Synthesis of new metronidazole derivatives with suspected antimicrobial activity (original) (raw)
Related papers
Synthesis and antibacterial activity evaluation of metronidazole–triazole conjugates
Bioorganic & Medicinal Chemistry Letters, 2009
Synthesis and antibacterial activity of metronidazole-triazole conjugates are reported. Total 21 hybrid compounds have been synthesized with different substitution pattern on the triazole ring in order to study their influence on the antibacterial activity. These compounds demonstrated potent to weak antibacterial activity against Gram-positive, and Gram-negative bacteria. Six compounds have shown equal or better antibacterial activity against Gram-negative strains than the reference compound.
ChemInform, 2010
Prc r arati nn or mctronidazo lc derivatives 2-5 is described and the results of antimicrobial evaluation and mutageni city arc givcn. Comrou nd s 2 and 5 at higher concentrati ons show better anti protozoal acti vity than thc parent drug. When tested again~t i'cw strain s of Burteroides f ragilis, an anaerobi c microorganism, compound 2 is found to be active o n four strains, l'lllllrOUIHI 4 to he active agai nst two strai n whereas 3 and 5 are effective against only one strain. In mutagenicity assay 4 is rou nd to hc I cs~ mut agcn ic th an the parent drug.
2-Substituted ethyl]-2-methyl-5-nitroimidazole derivatives, synthesis and antibacterial activities
In this study, seven diverse 1-[2-substituted ethyl]-2-methyl-5-nitroimidazole derivatives were synthesized by reacting various reagents with metronidazole, miscellaneous derivatives were synthesized that represent different scaffolds. The structure elucidation of the compounds was performed by IR, 1 H-NMR, 13 C-NMR and EI-MS. Antimicrobial activities of the compounds were examined and notable activities were observed. Although metronidazole had no activities against aerobic bacteria, synthetic benzene sulfonated metronidazole derivative (M1) exerts some inhibition on Staphylococcus aureus (MIC =250 µg/ml) and phenylacetamide metronidazole derivative (M3) exerts certain effect on Streptoccocus B (MIC = 187.5 µg/ml).
New Derivatives of Benzimidazole and Their Antimicrobial Activity
Journal of Chemotherapy, 1999
Azolium salts and neutral 2-aryl derivatives of benzimidazole, benzothiazole and benzoxazole were synthesized and compounds were identified by 1 H and 13 C NMR spectroscopy and microanalytical methods. In this work the salts 1 and the neutral compounds 2 were evaluated for their in vitro antimicrobial activity against standard strains: Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Candida albicans and Candida tropicals. The compounds 1f, 1g, 1l, lm, 1n, 2a, 2b, 2c, 2e, 2f showed antimicrobial activity against Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Candida albicans and Candida tropicals, with minimum inhibitory concentrations (MICs) ranging between 50 to 200 m mg/mL. Compounds 1f, 1g, 1l, 1m, 2b, 2c showed the highest activity. Benzothiazolium and benzoxazolium salts were more active than 1,3-disubstituted benzimidazolium salts and neutral 2-substituted benzimidazole, benzothiazole and benzoxazole derivatives.
2000
Prc r arati nn or mctronidazo lc derivatives 2-5 is described and the results of antimicrobial evaluation and mutageni city arc givcn. Comrou nd s 2 and 5 at higher concentrati ons show better anti protozoal acti vity than thc parent drug. When tested again~t i'cw strain s of Burteroides f ragilis, an anaerobi c microorganism, compound 2 is found to be active o n four strains, l'lllllrOUIHI 4 to he active agai nst two strai n whereas 3 and 5 are effective against only one strain. In mutagenicity assay 4 is rou nd to hc I cs~ mut agcn ic th an the parent drug.
Synthesis of metronidazole derivatives as antigiardiasis agents
DARU Journal of …, 2007
Metronidazole (MTZ) and its derivatives have been extensively used to treat infections caused by protozoa and anaerobic bacteria. In this investigation several novel imidazole and nitroimidazol derivatives namely: 2-(1H-1-imidazolyl)-1-phenyl-1-ethanol 1a, 2-(2-methyl-1H-1-imidazolyl)-1-phenyl-1-ethanol 1b, 2-(2-methyl-4-nitro-1H-1-imidazolyl)-1-phenyl-1ethanol 1c, 2-(1H-1-imidazolyl)-1-cyclohexanol 2d and 2-(2-methyl-4-nitro-1H-1imidazolyl)-1-cyclohexanol 2e were prepared by the reaction of the corresponding imidazoles with styrene oxide or cyclohexene oxide respectively and their biological activity against Giardia lamblia cyst in compareison with MTZ were determined by flotation technique based on Bingham method. These compounds were less active than metronidazole but showed significant antigiardiasis activity.
Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol
Chemical Biology & Drug Design
Two series of metronidazole derivatives (ester derivatives and ether derivatives) were prepared reacting metronidazole and its acetic acid oxidized form with menthol, thymol, carvacrol, and eugenol. Both series of compounds were tested in vitro against two strains of Helicobacter pylori (the ATCC 26695 and P12), and one strain of Clostridium (Clostridium perfringens). Most of the prepared compounds showed biological activity against the targeted bacteria. Compound 11 was highly active against all tested bacterial strains, especially against P12 with IC 50 0.0011 μM/ml. Compound 6 was highly active against C. perfringens with MIC 0.0094 nM/ml. Viability test was conducted for compound 11 to test its selectivity for normal human fetal lung fibroblasts (MRC5), and it was found to be non-toxic with IC 50 more than 50 μM/ml.
Synthesis and Characterization of Benzimidazole Derivatives for Antimicrobial Property
IJPSM, 2021
Benzimidazoles are an important class of compounds with a wide spectrum of biological activity ranging from anti-hypertensive, anti-viral, anti-microbial, antitumor and anthelmintic activity. Benzimidazole rings are the most important nitrogen-containing heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Due to their special structural features and electron-rich environment, Benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of bioactivities. Numerous benzimidazole based drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potential. The main objective of present work was to study the anti-microbial activity of the Benzimidazole derivatives. A series of benzimidzole derivatives have been synthesized and identified. The compounds were synthesized by using ethyl acetate and benzene as starting material. The series of 1, 2-disubstituted benzimidazoles containing pyrimidine and other functional groups was prepared which provides advantages such as, easy workup and high yield. All reagents used for synthesis were of synthetic grade. Purification of all compounds was done by thin layer chromatography using silica gel G as absorbent on glass plate using acetate: benzene (6:4 v/v %), Toluene: Acetone (8:2 v/v %) and Ethyl Acetate: n-Hexane (6:4 v/v %) as mobile phase. Compounds were detected by using iodine vapor as detecting agent. All compounds show single spot. All the newly synthesized compounds were characterized by IR spectral study. The compounds were investigated for their antimicrobial activity against clinical standard drug Ciprofloxacin. The anti-microbial study of the synthesized derivative was done Broad panels of bacterial and fungal strains were used for testing the antimicrobial properties of the synthesized molecules III1-13. The compounds III 1 (m-NO 2), III 2 (p-NO 2), III 3 (m-Cl), III 4 (3-F-4-Cl) and III 9 (p-OCH 3) showed excellent activity (62.5 μg/ml), even better than ciprofloxacin.