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Synthesis and Antimicrobial Activities of Some New Nitroimidazole Derivatives  

Benkli, Kadriye (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
Karaburun, Ahmet-Cagrl (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
Gundogdu-Karaburun, Nalan (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
Demirayak, Seref (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
Guven, Klymet (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Anadolu)
Publication Information
Archives of Pharmacal Research / v.26, no.10, 2003 , pp. 773-777 More about this Journal
Abstract
In this study, some new nitroimidazole derivatives were obtained from 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylamine dihydrochloride (4) and 1-(2-bromoethyl)-2-methyl-5-nitroimidazole (5), which were prepared using metronidazole. Compound 4 was reacted with arylisothiocyanates (6) to obtain 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-3-arylthioureas (7) and the latter with $\alpha$-bromoacetophenones (8) to give -3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-arylimino-4-aryl-4-thiazolines (9). Also 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-phenyl-4-arylideneimidazolin-5-ones (11) were prepared by reaction of 4 with 2-phenyl-4-arylidene-5-oxazolones (10). The reaction of the other starting material 5 with 5-arylidenethiazolidin-2,4-dione (12) gave 3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-5-arylidenethiazolidin-2,4-dione (13) derivatives. Structural elucidation of the compounds was performed by IR, $^1H-NMR$ and MASS spectroscopic data and elemental analysis results. Antimicrobial activities of the compounds were examined and moderate activity was obtained.
Keywords
Metronidazole; Nitroimidazoles; Antibacterial and antifungal activity;
Citations & Related Records

Times Cited By Web Of Science : 4  (Related Records In Web of Science)
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1 Carganico, G. and Cozzi, P., Imidazolyl derivatives in medicinal chemistry. Farmaco, 46, 209-231 (1991)   PUBMED
2 Demirayak, S. and Kiraz, N., Some nitroimidazole derivatives as possible antibacterial agents. Farmaco, 48, 443-446 (1993)   PUBMED
3 Griffin, S., Woods, T. S., and Klayman, D. L., Thioureas in the synthesis of heterocycles. Adv. Heterocyclic Chem., 18, 99-158 (1974)
4 Lima, M. C. A., Costa, D. L. B., Goes, A. J. S., Galdino, S. L., Pitta, I. R., and Luu-Duc, C., Synth$\grave{e}$se et activit$\acute{e}$ antimicrobienne de d$\acute{e}$riv$\grave{e}$s chlorobenzyl benzylid$\grave{e}$ne imidazolidinediones et thiazolidinediones substitu$\acute{e}$es. Pharmazie, 47, 182-184 (1992)   PUBMED
5 Turan-Zitouni, G., Sivaci, D. M., KaplancIklI, Z. A., and Ozdemir, A., Synthesis and antimicrobial activity of some pyridinyliminothiazoline derivatives. Farmaco, 57, 569-572 (2002)   DOI   ScienceOn
6 Tovarna Zdravil, K. R. K. A., 1-(2-Bromoethyl)-2-methyl-5-nitroimidazole from the 1-(2-hydroxyethyl) analog, Fr. 1,540,545, C.A. 71, 81362k (1969)
7 Patel, P. H., Korgaokar, S. S., and Parekh, H. H., Synthesis and antimicrobial activity of 4-thiazolidinone and imidazolinone derivatives bearing a 2-aminothiazole moiety. Indian J. Heterocycl. Chem., 7, 73-76 (1997)
8 Finegold, S. M., Martin, W. J., and Scott E. G., Bailey and Scotts Diagnostic Microbiology; The C.V. Mosby Company, Saint Louis (1978)
9 Demirayak, S., Karaburun, A. C., and Kiraz, N., Synthesis and antibacterial activities of some 1-[2-(substituted pyrrol-1-yl)ethyl]-2-methyl-5-nitroimidazole derivatives. Eur. J. Med. Chem., 34, 275-278 (1999)   DOI   ScienceOn
10 Hanna, M. M., Abbas, SE-S., Mogahazy Aly, S. M., Megid, R. M. A., and Moustafa, M. M., Synthesis and antimicrobial activity of some substituted 3-aryl-5-benzylidene-2-phenyl-4-imidazolone derivatives. Bull. Fac. Pharm. Cairo Univ., 32, 353-358 (1994)
11 Mahfouz, N. M., Aboul-Fadl, T., and Diab, A. K., Metronidazole twin ester prodrugs; synthesis, physicochemical properties, hydrolysis kinetics and antigiardial activity. Eur. J. Med. Chem., 33, 675-683 (1998)   DOI   ScienceOn
12 Cawper, R. N. and Davidson, L. H., a-Bromo acetophenone. Org. Syn. Coll., 2, 480 (1943)
13 Wolf, M. E., Burgers Medicinal Chemistry and Drug Discovery, 5th ed., John Wiley and Sons, New York, Vol. 4, pp 429-452 (1997)
14 Allimony, H. A., Saad, H. A., and Mariah, F. A. A., Synthesis and antimicrobial activity of some nitrogen heterobicyclic systems: Part I. Indian J. Chem. Sec. B, 38, 445-451 (1999)
15 Mc Ginnis, M. R. and Rinaldi. M. G., Antifungal drugs; Mechanism of action, drug resistance, susceptibility testing and assays of activity in biological fluids, Ed. V. Lorian, Antibiotics in Laboratory Medicine Third Ed., Williams and Wilkins, London, Los Angeles, 198 (1991)
16 Silverstein, R. M., Bassler, G. C., and Morrill, T. C., Spectrometric identification of organic compounds, 5th ed., John Wiley and Sons (1991)
17 Turcki, I. J., Oxazoles, The Chemistry of heterocyclic compounds, Weisberger, A., Taylor, E.C., John Wiley and Sons (1986)
18 Bowden, K. and Izadi, J., Multifunctional derivatives of metronidazole. Farmaco, 53, 58-61(1998)   DOI   ScienceOn
19 Mahfouz, N. M. and Hasan, M. A., Synthesis, chemical and enzymatic hydrolysis, and bioavailability evaluation in rabbits of metronidazole amino acid ester prodrugs with enhanced water solubility. J. Pharm. Pharmacol., 53, 841-848 (2001)   DOI   ScienceOn