Some nitroimidazole derivatives as antibacterial and antifungal agents in in vitro study
DOI:
https://doi.org/10.20883/jms.218Keywords:
nitroimidazoles, nitroimidazooxazoles, nitroimidazotetrahydropyrimidines, M. tuberculosis, antifungalsAbstract
Nitroimidazoles have wide range of therapeutic uses mainly as anaerobic antibacterials and antiprotozoal agents. Some bicyclic nitroimidazodihydrooxazoles and nitroimidazotetrahydrooxazines are found to be antituberculosis agents. Hence, the biological and chemical properties of mentioned substances are of great interest to scientists. The aim of this review is to show the general knowledge concerning the chemistry and biological activity of some nitroimidazole derivatives, based on experimental studies. The results of biological tests provide many useful information on the effects of particular groups or other structural elements on the level of pharmacological activity. Also, these studies can be helpful in further planning of syntheses of active substances with using nitroimidazole moiety.
Downloads
References
Mital A. Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships. Sci Pharm. 2009 Aug;77:497–520.
Mukherjee T, Boshoff H. Nitroimidazoles for the treatment of TB: past, present and future. Future Med Chem. 2011 Nov;3(11):1427–1454.
Boyer JH. Nitroazoles. VCH Publishers Inc, Florida. 1986,165–166.
Clifton EB, Boshoff HIM, Dowd CF. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr Pharm Design. 2004 Oct;10:3239–3262.
Adib M, Sheibani E, Mostofi M, Ghanbary K, Bijanzadeh HR. Efficient highly diastereoselective synthesis of 1,8a‑dihydro-7H‑imidazo[2,1-b][1,3]oxazines. Tetrahedron. 2006 Apr; 62:3435–3438.
Agrawal KC, Bears K, Sehgal RK, Brown JN, Rist PE, Rupp WD. Potential radiosensitizing agents. Nitroimidazoles. J Med Chem. 1979;22:583–586.
Nagarajan K, Shankar R, Rajappa S, Shenoy ST, Costa‑Pereira R. Nitroimidazoles XXI. 2,3-dihydro-6-nitroimidazo[2,1-b]oxazoles with antitubercular activity. Eur J Med Chem. 1989;24:631–633.
Otera J, Orita A. US Patent No. 7, 115, 736 B2 (2006).
Żwawiak J, Olender D, Zwolska Z, Augustynowicz‑Kopeć E, Zaprutko L. Synthesis of 2,3-dihydro-7-nitroimidazo[5,1-b]oxazoles as potential tuberculostatic agents. Acta Pol Pharm. 2008 Apr;65:229–233.
Nemukhin AV, Grigorenko BI, Granovsky AA. Molecular modeling by using the PC GAMESS program: From diatomic molecules to enzymes. Moscow University Chemistry Bulletin. 2004;45,75–102.
Thompson AM, Blaser A, Anderson RF, Shinde SS, Franzblau SG, Ma Z et al. Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H‑imi-dazo[2,1-b][1,3]oxazine (PA-824). J Med Chem. 2009 Feb;52:637–645.
Bhaumik K, Akamanchi KG. 2,4-Dinitroimidazole: Microwave assisted synthesis and use in synthesis of 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole analogues with antimycobacterial activity. J Heterocyclic Chem. 2004 Jan;41:51–55.
Denny WA. TBA-354: A new drug for the treatment of persistent tuberculosis. Chemistry in New Zealand 2015;January:18–22.
Kim P, Zhang L, Manjunatha UH, Singh R, Patel S, Jiricek J et al. Structure‑activity relationships of antitubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles. J Med Chem. 2009 Mar;52:1317–1328.
Kim P, Kang S, Boshoff HI, Jiricek J, Collins M, Singh R et al. Structure‑activity relationships of antitubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure‑activity relationships. J Med Chem. 2009 Mar;52:1329–1344.
Zaprutko L, Żwawiak J, Zwolska Z, Augustynowicz‑Kopeć E, Bartoszak‑Adamska E, Nowicki W. Synthesis, structure and biological evaluation of novel bicyclic nitroimidazole derivatives. Arch Pharm Chem Life Sci. 2012 Dec;345:463–467.
Żwawiak J, Kujawski J, Zaprutko L. Structure — tuberculostatic activity evaluation among isomeric bicyclic nitroimidazoles. Acta Pol Pharm. 2017; in press.
Żwawiak J, Gzella A, Zaprutko L. Reactions of nitroimidazodihydrooxazole with alcohols and phenols in the presence of potassium carbonate. Pol J Chem. 2009 Mar;83:1309–1315.
Żwawiak J, Perdoch W, Mazela B, Zaprutko L. Synthesis and antifungal properties of some nitroimidazole derivatives. Int J Med Pharm Res. 2014 Aug;2:622–633.
Olender D, Żwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, Zaprutko L. Synthesis of some N‑substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. Eur J Med Chem. 2009 May;44:645–652.
Tułecki J, Zaprutko L. Synteza związków pochodnych 2-propanolu z układem nitroimidazolu. Acta Pol Pharm. 1984;3:281–292.
Downloads
Published
Issue
Section
License
Copyright (c) 2019 Justyna Żwawiak, Dorota Olender, Lucjusz Zaprutko
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.