Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 18, 2011, Pages 5403-5407

  Andaloussi, Mounir ^a   Lindh, Martin ^a   Björkelid, Christofer ^b   Suresh, Surisetti ^a   Wieckowska, Anna ^a   Iyer, Harini ^c   Karlén, Anders ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

^c ASTRAZENECA   (United Kingdom)

Author keywords

DXR; Enzyme inhibitor; Fosmidomycin; FR900098; Tuberculosis

Indexed keywords

1 DEOXY D XYLULOSE 5 PHOSPHATE REDUCTOISOMERASE; 3 (N ACETYL N HYDROXYAMINO)PROPYLPHOSPHONIC ACID; ANTIBIOTIC AGENT; FOSMIDOMYCIN; HYDROXAMIC ACID; OXIDOREDUCTASE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; SUBSTITUTION REACTION;

ALDOSE-KETOSE ISOMERASES; ANTITUBERCULAR AGENTS; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; FOSFOMYCIN; HYDROXAMIC ACIDS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MULTIENZYME COMPLEXES; MYCOBACTERIUM TUBERCULOSIS; OXIDOREDUCTASES; PHOSPHONIC ACIDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MYCOBACTERIUM TUBERCULOSIS;

EID: 80051925129     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.07.005     Document Type: Article

References (25)

1. http://www.who.org.
2. Y. Shigi J. Antimicrob. Chemother. 24 1989 131
3. L.M. Henriksson, T. Unge, J. Carlsson, J. Aqvist, S.L. Mowbray, and T.A. Jones J. Biol. Chem. 282 2007 19905
4. A.C. Brown, and T. Parish BMC Microbiol. 2008 8
5. J. Perruchon, R. Ortmann, M. Altenkamper, K. Silber, J. Wiesner, H. Jomaa, G. Klebe, and M. Schlitzer ChemMedChem 3 2008 1232
6. C. Zinglé, L. Kuntz, D. Tritsch, C. Grosdemange-Billiard, and M. Rohmer J. Org. Chem. 75 2010 3203
7. L.S. Deng, S. Sundriyal, V. Rubio, Z.Z. Shi, and Y.C. Song J. Med. Chem. 52 2009 6539
8. T. Haemers, J. Wiesner, D. Gießmann, T. Verbrugghen, U. Hillaert, R. Ortmann, H. Jomaa, A. Link, M. Schlitzer, and S. Van Calenbergh Bioorg. Med. Chem. 16 2008 3361
9. K. Blazewska, and T. Gajda Tetrahedron 59 2003 10249
10. J. Perruchon, R. Ortmann, and M. Schlitzer Synthesis 2007 3553
11. M. Larhed, C. Moberg, and A. Hallberg Acc. Chem. Res. 35 2002 717
12. R. Gaudry Can. J. Chem. 29 1951 544
13. D.R. Hou, J.H. Reibenspies, and K. Burgess J. Org. Chem. 66 2001 206
14. Z. Mincheva, M. Courtois, F. Andreu, M. Rideau, and M.C. Viaud-Massuard Phytochemistry 66 2005 1797
15. P. Nilsson, K. Olofsson, and M. Larhed Top. Curr. Chem. 266 2006 103
16. D. Noteberg, W. Schaal, E. Hamelink, L. Vrang, and M. Larhed J. Comb. Chem. 5 2003 456
17. J. Wannberg, D. Dallinger, C.O. Kappe, and M. Larhed J. Comb. Chem. 7 2005 574
18. D.J. Burkhart, A.R. McKenzie, J.K. Nelson, K.I. Myers, X. Zhao, K.R. Magnusson, and N.R. Natale Org. Lett. 6 2004 1285
19. G.K. Datta, H. von Schenck, A. Hallberg, and M. Larhed J. Org. Chem. 71 2006 3896
20. M. Harmata, K.-o. Rayanil, V.R. Espejo, and C.L. Barnes J. Org. Chem. 74 2009 3214
21. Schrödinger LCC: New York, NY, 2009.
22. M. Andaloussi, L.M. Henriksson, A. Wickowska, M. Lindh, C. Björkelid, A.M. Larsson, S. Suresh, H. Iyer, B.R. Srinivasa, T. Bergfors, T. Unge, S.L. Mowbray, M. Larhed, T.A. Jones, and A. Karlén J. Med. Chem. 54 2011 4964
23. L. Deng, J. Diao, P. Chen, V. Pujari, Y. Yao, G. Cheng, D.C. Crick, B.V.V. Prasad, and Y. Song J. Med. Chem. 54 2011 4721
24. T. Kuzuyama, S. Takahashi, H. Watanabe, and H. Seto Tetrahedron Lett. 39 1998 4509
25. 50-values presented are the average value of three independent experiments.