Synthesis, crystal structure, structural characterization and in vitro antimicrobial activities of 1-methyl-4-nitro-1H-imidazole

Shahid, Hafiz Abdullah; Jahangir, Sajid; Yousuf, Sammer; Hanif, Muddasir; Sherwani, Sikandar Khan

doi:10.1016/j.arabjc.2014.11.001

Cited by 14 publications

(5 citation statements)

References 25 publications

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“…26 1-Methyl-4-nitro-1H-imidazole is a heterocyclic compound known as antibacterial agent for a long time due to its broad spectrum against gram positive and gram negative bacteria and other organisms, experiments asserted the capability of this substance to inhibit or damage Micrococcus luteus, Staphylococcus aureus and Pseudomonas aeruginosa by producing many different kinds of free radicals, the advantage which isn't observed in derivatives 8-10. 27 The only inhibitory effects observed in this research were related to thiazole derivative 4 and no inhibitory effect was seen for analogues 1-3. It can be due to difference in the structure of derivatives.…”

Section: Resultsmentioning

confidence: 64%

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

Ghasemi¹,

Beyzaei²,

Majidiani³

2016

Pharm Sci

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Section: Resultsmentioning

confidence: 64%

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

Ghasemi¹,

Beyzaei²,

Majidiani³

2016

Pharm Sci

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“…The X-ray crystallographic data for 4-NI indicated a chain of 4-NI molecules built by N (1) -H?N (3) bonding [7,11] between different 4-NI molecules stacked in the same plane. The intermolecular N (1) -H (1) ?N (3) hydrogen bond distance was 2.1 Å [11] at room temperature but decreased to 1.9 Å at 100 K. [7] Moreover, hydrogen bonding is stronger for N (1) -H (1) ?N (3) in the crystal phase, with a H?N length of 1.9 Å compared with the intermolecular hydrogen bond lengths for C ( Interestingly, the more recent crystal structure for CH 3 -4NI [45] shows that molecules do not stack in the same plane and the intermolecular hydrogen bonds are very different. Rather than N (1) -H?N (3) as in 4-NI ( Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Illustration of the intermolecular hydrogen bonding (HB) in crystalline form of (a) 4-NI [11] and (b) CH 3 -4NI. [45] ,13 %, suggesting that the nitrogen atoms of 4-NI and CH 3 -4NI may be subject to multiple configurations, hydrogen bonding, and resonant structures, that are phase dependent. In addition, theoretical considerations need further investigation, e.g.…”

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confidence: 99%

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory

et al. 2021

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Nitroimidazoles and derivatives are a class of active pharmaceutical ingredients (APIs) first introduced sixty years ago. As anti-infection agents, the structure-activity relationships of nitroimidazole compounds have been particularly difficult to study due to their low reduction potentials and unique electronic structures. In this study, we combine dynamic nuclear polarization (DNP)-enhanced solid-state (100 K), solid-state (298 K), and 1 H-13 C heteronuclear single quantum coherence (HSQC) solution-state NMR techniques (303 K) with density functional theory (DFT) to study the 1 H, 13 C, and 15 N chemical shifts of 4-nitroimidazole (4-NI) and 1-methyl-4-nitroimidazole (CH 3-4NI). The 4-NI chemical shifts were observed at 119.4, 136.4, and 144.7 ppm for 13 C, and at 181.5, 237.4, and 363.0 ppm for 15 N. The measurements revealed that methylation (deprotonation) of the amino nitrogen N (1) of 4-NI had less effect (Dd ¼ À4.8 ppm) on the N (1) chemical shift but was compensated by shielding of the N (3) (Dd ¼ 11.6 ppm) in CH 3-4NI. The calculated chemical shifts using DFT for 4-NI and CH 3-4NI agreed well with the experimental values (within 2 %) for the imidazole carbons. However, larger discrepancies (up to 13 %) were observed between the calculated and measured 15 N NMR chemical shifts for the imidazole nitrogen atoms of both molecules, which indicate that effects such as imidazole ring resonant structures and molecular dynamics may also contribute to the nitrogen chemical environment.

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“…68 Nitroimidazole derivatives can also stop bacteria via free radical generation. 69 Tetrahydropyrimidine derivatives 6d and 6f inhibit strains of A. baumannii. It is proposed that tetrahydropyrimidines act as channel blockers or inhibitors of cell surface receptors in the face with bacteria.…”

Section: Discussionmentioning

confidence: 99%

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

et al. 2020

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Background: Acinetobacter baumannii is a common infectious agent in hospitals. New antimicrobial agents are identified and prepared to combat these bacterial pathogens. In this context, the blocking potentials of a series of synthesized N-heterocyclic compounds, Cu/Fe3O4@SiO2 nanocomposites, glycine, poly-L-lysine, nisin and hydroalcoholic extracts of Trachyspermum ammi, Curcuma longa and green tea catechins were evaluated against non-resistant and multidrug-resistant strains of A. baumannii. Methods: Solutions of heterocyclic derivatives and hydroalcoholic extracts of Trachyspermum ammi, Curcuma longa and green tea catechins were prepared at initial concentration of 10240 μg ml-1 in 10% DMSO. Other compounds were dissolved in water at the same concentrations. Their in vitro inhibitory activity was assessed by determination of IZD, MIC and MBC values. Results: Glycine, poly-L-lysine, nisin, Curcuma longa and green tea catechins extracts, and thiazoles 3a, 3d and 3f were ineffective at their initial concentrations. Heterocyclic derivatives 7a-f, 3c, 3e and 3h, Cu/Fe3O4@SiO2 nanocomposites and Trachyspermum ammi extract could block the growth of bacterial strains with IZDs (7.40-15.51 mm), MICs (32-1024 µg ml-1) and MBCs (128-2048 µg ml-1). Conclusion: Among synthetic chemicals and natural products, the best antimicrobial effects were recorded with (E)-2-(5-acetyl-4-methylthiazol-2-yl)-2-(thiazolidin-2-ylidene)acetonitrile (7b) and the extract of Trachyspermum ammi. It is imperative that their toxic and histopathologic effects were assessed in future researches. It is predicted that the essential oil of Trachyspermum ammi will improve its antibacterial activities.

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Synthesis, crystal structure, structural characterization and in vitro antimicrobial activities of 1-methyl-4-nitro-1H-imidazole

Cited by 14 publications

References 25 publications

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

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Synthesis, crystal structure, structural characterization and in vitro antimicrobial activities of 1-methyl-4-nitro-1H-imidazole

Cited by 14 publications

References 25 publications

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

A Comparative Study on the Antibacterial Effects of Some Newly Synthesized Thiazole, Imidazolidine and Tetrahydropyrimidine Derivatives Against Bacillus cereus and Salmonella typhimurium

NMR Chemical Shift and Methylation of 4-Nitroimidazole: Experiment and Theory

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe3O4@SiO2 Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

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Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii