Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2014 (2014), Article ID 563406, 21 pages
http://dx.doi.org/10.1155/2014/563406
Review Article

Pharmacological Profile of Quinoxalinone

1Laboratoire National de Contrôle des Médicaments, D M P, Ministère de la Santé, Madinat Al Irnane, BP 6206, Rabat, Morocco
2Unité de la Radioimmunoanalyse, Centre National d’Etudes Scientifiques et Techniques d’Energie Nucléaire, BP 1382, Rabat, Morocco
3Laboratoire de Chimie Thérapeutique, Faculté de Médecine et de Pharmacie de Rabat-Souissi, Université Mohamed V, BP 6203, Rabat, Morocco
4Laboratoire de Chimie Organique Hétérocyclique, RAC 21, Université Mohammed V-Agdal, Rabat, Morocco

Received 19 May 2013; Accepted 22 October 2013; Published 9 February 2014

Academic Editor: Marc Visseaux

Copyright © 2014 Youssef Ramli et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. K. Fridkin, J. C. Hageman, M. Morrison et al., “Methicillin-resistant Staphylococcus aureus disease in three communities,” The New England Journal of Medicine, vol. 352, no. 14, pp. 1436–1505, 2005. View at Publisher · View at Google Scholar · View at Scopus
  2. W. T. Siebert, N. Moreland, and T. W. Williams Jr., “Methicillin-resistant Staphylococcus epidermidis,” Southern Medical Journal, vol. 71, no. 11, pp. 1353–1355, 1978. View at Google Scholar · View at Scopus
  3. A. H. C. Uttley, N. Woodford, A. P. Johnson et al., “Vancomycin-resistant enterococci,” The Lancet, vol. 342, no. 8871, pp. 615–617, 1993. View at Google Scholar · View at Scopus
  4. J. Ohkanda and A. Katoh, “N-hydroxyamide-containing heterocycles: synthesis, reactivities, and iron(III)-chelating properties,” Reviews on Heteroatom Chemistry, vol. 18, pp. 87–118, 1998. View at Google Scholar · View at Scopus
  5. A. Dell, D. H. Williams, and H. R. Morris, “Structure revision of the antibiotic echinomycin,” Journal of the American Chemical Society, vol. 97, no. 9, pp. 2497–2502, 1975. View at Google Scholar · View at Scopus
  6. C. Bailly, S. Echepare, F. Gago, and M. J. Waring, “Recognition elements that determine affinity and sequence-specific binding to DNA of 2QN, a biosynthetic bis-quinoline analogue of echinomycin,” Anti-Cancer Drug Design, vol. 14, no. 3, pp. 291–303, 1999. View at Google Scholar · View at Scopus
  7. K. Sato, O. Shiratori, and K. Katagiri, “The mode of action of quinoxaline antibiotics. Interaction of quinomycin A with deoxyribonucleic acid,” Journal of Antibiotics, vol. 20, no. 5, pp. 270–276, 1967. View at Google Scholar · View at Scopus
  8. S. A. Kotharkar and D. B. Shinde, “Synthesis of antimicrobial 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 24, pp. 6181–6184, 2006. View at Google Scholar
  9. A. Carta, M. Loriga, S. Zanetti, and L. A. Sechi, “Quinoxalin-2-ones. Part 5: synthesis and antimicrobial evaluation of 3-alkyl-, 3-halomethyl- and 3-carboxyethylquinoxaline-2-ones variously substituted on the benzo-moiety,” Farmaco, vol. 58, no. 12, pp. 1251–1255, 2003. View at Publisher · View at Google Scholar · View at Scopus
  10. O. I. El-Sabbagh, M. E. El-Sadek, S. M. Lashine, S. H. Yassin, and S. M. El-Nabtity, “Synthesis of new 2(1H)-quinoxalinone derivatives for antimicrobial and antiinflammatory evaluation,” Medicinal Chemistry Research, vol. 18, no. 9, pp. 782–797, 2009. View at Publisher · View at Google Scholar · View at Scopus
  11. S. A. Khan, P. Mullick, S. Pandit, and D. Kaushik, “Synthesis of hydrazones derivatives of quinoxalinone- prospective antimicrobial and antiinflammatory agents,” Acta Poloniae Pharmaceutica, vol. 66, no. 2, pp. 169–172, 2009. View at Google Scholar · View at Scopus
  12. H. Ishikawa, T. Sugiyama, K. Kurita, and A. Yokoyama, “Synthesis and antimicrobial activity of 2,3-bis(bromomethyl)quinoxaline derivatives,” Bioorganic Chemistry, vol. 41-42, pp. 1–5, 2012. View at Publisher · View at Google Scholar · View at Scopus
  13. Y. Estevez, M. Quiliano, A. Burguete et al., “Trypanocidal properties, structure-activity relationship and computational studies of quinoxaline 1,4-di-N-oxide derivatives,” Experimental Parasitology, vol. 127, pp. 745–751, 2011. View at Google Scholar
  14. O. M. Ghoneim, D. A. Ibrahim, I. M. El-Deeb, S. H. Lee, and R. G. Booth, “A novel potential therapeutic avenue for autism: design, synthesis and pharmacophore generation of SSRIs with dual action,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 22, pp. 6714–6723, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. M. Suresh, P. Lavanya, D. Sudhakar, K. Vasu, and C. Venkata Rao, “Synthesis and biological activity of 8-chloro-[1, 2, 4]triazolo[4, 3-a]quinoxalines,” Journal of Chemical and Pharmaceutical Research, vol. 2, no. 1, pp. 497–504, 2010. View at Google Scholar
  16. R. V. Ghadage and P. J. Shirote, “Antimicrobial activities of some substituted quinoxalin-2(1H)-one derivatives,” Journal of Chemical and Pharmaceutical Research, vol. 3, no. 5, pp. 260–266, 2011. View at Google Scholar · View at Scopus
  17. K. Aravind, A. Ganesh, and D. Ashok, “Microwave assisted synthesis, characterization and antibacterial activity of quinoxaline derivatives,” Journal of Chemical and Pharmaceutical Research, vol. 5, no. 2, pp. 48–52, 2013. View at Google Scholar
  18. G. K. Raoa, R. B. Kotnal, and P. N. Sanjay Paib, “In vitro screening of quinoxaline-2-one derivatives for antitubercular activity,” Journal of Chemical and Pharmaceutical Research, vol. 2, no. 3, pp. 368–373, 2010. View at Google Scholar
  19. O. O. Ajani, C. A. Obafemi, O. C. Nwinyi, and D. A. Akinpelu, “Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives,” Bioorganic and Medicinal Chemistry, vol. 18, no. 1, pp. 214–221, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. N. Rivera, Y. M. Ponce, V. J. Arán, C. Martínez, and F. Malagón, “Biological assay of a novel quinoxalinone with antimalarial efficacy on Plasmodium yoelii yoelii,” Parasitology Research, vol. 112, no. 4, pp. 1523–1527, 2013. View at Google Scholar
  21. A. Carta, P. Sanna, L. Gherardini, D. Usai, and S. Zanetti, “Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial, antifungal and anticancer agents,” Farmaco, vol. 56, no. 12, pp. 933–938, 2001. View at Publisher · View at Google Scholar · View at Scopus
  22. A. Burguete, E. Pontiki, D. Hadjipavlou-Litina et al., “Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 23, pp. 6439–6443, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. J. J. Li, K. G. Carson, B. K. Trivedi et al., “Synthesis and structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-molecule antagonists for interleukin-8 receptor,” Bioorganic and Medicinal Chemistry, vol. 11, no. 17, pp. 3777–3790, 2003. View at Publisher · View at Google Scholar · View at Scopus
  24. J.-P. Kleim, R. Bender, R. Kirsch et al., “Preclinical evaluation of HBY 097, a new nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 replication,” Antimicrobial Agents and Chemotherapy, vol. 39, no. 10, pp. 2253–2257, 1995. View at Google Scholar · View at Scopus
  25. J. Balzarini, A. Karlsson, C. Meichsner et al., “Resistance pattern of human immunodeficiency virus type 1 reverse transcriptase to quinoxaline S-2720,” Virology, vol. 68, p. 1986, 1994. View at Google Scholar
  26. J. Gris, R. Glisoni, L. Fabian, B. Fernández, and A. G. Moglioni, “Synthesis of potential chemotherapic quinoxalinone derivatives by biocatalysis or microwave-assisted Hinsberg reaction,” Tetrahedron Letters, vol. 49, no. 6, pp. 1053–1056, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. B. Xu, Y. Sun, Y. Guo, Y. Cao, and T. Yu, “Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors,” Bioorganic and Medicinal Chemistry, vol. 17, no. 7, pp. 2767–2774, 2009. View at Publisher · View at Google Scholar · View at Scopus
  28. H. Rübsamen-Waigmann, E. Huguenel, A. Shah et al., “Resistance mutations selected in vivo under therapy with anti-HIV drug HBY 097 differ from resistance pattern selected in vitro,” Antiviral Research, vol. 42, no. 1, pp. 15–24, 1999. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Patel, R. J. McHugh Jr., B. C. Cordova et al., “Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 10, no. 15, pp. 1729–1731, 2000. View at Publisher · View at Google Scholar · View at Scopus
  30. I. A. I. Ali, I. A. Al-Masoudi, H. G. Hassan, and N. A. Al-Masoudi, “Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl)quinoxalin-2-ones and 2-(pent-4-enyloxy)quinoxalines,” Chemistry of Heterocyclic Compounds, vol. 43, no. 8, pp. 1052–1059, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. J.-P. Kleim, R. Bender, U.-M. Billhardt et al., “Activity of a novel quinoxaline derivative against human immunodeficiency virus type 1 reverse transcriptase and viral replication,” Antimicrobial Agents and Chemotherapy, vol. 37, no. 8, pp. 1659–1664, 1993. View at Google Scholar · View at Scopus
  32. G. W. Bemis and J. P. Duffy, “Quinoxalines useful as inhibitors of protein kinases,” WO 2005/056547 A2, 2005. View at Google Scholar
  33. C. Kalinski, M. Umkehrer, G. Ross, J. Kolb, C. Burdack, and W. Hiller, “Highly substituted indol-2-ones, quinoxalin-2-ones and benzodiazepin-2,5-diones via a new Ugi(4CR)-Pd assisted N-aryl amidation strategy,” Tetrahedron Letters, vol. 47, no. 20, pp. 3423–3426, 2006. View at Publisher · View at Google Scholar · View at Scopus
  34. J. Dudash Jr., Y. Zhang, J. B. Moore et al., “Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 21, pp. 4790–4793, 2005. View at Publisher · View at Google Scholar · View at Scopus
  35. S. A. Galal, A. S. Abdelsamie, H. Tokuda et al., “Part I: synthesis, cancer chemopreventive activity and molecular docking study of novel quinoxaline derivatives,” European Journal of Medicinal Chemistry, vol. 46, no. 1, pp. 327–340, 2011. View at Publisher · View at Google Scholar · View at Scopus
  36. C. Avendano and J. C. Menendez, “Inhibitors of Multidrug Resistance to Antitumor Agents (MDR),” Current Medicinal Chemistry, vol. 9, pp. 159–193, 2002. View at Google Scholar
  37. J. Robert, “Approaches to multidrug resistance reversal,” Expert Opinion on Investigational Drugs, vol. 7, no. 6, pp. 929–939, 1998. View at Publisher · View at Google Scholar · View at Scopus
  38. A. Aszalos, A. Ladányi, J. Bocsi, and B. Szende, “Induction of apoptosis in MDR1 expressing cells by daunorubicin with combinations of suboptimal concentrations of P-glycoprotein modulators,” Cancer Letters, vol. 167, no. 2, pp. 157–162, 2001. View at Publisher · View at Google Scholar · View at Scopus
  39. E. C. Lopes, M. Garcia, F. Benavides, J. Shen, C. J. Conti, E. Alvarez et al., “Multidrug resistance modulators PSC 833 and CsA show differential capacity to induce apoptosis in lymphoid leukemia cell lines independently of their MDR phenotype,” Leukemia Research, vol. 27, pp. 413–423, 2003. View at Google Scholar
  40. F. Shen, S. Chu, A. K. Bence, B. Bailey, X. Xue, and P. A. Erickson, “Quantitation of doxorubicin uptake, efflux, and modulation of multidrug resistance (MDR) in MDR human cancer cells,” Journal of Pharmacology and Experimental Therapeutics, vol. 324, pp. 95–102, 2008. View at Google Scholar
  41. P. Mistry, A. J. Stewart, W. Dangerfield et al., “In vitro and in vivo reversal of P-glycoprotein-mediated multidrug resistance by a novel potent modulator, XR9576,” Cancer Research, vol. 61, no. 2, pp. 749–758, 2001. View at Google Scholar · View at Scopus
  42. D. S. Lawrence, J. E. Copper, and C. D. Smith, “Structure: activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists,” Journal of Medicinal Chemistry, vol. 44, pp. 594–601, 2001. View at Google Scholar
  43. L.-R. Sun, X. Li, Y.-N. Cheng et al., “Reversal effect of substituted 1,3-dimethyl-1H-quinoxalin-2-ones on multidrug resistance in adriamycin-resistant K562/A02 cells,” Biomedicine and Pharmacotherapy, vol. 63, no. 3, pp. 202–208, 2009. View at Publisher · View at Google Scholar · View at Scopus
  44. M. Loriga, M. Fiore, P. Sanna, and G. Paglietti, “Quinoxaline chemistry. Part 4. 2-(R)-anilinoquinoxalines as nonclassical antifolate agents: synthesis, structure elucidation and evaluation of in vitro anticancer activity,” Farmaco, vol. 50, no. 5, pp. 289–301, 1995. View at Google Scholar · View at Scopus
  45. M. Loriga, M. Fiore, P. Sanna, and G. Paglietti, “Quinoxaline chemistry. Part 5. 2-(R)-benzylaminoquinoxalines as nonclassical antifolate agents: synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 51, no. 8-9, pp. 559–568, 1996. View at Google Scholar · View at Scopus
  46. M. Loriga, S. Piras, P. Sanna, and G. Paglietti, “Quinoxaline chemistry. Part 7. 2-[aminobenzoates]- and 2-[aminobenzoylglutamate]-quinoxalines as classical antifolate agents. Synthesis and evaluation of in vitro anticancer, anti-HIV and antifungal activity,” Farmaco, vol. 52, no. 3, pp. 157–166, 1997. View at Google Scholar · View at Scopus
  47. M. Loriga, P. Moro, P. Sanna, G. Paglietti, and S. Zanetti, “Quinoxaline chemistry. Part 8. 2-[anilino]-3- [carboxy]-6(7)-substituted quinoxalines as non classical antifolate agents. Synthesis and evaluation of in vitro anticancer, anti-HIV and antifungal activity,” Farmaco, vol. 52, no. 8-9, pp. 531–537, 1997. View at Google Scholar · View at Scopus
  48. M. Loriga, G. Vitale, and G. Paglietti, “Quinoxaline chemistry. Part 9. Quinoxaline analogues of trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) and its precursors. Synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 53, no. 2, pp. 139–149, 1998. View at Google Scholar · View at Scopus
  49. G. Vitale, P. Corona, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. part 10. Quinoxaline 10-oxa-analogues of trimetrexate (TMQ) and of 5,8-dideazafolic acid. Synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 53, no. 2, pp. 150–159, 1998. View at Google Scholar · View at Scopus
  50. P. Corona, G. Vitale, M. Loriga, G. Paglietti, and M. P. Costi, “Quinoxaline chemistry. Part 11.3-Phenyl-2[phenoxy- and phenoxymethyl]- 6(7) or 6,8-substituted quinoxalines and n-[4-(6(7)-substituted or 6,8- disubstituted-3-phenylquinoxalin-2,yl) hydroxy or hydroxymethyl] benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity and enzymatic inhibitory activity against dihydrofolate reductase and thymidylate synthase,” Farmaco, vol. 53, no. 7, pp. 480–493, 1998. View at Publisher · View at Google Scholar · View at Scopus
  51. G. Vitale, P. Corona, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. Part 12. 3-Carboxy-2[phenoxyl-6(7)substituted quinoxalines and N-[4-(6(7) substituted-3-carboxyquinoxalin- 2-yl)hydroxy]-benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 53, no. 8-9, pp. 594–601, 1998. View at Publisher · View at Google Scholar · View at Scopus
  52. P. Corona, G. Vitale, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. Part 13: 3-carboxy-2-benzylamino-substituted quinoxalines and N-[4-[(3-carboxyquinoxalin-2-yl) aminomethyl]benzoyl]-L-glutamates: synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 55, no. 2, pp. 77–86, 2000. View at Publisher · View at Google Scholar · View at Scopus
  53. P. Corona, G. Vitale, M. Loriga, S. Alleca, and G. Paglietti, “Pirrolo[1, 2-, a]quinoxalines analogues of antifolic trimetrexate and methotrexate,” in Proceedings of the 16th International Symposium on Medicinal Chemistry, p. 526, Bologna, Italy, September 2000.
  54. S. Piras, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. Part 14. 4-(2-Quinoxalylamino)-phenylacetates and 4-(2-quinoxalylamino)-phenylacetyl-l-glutamates as analogues-homologues of classical antifolate agents: synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 57, no. 1, pp. 1–8, 2002. View at Google Scholar
  55. S. Piras, M. Loriga, and G. Paglietti, “Quinoxalines analogues-homologues of methotrexate,” in Proceedings of the Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry (HGIP JMMC), p. 141, Budapest, Hungary, September2001.
  56. P. Corona, M. Loriga, G. Paglietti, P. la Colla, M. G. Setzu, and R. Loddo, “Imidazo[1, 2-, a]- and 1, 2, 4-triazolo[4, 3-, a]quinoxalines analogues of antifolic trimetrexate and methotrexate,” in Proceedings of the Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry (HGIPJMMC), p. 64, Budapest, Hungary, September2001.
  57. G. Vitale, M. Loriga, G. Paglietti et al., “Quinoxalines analogues of thymitaq and 2-(arylthio)quinoxalines analogues of trimetrexate and methotrexate,” in Proceedings of the of Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry (HGIP JMMC), p. 184, Budapest, Hungary, September2001.
  58. S. Piras, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. Part XVII. Methyl [4-(substituted 2-quinoxalinyloxy) phenyl] acetates and ethyl N-{[4-(substituted 2-quinoxalinyloxy) phenyl] acetyl} glutamates analogs of methotrexate: synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 59, no. 3, pp. 185–194, 2004. View at Publisher · View at Google Scholar · View at Scopus
  59. S. T. Hazeldine, L. Polin, J. Kushner et al., “II. Synthesis and biological evaluation of some bioisosteres and congeners of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxylphenoxy}propionic acid (XK469),” Journal of Medicinal Chemistry, vol. 45, no. 14, pp. 3130–3137, 2002. View at Publisher · View at Google Scholar · View at Scopus
  60. P. Corona, A. Carta, M. Loriga, G. Vitale, and G. Paglietti, “Synthesis and in vitro antitumor activity of new quinoxaline derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1579–1591, 2009. View at Publisher · View at Google Scholar · View at Scopus
  61. Q. Weng, D. Wang, P. Guo et al., “Q39, a novel synthetic Quinoxaline 1,4-Di-N-oxide compound with anti-cancer activity in hypoxia,” European Journal of Pharmacology, vol. 581, no. 3, pp. 262–269, 2008. View at Google Scholar
  62. S. Piras, M. Loriga, and G. Paglietti, “Quinoxaline chemistry. Part XVII. Methyl [4-(substituted 2-quinoxalinyloxy) phenyl] acetates and ethyl N-{[4-(substituted 2-quinoxalinyloxy) phenyl] acetyl} glutamates analogs of methotrexate: synthesis and evaluation of in vitro anticancer activity,” Farmaco, vol. 59, no. 3, pp. 185–194, 2004. View at Publisher · View at Google Scholar · View at Scopus
  63. J. Miyashiro, K. W. Woods, C. H. Park et al., “Synthesis and SAR of novel tricyclic quinoxalinone inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1),” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 15, pp. 4050–4054, 2009. View at Publisher · View at Google Scholar · View at Scopus
  64. R. Teja, S. Kapu, S. Kadiyala, V. Dhanapal, and A. N. Raman, Journal of Saudi Chemical Society. In press.
  65. W. Ginzinger, G. Mühlgassner, V. B. Arion et al., “A SAR study of novel antiproliferative ruthenium and osmium complexes with quinoxalinone ligands in human cancer cell lines,” Journal of Medicinal Chemistry, vol. 55, no. 7, pp. 3398–3413, 2012. View at Publisher · View at Google Scholar · View at Scopus
  66. H. Hirai, I. Takahashi-Suziki, T. Shimomura et al., “Potent anti-tumor activity of a macrocycle-quinoxalinone class pan-Cdk inhibitor in vitro and in vivo,” Investigational New Drugs, vol. 29, no. 4, pp. 534–543, 2011. View at Publisher · View at Google Scholar · View at Scopus
  67. M. Weïwer, J. Spoonamore, J. Wei et al., “A potent and selective quinoxalinone-based STK33 inhibitor does not Show Synthetic Lethality in KRAS-Dependent Cells,” ACS Medicinal Chemistry Letters, vol. 3, no. 12, pp. 1034–1038, 2012. View at Google Scholar
  68. H. Yuan, X. Li, X. Qu, L. Sun, W. Xu, and W. Tang, “Synthesis and primary evaluation of quinoxalinone derivatives as potent modulators of multidrug resistance,” Medicinal Chemistry Research, vol. 18, no. 8, pp. 671–682, 2009. View at Publisher · View at Google Scholar · View at Scopus
  69. F. Grant, S. Bartulis, L. Brogley et al., “Alpha-amino acid derivatives and use thereof as medicines,” ,WO 03/093245 A1, 2003. View at Google Scholar
  70. A. Bayoumi, A. Ghiaty, A. El-Morsy, H. Abul-Khair, M. H. Hassan, and S. Elmeligie, “Synthesis and evaluation of some new 1, 2, 4-triazolo(4, 3-a)quinoxalin-4-5H-one derivatives as AMPA receptor antagonists,” Bulletin of Faculty of Pharmacy, Cairo University, vol. 50, pp. 141–146, 2012. View at Google Scholar
  71. J. Hauptmann and J. Stürzebecher, “Synthetic inhibitors of thrombin and factor Xa: from Bench to bedside,” Thrombosis Research, vol. 93, no. 5, pp. 203–241, 1999. View at Google Scholar
  72. A. E. P. Adang and J. B. M. Rewinkel, “A new generation of orally active antithrombotics: comparing strategies in the GPllb/Illa, thrombin and factor XA areas,” Drugs of the Future, vol. 25, no. 4, pp. 369–383, 2000. View at Google Scholar · View at Scopus
  73. J. M. Fevig and R. R. Wexler, in Annual Reports in Medicinal Chemistry, W. Greenlee, Ed., vol. 34, p. 81, Academic Press, New York, NY, USA, 1999.
  74. U. J. Ries, H. W. M. Priepke, N. H. Hauel et al., “Heterocyclicthrombin inhibitors. Part 2: quinoxalinone derivatives as novel,potent antithrombotic agents,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 14, pp. 2297–2302, 2003. View at Publisher · View at Google Scholar · View at Scopus
  75. WHO, “Definition, diagnosis and classification of diabetes mellitus and its complications, 1999,” Report of a WHO Consultation, WHO, Geneva, Switzerland, 2003. View at Google Scholar
  76. S. Wild, G. Roglic, R. Sicree, A. Green, and H. King, “Global burden of diabetes mellitus in the year 2000,” in Global Burden of Disease, 2000. View at Google Scholar
  77. R. J. Marles and N. R. Farnsworth, “Antidiabetic plants and their active constituents,” Phytomedicine, vol. 2, no. 2, pp. 137–189, 1995. View at Google Scholar · View at Scopus
  78. Y. Yang, S. Zhang, B. Wu et al., “An efficient synthesis of quinoxalinone derivatives as potent inhibitors of aldose reductase,” ChemMedChem, vol. 7, no. 5, pp. 823–835, 2012. View at Publisher · View at Google Scholar · View at Scopus
  79. K.-H. Kim, A. Maderna, M. E. Schnute et al., “Imidazo[1,5-a]quinoxalines as irreversible BTK inhibitors for the treatment of rheumatoid arthritis,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 21, pp. 6258–6263, 2011. View at Publisher · View at Google Scholar · View at Scopus
  80. D. Peters, J. K. Christensen, K. Harpsoe, and T. Liljefors, “Novel quinoxaline derivatives and their medical use,” WO 2007/060144 A2, 2007. View at Google Scholar