4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 13, 2011, Pages 3884-3891

  Xiao, Zhu Ping ^a,b   Ouyang, Hui ^a   Wang, Xu Dong ^a   Lv, Peng Cheng ^b   Huang, Ze Jun ^a   Yu, She Rong ^a   Yi, Tian Fang ^a   Yang, Ye Ling ^a   Zhu, Hai Liang ^a,b  

^a JISHOU UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Antibacterial; Furanone; Molecular docking; Structure activity relationship; Tyrosyl tRNA synthetase

Indexed keywords

3 (3 BROMOPHENYL) 4 (2 MORPHOLINOETHOXY)FURAN 2(5H) ONE; 3 (3 CHLOROPHENYL) 4 (2 MORPHOLINOETHOXY)FURAN 2(5H) ONE; 3 (3,4 DICHLOROPHENYL) 4 [2 (4 METHYLPIPERAZIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 3 (3,4 DIFLUOROPHENYL) 4 [2 (PIPERIDIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 3 (3,4 DIMETHOXYPHENYL) 4 [2 (4 METHYLPIPERAZIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 3 (3,4 DIMETHOXYPHENYL) 4 [2 (PIPERIDIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 3 (4 CHLOROPHENYL) 4 (2 MORPHOLINOETHOXY)FURAN 2(5H) ONE; 3 (4 HYDROXYPHENYL) 4 (2 MORPHOLINOETHOXY)FURAN 2(5H) ONE; 3 ARYL 4 AMINOFURAN 2(5H) ONE; 3 PHENYL 4 [2 (PIPERIDIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 3 PHENYL 4 [2 (PROPYLAMINO)ETHOXY]FURAN 2(5H) ONE; 3 PHENYL 4 [2 (PYRROLIDIN 1 YL)ETHOXY]FURAN 2(5H) ONE; 4 (2 MORPHOLINOETHOXY) 3 PHENYLFURAN 2(5H) ONE; 4 [2 (4 METHYLPIPERAZIN 1 YL)ETHOXY] 3 PHENYLFURAN 2(5H) ONE; 4 [2 (BENZYLAMINO)ETHOXY] 3 PHENYLFURAN 2(5H) ONE; 4 [2 (BUTYLAMINO)ETHOXY] 3 PHENYLFURAN 2(5H) ONE; 4 [2 (CYCLOHEXYLAMINO)ETHOXY] 3 (3,4 DIMETHOXYPHENYL)FURAN 2(5H) ONE; 4 [2 (CYCLOHEXYLAMINO)ETHOXY] 3 PHENYLFURAN 2(5H) ONE; 4 [2 [2 (4 NITROPHENYL)HYDRAZINYL]ETHOXY] 3 PHENYLFURAN 2(5H) ONE; 4 ALKOXY 3 ARYLFURAN 2(5H) ONE DERIVATIVE; 5 ALKOXY 4 AMINOFURAN 2(5H) ONE; 5 FLUORO 1,3 DIHYDRO 2,1 BENZOXABOROL 1 OL; ANTIINFECTIVE AGENT; BUTALACTIN; ICOFUNGIPEN; KANAMYCIN; KETOCONAZOLE; PENICILLIN G; TYROSINE TRANSFER RNA LIGASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HYDROPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

4-BUTYROLACTONE; ANTI-BACTERIAL AGENTS; BINDING SITES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; FURANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MORPHOLINES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE-TRNA LIGASE;

POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 79959505902     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.05.042     Document Type: Article

References (22)

1. X. Qiu, C.A. Janson, W.W. Smith, S.M. Green, P. McDevitt, K. Johanson, P. Carter, M. Hibbs, C. Lewis, A. Chalker, A. Fosberry, J. Lalonde, J. Berge, P. Brown, C.S. Houge-Frydrych, and R.L. Jarvest Protein Sci. 10 2001 2008
2. S.G. Park, P. Schimmel, and S. Kim Proc. Natl. Acad. Sci. 105 2008 11043
3. P. Van de Vijver, G.H.M. Vondenhoff, T.S. Kazakov, E. Semenova, K. Kuznedelov, A. Metlitskaya, A. Van Aerschot, and K. Severinov J. Bacteriol. 191 2009 6273
4. R. Farhanullah, T. Kang, E.-J. Yoon, E.-C. Choi, S. Kim, and J. Lee Eur. J. Med. Chem. 44 2009 239
5. M. Hoffmann, and M. Torchala J. Mol. Model. 15 2009 665
6. C. Balg, M. De Mieri, J.L. Huot, S.P. Blais, J. Lapointe, and R. Chênevert Bioorg. Med. Chem. 18 2010 7868
7. P. Van de Vijver, T. Ostrowski, B. Sproat, J. Goebels, O. Rutgeerts, A. Van Aerschot, M. Waer, and P. Herdewijn J. Med. Chem. 51 2008 3020
8. P. Van de Vijver, G.H.M. Vondenhoff, S. Denivelle, J. Rozenski, J. Verhaegen, A. Van Aerschot, and P. Herdewijn Bioorg. Med. Chem. 17 2009 260
9. V. Weber, C. Rubat, E. Duroux, C. Lartigue, M. Madesclaire, and P. Coudert Bioorg. Med. Chem. 13 2005 4552
10. D.K. Black J. Chem. Soc. 23 1966 1123
11. F. Bailly, C. Quefflec, G. Mbemba, J.F. Mouscadet, N. Pommery, J. Pommery, J.P. Hnichart, and P. Cotelle Eur. J. Med. Chem. 43 2008 1222
12. E. Lattmann, S. Dunn, S. Niamsanit, and N. Sattayasai Bioorg. Med. Chem. Lett. 15 2005 919
13. T. Ueki, and T. Kinoshita Org. Biomol. Chem. 2 2004 2777
14. E. Lattmann, N. Sattayasai, C.S. Schwalbe, S. Niamsanit, and D.C. Billington Curr. Drug Discovery Technol. 3 2006 125
15. Z.-P. Xiao, J.-Y. Xue, S.-H. Tan, H.-Q. Li, and H.-L. Zhu Bioorg. Med. Chem. 15 2007 4212
16. Z.-P. Xiao, R.-Q. Fang, H.-Q. Li, J.-Y. Xue, Y. Zheng, and H.-L. Zhu Eur. J. Med. Chem. 43 2008 1828
17. Z.-P. Xiao, X.-B. He, Z.-Y. Peng, T.-J. Xiong, J. Peng, L.-H. Chen, and H.-L. Zhu Bioorg. Med. Chem. 19 2011 1571
18. Z.-P. Xiao, J. Zhu, W. Jiang, G.-X. Li, and X.-D.Z. Wang Kristallogr. NCS 225 2010 797
19. T. Fujihara, Y. Katafuchi, T. Iwai, J. Terao, and Y. Tsuji J. Am. Chem. Soc. 132 2010 2094
20. Z.-P. Xiao, W.-B. Yan, Z.-X. Liu, L.-H. Chen, and X.-C. Peng Acta Cryst. E66 2010 o3068
21. C.C. Chiou, N. Mavrogiorgos, E. Tillem, R. Hector, and T. Walsh J. Antimicrob. Agents Ch. 45 2001 3310
22. G.M. Sheldrick SHELXTL-97, Program For Crystal Structure Solution and Refinement 1997 University of Göttingen Göttingen, Germany