharm Bull 1995, 43, 2246–2252.
   PubMedGoogle Scholar
• Sarma MR, Kumar NV, Prasad ASR, Eswaraiah S, Prabhakar C, Reddy GO, Kumar MS, Sadhukhan AK, Venkateswarlu A, Reddy KA. Synthesis and biological activity of novel antibacterial quinolones. Indian J Chem 2001, 40B, 331–335.
   Google Scholar