Synthesis and biological evaluation of N-acylhydrazones as inhibitors of MurC and MurD ligases

ChemMedChem

Volumn 3, Issue 9, 2008, Pages 1362-1370

  Šink, Roman ^a   Kovač, Andreja ^a   Tomašić, Tihomir ^a   Rupnik, Veronika ^a   Boniface, Audrey ^b   Bostock, Julieanne ^c   Chopra, Ian ^c   Blanot, Didier ^b   Mašič, Lucija Peterlin ^a   Gobec, Stanislav ^a   Zega, Anamarija ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b INSTITUTE FOR INTEGRATIVE BIOLOGY OF THE CELL I2BC   (France)

^c UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Antibacterial agents; Inhibitors; Mur ligases; N acylhydrazone

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; ENZYME INHIBITOR; HYDRAZONE DERIVATIVE; LIGASE; PEPTIDOGLYCAN;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; ESCHERICHIA COLI; MICROBIOLOGICAL EXAMINATION; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; ESCHERICHIA COLI; HYDRAZONES; LIGASES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDOGLYCAN; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 54849442053     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200800087     Document Type: Article

References (46)

1. P. Nordmann, T. Naas, Curr. Opin. Microbiol. 2007, 10, 436-440.
2. J. L. Marquardt, E. D. Brown, W. S. Lane, T. M. Haley, Y. Ichikawa, C. H. Wong, C. T. Walsh, Biochemistry 1994, 33, 10646-10 651.
3. J. van Heijenoort, Nat. Prod. Rep. 2001, 18, 503-519.
4. H. Barreteau, A. Kovač, A. Boniface, M. Sova, S. Gobec, D. Blanot, FEMS Microbiol. Rev. 2008, 32, 168-207.
5. a) F. Reck, S. Marmor, S. Fisher, M. A. Wuonola, Bioorg. Med. Chem. Lett. 2001, 11, 1451-1454;
6. b) M. E. Tanner, S. Vaganay, J. van Heijenoort, D. Blanot, J. Org. Chem. 1996, 61, 1756-1760;
7. c) L. D. Gegnas, S. T. Waddell, R. M. Chabin, S. Reddy, K. K. Wong, Bioorg. Med. Chem. Lett. 1998, 8, 1643-1648;
8. d) S. Gobec, U. Urleb, G. Auger, D. Blanot, Pharmazie 2001, 56, 295-297;
9. e) K. Strancar, D. Blanot, S. Gobec, Bioorg. Med. Chem. Lett. 2006, 16, 343-348;
10. f) J. Humljan, M. Kotnik, A. Boniface, T. Solmajer, U. Urleb, D. Blanot, S. Gobec, Tetrahedron 2006, 62, 10980-10988;
11. g) K. Strancar, A. Boniface, D. Blanot, S. Gobec, Arch. Pharm. 2007, 340, 127-134.
12. Z. Li, G. D. Francisco, W. Hu, P. Labthavikul, P. J. Petersen, A. Severin, G. Singh, Y. Yang, B. A. Rasmussen, Y-I Lin, J. S. Skotnicki, T. S. Mansour, Bioorg. Med. Chem. Lett. 2003, 13, 2591-2594.
13. M. M. Sim, S. B. Ng, A. D. Buss, S. C. Crasta, K. L. Goh, S. K. Lee, Bioorg. Med. Chem. Lett. 2002, 12, 697-699.
14. D. E. Ehmann, J. E. Demeritt, K. G. Hull, S. L. Fisher, Biochim. Biophys. Acta 2004, 1698, 167-174.
15. S. Antane, C. E. Caufield, W. Hu, D. Keeney, P. Labthavikul, K. Morris, S. M. Naughton, P. J. Petersen, B. A. Rasmussen, G. Singh, Y. Yang, Bioorg. Med. Chem. Lett. 2006, 16, 176-180.
16. J. R. Horton, J. M. Bostock, I. Chopra, L. Hesse, S. E. V. Phillips, D. J. Adams, A. P. Johnson, C. W. G. Fishwick, Bioorg. Med. Chem. Lett. 2003, 13, 1557-1560.
17. A. El Zoeiby, F. Sanschagrin, R. C. Levesque, Mol. Microbiol. 2003, 47, 1-12.
18. M. Kotnik, P. Štefanič Anderluh, A. Preželj, Curr. Pharm. Des. 2007, 13, 2283-2309.
19. M. Kotnik, J. Humljan, C. Contreras-Martel, M. Oblak, K. Kristan, M. HervS, D. Blanot, U. Urleb, S. Gobec, A. Dessen, T. Solmajer, J. Mol. Biol. 2007, 370, 107-115.
20. G. F. Stamper, K. L. Longenecker, E. H. Fry, C. G. Jakob, A. S. Florjancic, Y. Gu, D. D. Anderson, C. S. Cooper, T. Zhang, R. F. Clark, Y. Cia, C. L. Black-Schaefer, J. O. McCall, C. G. Lerner, P. J. Hajduk, B. A. Beutel, V. S. Stoll, Chem. Biol. Drug Des. 2006, 67, 58-65.
21. a) A. Gürsoy, N. Terzioglu, G. Ötük, Eur. J. Med. Chem. 1997, 32, 753-757;
22. b) E. Szarvasi, L. Fontaine, A. Betbeder-Matibet, J. Med. Chem. 1973, 16, 281-287;
23. c) H. M. Eisa, A. S. Tantawy, M. M. El-Kerdawy, Pharmazie 1991, 46, 182-184;
24. d) M. A. Khalil, O. A. El-Sayed, H. A. El-Shamy, Arch. Pharm. 1993, 326, 489-492;
25. e) N. Ulusoy, G. Çapan, G. Ötük, M. Kiraz, Boll. Chim. Farm. 2000, 139, 167-172;
26. f) N. Ulusoy, N. Ergenç, G. Ötük, M. Kiraz, Boll. Chim. Farm. 2001, 140, 417-421;
27. g) S. Rollas, N. GTlerman, H. Erdeniz, Farmaco 2002, 57, 171-175;
28. h) S. G. Küçükgüzel, E. E. Oruç, S. Rollas, F. Sahin, A. Özbek, Eur. J. Med. Chem. 2002, 37, 197-202;
29. i) K. A. Metwally, L. M. Abdel-Aziz, E. M. Lashine, M. I. Husseiny, R. H. Badawhy, Bioorg. Med. Chem. 2006, 14, 8675-8682.
30. C. D. Duarte, E. J. Barreiro, C. A. M. Fraga, Mini-Rev. Med. Chem. 2007, 7, 1108-1119.
31. G. Palla, G. Predieri, P. Domiano, Tetrahedron 1986, 42, 3649-3654.
32. SYBYL Molecular Modeling Software is available from Tripos Inc., 1699 S. Hanley Road, St. Louis, MO 63144-2913 (USA): http://www.tripos.com (last access: June 30, 2008).
33. a) D. Liger, A. Masson, D. Blanot, J. van Heijenoort, C. Parquet, Eur. J. Biochem. 1995, 230, 80-87;
34. b) G. Auger, L. Martin, J. Bertrand, P. Ferrari, E. Fanchon, S. Vaganay, Y. PStillot, J. van Heijenoort, D. Blanot, O. Dideberg, Protein Expression Purif. 1998, 13, 23-29.
35. P. A. Lanzetta, L. J. Alvarez, P. S. Reinach, O. Candia, Anal. Biochem. 1979, 100, 95-97.
36. S. L. McGovern, B. K. Shoichet, J. Med. Chem. 2003, 46, 1478-1483.
37. a) D. Liger, D. Blanot, J. van Heijenoort, FEMS Microbiol. Lett. 1991, 64, 111-115;
38. b) G. Auger, J. van Heijenoort, D. Blanot, C. Deprun, J. Prakt. Chem. 1995, 337, 351-357.
39. Gold v 3.2 is available from The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ (UK): http://www.ccdc.cam.ac.uk (last access: June 30, 2008).
40. PyMOL: http://pymol.sourceforge.net (last access: June 30, 2008).
41. E. R. Buchman, E. M. Richardson, J. Am. Chem. Soc. 1939, 61, 891-893.
42. G. E. Hall, J. Chem. Soc. 1966, 6, 1357-1360.
43. H. Ding, G. K. Friestad, Synthesis 2004, 2216-2221.
44. S. Rostamizadeh, S. A. Ghasem Housaini, Tetrahedron Lett. 2004, 45, 8753-8756.
45. M. Clark, R. D. Cramer III, N. Van Opdenbosch, J. Comput. Chem. 1989, 10, 982-1012.
46. M. J. D. Powell, Math. Prog. 1977, 12, 241-254.