Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 5, 2013, Pages 1274-1278

  Bahnous, Mebarek ^a   Bouraiou, Abdelmalek ^a   Chelghoum, Meryem ^a   Bouacida, Sofiane ^a   Roisnel, Thierry ^b   Smati, Farida ^c   Bentchouala, Chafia ^c   Gros, Philippe C ^d   Belfaitah, Ali ^a  

^a Universite Mentouri Constantine   (Algeria)

^b UNIVERSITÉ DE RENNES 1   (France)

^c Centre Hospitalo Universitaire Dr Benbadis Constantine   (Algeria)

^d UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Antibacterial activity; Crystal structure; Halogenation; Haloimidazole; Imidazolium salt; Nitroimidazole

Indexed keywords

1 METHYLIMIDAZOLE; 2 PHENYL 1 METHYLIMIDAZOLE; ANTIBIOTIC AGENT; IMIDAZOLE; IMIDAZOLE DERIVATIVE; ION; SPIRAMYCIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; CRYSTAL STRUCTURE; DISK DIFFUSION; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

ESCHERICHIA COLI; PSEUDOMONAS AERUGINOSA; SALMONELLA; STAPHYLOCOCCUS AUREUS;

EID: 84873707979     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.01.004     Document Type: Article

References (35)

1. D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi, and M. Botta Bioorg. Med. Chem. 17 2009 5716
2. E.J. Iwanowicz, S.H. Watterson, J. Guo, W.J. Pitts, T.G. Murali Dhar, Z. Shen, P. Chen, H.H. Gu, C.A. Fleener, K.A. Rouleau, D.L. Cheney, R.M. Townsend, and D.L. Hollenbaugh Bioorg. Med. Chem. Lett. 13 2003 2059
3. S.S. Kargaokar, P.H. Patil, M.T. Shah, and H.H. Parekh Indian J. Pharm. Sci. 58 1996 222
4. S.K. Pandey, A. Singh, and A.S. Nizamuddin Eur. J. Med. Chem. 44 2009 1188
5. A.H. Nasser Molecules 5 2000 826
6. G.W. Rao, and W.X. Hu Bioorg. Med. Chem. Lett. 15 2005 3174
7. M.M. Ali, M.F. Ismail, M.S.A. El-Gaby, M.A. Zahran, and Y.A. Ammar Molecules 5 2000 864
8. CIBA Ltd., Neth. Appl. 1965, 6412, 310; Chem. Abstr. 1965, 63, 11573c-d.
9. Lombardino, J. G. Ger. Offen. 1972, 2155, 558; Chem. Abstr. 1972, 77, 101607y.
10. J.G. Lombardino, and E.H. Wiseman J. Med. Chem. 17 1974 1182
11. B. Cui, B.L. Zheng, K. He, and Q.Y. Zheng J. Nat. Prod. 66 2003 1101
12. B. Fazeny-Dorner, M. Veitl, C. Wenzel, M. Piribauer, K. Rossler, K. Dieckmann, K. Ungersbock, and C. Marosi Anticancer Drugs 14 2003 437
13. P. Haluska, G.K. Dy, and A.A. Adjei Eur. J. Cancer. 38 2002 1685
14. E. Kotteas, C. Alamara, M. Kiagia, K. Pantazopoulos, A. Boufas, A. Provata, A. Charpidou, and K.N. Syrigos Anticancer Res. 28 2008 529
15. J.J. Perez-Ruixo, V. Piotrovskij, S. Zhang, S. Hayes, P. DePorre, and Br. P. Zannikos J. Clin. Pharmacol. 62 2006 81
16. I. Krezel Farmaco 53 1998 342
17. S.J. Dominianni, S.J. Dominianni, and Terence T. Yen J. Med. Chem. 32 1989 2301
18. E.V. Aleksandrova, A.N. Kravchenko, and P.M. Kochergin Chem. Heterocycl. Compd. 46 2011 1295
19. M.D. Mashkovskii Drugs [in Russian] 2005 Novaya Volna Moscow p 444
20. Ogawa M. Nishimura, A. Eur. Pat. Application No. 1417887, Ref. Zh. Khim., 2004, 04.18-190.271P.
21. P. Vanelle, J. Maldonado, M.P. Crozet, B. Savornin, F. Delmas, L. Gasquet, and P. Timon-David Eur. J. Med. Chem. 27 1992 551
22. M. Bahnous, C. Mouats, Y. Fort, and P.C. Gros Tetrahedron Lett. 47 2006 1949
23. M. Hoffer, V. Toome, and A. Brossi J. Heterocycl. Chem. 3 1966 454
24. S.K. Mal, L. Bohé, and S. Achab Tetrahedron 64 2008 5904
25. A. Foroumadi, S. Emami, S. Pournour mohammadi, A. Kharazmi, and A. Shafiee Eur. J. Med. Chem. 40 2005 1346
26. B. Letafat, S. Emami, A. Aliabadi, N. Mohammadhosseini, M.H. Moshafi, A. Asadipour, A. Shafiee, and A. Foroumadi Arch. Pharm. Chem. Life Sci. 341 2008 497
27. B. Boduszek, T.K. Olszewski, W. Goldeman, K. Grzegolec, and P. Blazejewska Tetrahedron 68 2012 1223
28. P. Vanelle, O. Jentzer, M. Bahnous, and M.P. Crozet Tetrahedron Lett. 29 1988 5361
29. 2 using SHELXL. Hydrogen atoms were refined on the riding model with isotropic thermal parameters set twenty percent greater than those of their bonding partners. All other atoms were refined anisotropically. Crystallographic data (excluding structure factors) for compounds 11b, 9a, 9b, 9c, 9d and 9f have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 901893 for 11b, CCDC 901892 for 9a, CCDC 901891 for 9b, CCDC 901896 for 9c, CCDC 901895 for 9d, and CCDC 901894 for 9f. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif./cif.
30. T. Kamenecka, J. Habel, D. Duckett, W. Chen, Y.Y. Ling, B. Frackowiak, R. Jiang, Y. Shin, X. Song, and P. LoGrasso J. Biol. Chem. 284 2009 12853
31. J. Chin, M. Drouin, and A.G. Michel Acta Crystallogr., Sect. C 46 1990 1022
32. D.J. Bennett, E.L. Carswell, A.J. Cooke, A.S. Edwards, and O. Nimz Curr. Med. Chem. 15 2008 195
33. D. Demberelnyamba, K.S. Kim, S. Choi, S.Y. Park, H. Lee, C.J. Kim, and I.D. Yoo Bioorg. Med. Chem. 12 2004 853
34. J. Pernak, I. Goc, and I. Mirska Green Chem. 6 2004 323
35. Couvalin, P.; Leclerc, R.; Bingen, E. Antibiogramme, 2nd ed.; Eds. ESKA: France, 1985.