Document Type: Research(Original) Article
Basic Sciences in Infectious Diseases Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
Department of Parasitology and Mycology, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
Nitroimidazole derivatives such as Metronidazole (MTZ) have been used as anti- protozoa and anti-anaerobic bacteria. In this study several compounds of MTZ derivatives were synthesized and evaluated against Giardia lamblia cyst. Firs MTZ were reacted with several alkyl halide to obtain O-alkyl MTZ derivatives, then products were purified and their chemical structures were confirmed by elemental and spectral analysis (1HNMR and Mass). In order to biological evaluation all compounds were investigated against 25 Giardia samples isolated from giarfdiasis patients. Results showed compound 2a had the most activity on cyst of Giardia in comparison with MTZ.
- - Scorza AV, Lappin M R. Metronidazole for the treatment of feline giardiasis. J Feline Medicine & Surgery 2004; 6: 157-160.
- - Turner ML, Cockerell EJ, Brereton HM, Badenoch PR, Tea M, Coster DJ, Williams KA.
- Antigens of selected Acanthamoeba species detected with monoclonal antibodies. Int J
- Parasitol 2005; 35: 981-90.
- -Karabay O, Tamer A, Gunduz H, Kayas D, Arinc H, Celebi H. Albendazole versus metronidazole treatment of adult giardiasis: an open randomized clinical study. World J Gastroentrol 2004; 10: 1215-7.
- - Adam RD. The biology of Giardia spp. Microbiol Rev 1991; 55: 706-32.
- - Anthwal Amit; Rawat D.S.; Rawat M.S.M. 5-Nitroimidazole derivatives: A scope of Modification for Medicinal chemists. Res. J. Chem. Sci.. Vol. 3(7), 104-113, July (2013)
- - Cava T, Gozukara SE. Genotoxicity evaluation of metronidazole using the piscine micronucleus test by acridine orange fluorescent staining. Environmental Toxicology and Pharmacology 2005; 19: 107-111.
- - Bharti N, Athar F, Maurya MR, Azam A. Synthesis, characterization and in vitro anti-amoebic activity of new palladium (II) complexes with 5-nitrothiophene-2-carboxaldehyde N (4)- substituted thiosemicarbazones. Bioorg Med Chem 2004; 12: 4679-84.
- - Sisson G., Goodwin A., Raudonikiene A., Hughes N.J., Mukhopadhyay A.K., Berg D.E. and Hoffman P.S. Enzymes associated with reductive activation and action of nitazoxanide, nitrofurans and metronidazole in Helicobacter pylori. Antimicrob. Agents Chemother, 46,
- â2123 (2002)
- - Hoffman J.S. and Caves D.R., Treatment of Helicobacter pylori. Curr. Opin. Gastroenterol, 17, 30â34 (2001)
- - World Health Organization, WHO model list of essential medicines, 15th
- edition, Available: http://www. who.int/medicines/ publications/EssMedList15.pdf. (2013)
- - Kim DW, Park JM, Yoon BW, Baek MJ, Kim JE, Kim SY. Metronidazole-induced encephalopathy. J Neurol Sci 2004; 224: 107-11
- - Upcroft JA, Campbell RW, Benakli K, Upcroft P, Vanelle P. Efficacy of New 5-Nitroimidazoles against Metronidazole-Susceptible and -Resistant Giardia, Trichomonas, and Entamoeba spp. Antimicrobial Agents and Chemotherapy 1999; 43: 73â76.
- -Beena, Kumar Nitin, Rohilla Rajesh K., N. Roy, Rawat Diwan S. . Synthesis and antibacterial activity evaluation of metronidazoleâtriazole conjugates, Bioorg. Med. chem.
- Lett., 19, 1396â1398 (2009)
- - Massimo Bertinaria, Ubaldina Galli,Maria Immacolata Brenciaglia,Giovanni Sorba,Roberta Fruttero,Maria Maddalena Scaltrito, Alberto Gasco, Francesco Dubini. Synthesis and Anti-Helicobacter pylori Properties of NO-Donor/Metronidazole Hybrids and Related compounds,
- Drug Dev. Res, 60, 225â239 (2003)
- - Seref Demirayak, Ahmet Ãagri Karaburun, Nuri Kiraz. 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)
- - Lalit Kumar, Amit Sarswat, Nand Lal, Vishnu L. Sharma, Ashish Jain, Rajeev Kumar, Vikas Verma, Jagdamba P. Maikhuri, Awanit Kumar, Praveen K. Shukla, Gopal Gupta. Imidazole derivatives as possible microbicides with dual protection, Eur. J. Med. Chem., 45, 817â824 (2010)
- - Haythem A. Saadeh, Ibrahim M. Mosleh, Mustafa M. El-Abadelah. New Synthesis and Antiparasitic Activity of Model 5-Aryl-1methyl-4-nitroimidazoles, Molecules, 14, 2758-2767 (2009)
- - Khabnadideh S., Rezaei Z., Khalafi Nezhad, Motazedian M.H., Eskandari M. Synthesis of metronidazole derivatives as antigiardiasis agents, DARU Vol. 15, No. 1 2007
- - Zahra Rezaei, Soghra Khabnadideh, Kamiar Zomorodian, Kyvan Pakshir, Giti Kashi, Narges Sanagoei and Sanaz Gholami. Design, Synthesis and Antifungal Activity of Some New Imidazole and Triazole Derivatives, Arch.Pharm.Chem. Life Sci. 2011, 344 (10), 658-665
- - S. Khabnadideh, Z. Rezaei, Y. Ghasemi, N. Montazeri-Najafabadi. Antibacterial Activity of Some New Azole Compounds, Antiinfective Agents, 2012, 10, 26-33
- - Zahra Rezaei, Soghra Khabnadideh, Keyvan Pakshir, Zahra Hossaini, Fatemeh Amiri, Elham Assadpour, Design, synthesis, and antifungal activity of triazole and benzotriazole derivatives, European Journal of Medicinal Chemistry 44 (2009) 3064â3067