Recent advances in the research of quinoxalinone derivatives

Drugs of the Future

Volumn 31, Issue 11, 2006, Pages 979-989

  Li, Xun ^a   Yang, Kang Hui ^a   Li, Wei Lu ^b   Xu, Wen Fang ^a  

^a SHANDONG UNIVERSITY   (China)

^b SHANDONG MEDICAL COLLEGE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 (1H INDOL 2 YLCARBONYL) 4 [3 (ISOPROPYLAMINO)PYRIDINYL]PIPERAZINE; 2 ETHYL 7 FLUORO 1,2,3,4 TETRAHYDRO 3 OXO 1 QUINOXALINECARBOXYLIC ACID ISOPROPYL ESTER; 2,3 QUINOXALINEDIONE DERIVATIVE; 3 [(4,7 DICHLORO 2 BENZOXAZOLYLMETHYL)AMINO] 5 ETHYL 6 METHYL 2(1H) PYRIDONE; 4 (2 CYCLOPROPYLVINYL) 5,6 DIFLUORO 3,4 DIHYDRO 4 TRIFLUOROMETHYL 2(1H) QUINAZOLINONE; 4 CYCLOPROPYLETHYNYL 5,6 DIFLUORO 3,4 DIHYDRO 4 TRIFLUOROMETHYL 2(1H) QUINAZOLINONE; 6 CHLORO 4 (2 CYCLOPROPYLVINYL) 3,4 DIHYDRO 4 TRIFLUOROMETHYL 2(1H) QUINAZOLINONE; 6 CHLORO 4 CYCLOPROPYLETHYNYL 3,4 DIHYDRO 4 TRIFLUOROMETHYL 2(1H) QUINAZOLINONE; ABACAVIR; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; EFAVIRENZ; GLYCOGEN PHOSPHORYLASE; GLYCOPROTEIN P INHIBITOR; IONOPHORE; LAMIVUDINE; N [4 CHLORO 3 (3 METHYL 2 BUTENYLOXY)PHENYL] 2 METHYL 3 FURANCARBOTHIOAMIDE; NEVIRAPINE; PANADIPLON; QUINOXALINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; S 2720; TALVIRALINE; UNCLASSIFIED DRUG;

ACETYLATION; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CLINICAL TRIAL; DRUG POTENCY; DRUG RESEARCH; DRUG SYNTHESIS; DRUG WITHDRAWAL; ENZYME INHIBITION; GENERALIZED ANXIETY DISORDER; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HYDROGENATION; LIVER TOXICITY; METHYLATION; MICROWAVE RADIATION; MULTIDRUG RESISTANCE; NONHUMAN; OXIDATION; PANIC; POLYMERIZATION; REVIEW; SOLID PHASE EXTRACTION; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION; THROMBOEMBOLISM;

EID: 33846557275     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2006.031.11.1037128     Document Type: Review

References (31)

1. Gao, X.M., Luo, W.P., Shen, X.F. et al. Synthesis of herbicide quizalofop-ethyl. Pesticides 1998, 37(7): 12-3.
2. Li, X., Hu, Q.P., Cui, X.G. et al. An improved synthesis of 6-chloro-1H-quinoxalin-2-one. Chin J Org Chem 2004, 24(7): 767-9.
3. Li, X., Hu, Q.P., Cui, X.G. et al. An efficient approach to 6,7-disubstituted-1H-quinoxalin-2-ones. Chin Chem Lett 2004, 15(12): 1400-2.
4. Li, X., Wang, D.H., Xu, W.F. et al. A novel regioselective synthesis of substituted 1,3-dimethyl-1H-quinoxalin-2-ones from aniline derivatives. Heterocycles 2005, 65(9): 2741-51.
5. Li, X., Wang, D.H., Xu, W.F. et al. A novel approach to 3-methyl-1H-quinoxalin-2-ones. Syn Comm 2005, 35: 2553-60.
6. Wu, X.H., Liu, G., Zhang, J. et al. Solution-phase reductive cyclization of 2-quinoxalinol analogs: Systematic study of parallel synthesis. Mol Divers 2004, 8(2): 165-74.
7. Acharya, A.N., Ostresh, Jm., Houghten, R.A. Solid-phase parallel synthesis of trisubstituted dihydroimidazolyl dihydroquinoxalin-2(1H)-ones. Tetrahedron 2002, 58(2): 221-5.
8. Krchòák, V., Szabo, L., Vágner, J. A solid phase traceless synthesis of quinoxalinones. Tetrahedron Lett 2000, 41(16): 2835-8.
9. Carta, A., Sanna, P., Gherardini, L. et al. Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial, antifungal and anticancer agents. Il Farmaco 2001, 56: 933-8.
10. Hashiba, I., Hatanaka, M. (Nissan Chemical Industries, Ltd.). Process for producing 6-substituted 2(1H)-quinoxalinone. WO 9522531.
11. Willardsen, J.A., Dudley, D.A., Cody, W.L. et al. Design, synthesis, and biological activity of potent and selective inhibitors of blood coagulation factor Xa. J Med Chem 2004, 47(16): 4089-99.
12. Nixey, T., Tempest, P., Hulme, C. Two-step solution-phase synthesis of novel quinoxalinones utilizing a UDC (Ugi/de-Boc/cyclize) strategy. Tetrahedron Lett 2002, 43(9): 1637-9.
13. Zhang, W., Tempest, P. Highly efficient microwave assisted fluorous Ugi and post condensation reactions for benzimidazoles and quinoxalinones. Tetrahedron Lett 2004, 45(36): 6757-60.
14. Tung, C.L., Sun, C.M. Liquid phase synthesis of chiral quinoxalinones by microwave irradiation. Tetrahedron Lett 2004, 45(6): 1159-62.
15. Dudash, J., Zhang, Y., Moore, J.B. et al. Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors. Bioorg Med Chem Lett 2005, 15(21): 4790-3.
16. Patel, M., McHugh, R.J., Cordova, B.C. et al. Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem Lett 2000, 10(15): 1729-31.
17. Sanna, P., Carta, A., Loriga, M. et al. Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2. Il Farmaco 1999, 54(3): 161-8.
18. Sanna, P., Carta, A., Loriga, M. et al. Preparation and biological evaluation of 6/7-trifluoro methyl(nitro)-, 6,7-difluoro-3-alkyl(aryl)- substituted-quinoxalin-2-ones. Part 3. Il Farmaco 1999, 54(3): 169-77.
19. Schwarzenbach, H. Expression of MDR1/P-glycoprotein, the multidrug resistance protein MRP, and the lung-resistance protein LRP in multiple myeloma. Med Oncol 2002, 19(2): 87-104.
20. Cole, S.P., Bhardwaj, G., Gerlach, J.H. et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 1992, 258: 1650-4.
21. Lawrence, D.S., Copper, J.E., Smith, C.D. Structure-activity studies of substituted quinoxalinones as multiple-drug-resistance antagonists. J Med Chem 2001, 44(4): 594-601.
22. Klopman, G., Shi, L.M., Ramu, A. Quantitative structure-activity relationship of multidrug resistance reversal agents. Mol Pharmacol 1997, 52(2): 323-34.
23. Garrigues, A., Loiseau, N., Delaforge, M. et al. Characterization of two pharmacophores on the multidrug transporter P-glycoprotein. Mol Pharmacol 2002, 62(6): 1288-98.
24. De Clercq, E. Non-nucleoside reverse transcriptase inhibitors (NNRTIs): Past, present, and future. Chem Biodivers 2004, 1: 44-64.
25. Balzarini, J., Karlsson, A., Meichsner, C. et al. Resistance pattern of human immunodeficiency virus type 1 reverse transcriptase to quinoxaline S-2720. J Virol 1994, 68(12): 7986-92.
26. Balzarini, J., Pelemans, H., Riess, G. et al. Zidovudine-resistant human immunodeficiency virus type 1 strains subcultured in the presence of both lamivudine and quinoxaline HBY 097 retain marked sensitivity to HBY 097 but not to lamivudine. J Infect Dis 1997, 176(5): 1392-7.
27. Balzarini, J., De Clercq, E., Carbonez, A. et al. 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(6): 517-28.
28. Corbett, J.W., Ko, S.S., Rodgers, J.D. et al. Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1. Antimicrob Agents Chemother 1999, 43(12): 2893-7.
29. Ahmad, A.R., Mehta, L.K., Parrick, J. Preparation of 3-substituted 6,7-dimethoxyquinoxalin-2(1H)-ones and studies of their potential as fluoroionophores. Tetrahedron 1995, 51(47): 12899-910.
30. Ries, U.J., Priepke, H.W.M., Hauel, N.H. et al. Heterocyclic thrombin inhibitors. Part 2: Quinoxalinone derivatives as novel, potent antithrombotic agents. Bioorg Med Chem Lett 2003, 13(14): 2297-302.
31. Ulrich, R.G., Bacon, J.A., Cramer, C.T. et al. Disruption of mitochondrial activities in rabbit and human hepatocytes by a quinoxalinone anxiolytic and its carboxylic acid metabolite. Toxicology 1998, 131(1): 33-47.