Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2 H)-benzofuranone derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 22, 2007, Pages 6354-6363

  Hadj esfandiari, Narges ^a   Navidpour, Latifeh ^a   Shadnia, Hooman ^b   Amini, Mohsen ^a   Samadi, Nasrin ^a   Faramarzi, Mohammad Ali ^c   Shafiee, Abbas ^a  

^a Tehran University of Medical Sciences   (Iran)

^b CARLETON UNIVERSITY   (Canada)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

3(2 H) Benzofuranone; Antibacterial; Nitroimidazole; QSAR

Indexed keywords

2 (1 METHYL 4 NITROIMIDAZOLE 5 YLMETHYLENE) 3(2H) BENZOFURANONE; 2 (NITROIMIDAZOLYLMETHYLENE) 3(2H) BENZOFURANONE; AMOXICILLIN; BENZOFURAN DERIVATIVE; CARBENE; NITROIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

ANTI-BACTERIAL AGENTS; BACTERIA; BENZOFURANS; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

BACILLUS SUBTILIS; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 35148820603     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.062     Document Type: Article

References (31)

1. Public Health Laboratory Service. Commun. Dis. Rep. 2001, 11, 7.
2. Low D.E., Keller N., Barth A., and Jones R.N. Clin. Infect. Dis. 32 (2001) S133
3. Edwards, D. I. DNA-Binding and Nicking Agents. In Enzymes and other Molecular Targets; Sammes, P. G., Taylor, J. B., Eds.; Comprehensive Medicinal Chemistry. The Rational Design, Mechanistic Study & Therapeutic Application of Chemical Compounds; Hansch, C., Ed.; Pergamon Press: Oxford, 1990; Vol. 2, pp 725-751.
4. Edwards D.I. J. Antimicrob. Chemother. 31 (1993) 9
5. Knight R.C., Skolimowski I.M., and Edwards D.I. Biochem. Pharmacol. 27 (1978) 2089
6. Pires J.R., Saito C., Gomes S.L., Giesbrecht A.M., and Amaral A.T. J. Med. Chem. 44 (2001) 3673
7. Thomas M.G., Lawson C., Allanson N.M., Leslie B.W., Bottomley J.R., McBride A., and Olusanya O.A. Bioorg. Med. Chem. Lett. 13 (2003) 423
8. Foroumadi A., Ghodsi S., Emami S., Najjari S., Samadi N., Faramarzi M.A., Beikmohammadi L., Shirazi F.H., and Shafiee A. Bioorg. Med. Chem. Lett. 16 (2006) 3499
9. Foroumadi A., Oboudiat M., Emami S., Karimollah A., Saghaee L., Moshafi M.H., and Shafiee A. Bioorg. Med. Chem. 14 (2006) 3421
10. Foroumadi A., Emami S., Hassanzadeh A., Rajaee M., Sokhanvar K., Moshafi M.H., and Shafiee A. Bioorg. Med. Chem. Lett. 15 (2006) 4488
11. Foroumadi A., Emami S., Mehni M., Moshafi M.H., and Shafiee A. Bioorg. Med. Chem. Lett. 15 (2005) 4536
12. Foroumadi A., Pournourmohammadi S., Soltani F., Asgharian-Rezaee M., Dabiri S., Kharazmi A., and Shafiee A. Bioorg. Med. Chem. Lett. 15 (2005) 1983
13. Tehranchian S., Akbarzadeh T., Fazeli M.R., Jamalifar H., and Shafiee A. Bioorg. Med. Chem. Lett. 15 (2005) 1023
14. Edwards C.R., Readhead M.J., and Tweddle N.J. J. Het. Chem. 24 (1987) 495
15. Robertson A. J. Chem. Soc. (1932) 1389
16. Carvalho C.F., and Sargebt M.V. J. Chem. Soc., Perkin Trans. 1 (1984) 1605
17. Rufer C., Kessler H.-J., Schröder E., and Damerius A. Chim. Ther. 7 (1972) 5
18. 4: C, 57.57; H, 3.34; N, 15.49. Found: C, 57.71; H, 3.47; N, 15.30.
19. Varma R.S., and Varma M. Tetrahedron Lett. 33 (1992) 5937
20. MOE. Chemical Computing Group Inc., Montreal, Quebec, Canada, 2006, see http://www.chemcomp.com.
21. Halgren T.A. J. Comp. Chem. 20 (1999) 720
22. Halgren T.A. J. Comp. Chem. 20 (1999) 730
23. Bashford D., and Case D. Annu. Rev. Phys. Chem. 51 (2000) 129
24. Hall L.H., and Kier L.B. Rev. Comp. Chem. (1991) 2
25. Ertl P., Rohde B., and Selzer P. J. Med. Chem. 43 (2000) 3714
26. Wildman S.A., and Crippen G.M. J. Chem. Inf. Comput. Sci. 5 (1999) 868
27. Labute P. Pac. Symp. Biocomput. 4 (1999) 444
28. Baron, E. J.; Finegolg, S. M.; In Baily and Scott's Diagnostic Microbiology, 8th ed.; Mosby, C. V., St. Louis, 1990; pp 184-188.
29. The antibacterial properties of 11o-p which were oxidizable were performed in the presence of BHT 0.1% as an antioxidant. The antibacterial activity of BHT 0.1% was evaluated and no activity against any of the tested bacteria was observed.
30. The Gram-negative bacteria utilized in this study consisted of Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027, and Klebsiella pneumoniae ATCC 10031.
31. Stanton D., and Jurs P. Anal. Chem. 62 (1990) 2323