Synthesis and Antibacterial Activities of New Metronidazole and Imidazole Derivatives

Atia, Abdul Jabar Kh.

doi:10.3390/molecules14072431

Cited by 63 publications

(29 citation statements)

References 13 publications

(12 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Imidazole rings are also frequently present in antibacterial [6–8], antifungal [9–13], antiparasitic [14–15], anticancer [16–17] and antiaggregatory [18] preparations.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Borowiecki¹,

Milner-Krawczyk²,

Plenkiewicz³

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryRacemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.

show abstract

“…Imidazole rings are also frequently present in antibacterial [6–8], antifungal [9–13], antiparasitic [14–15], anticancer [16–17] and antiaggregatory [18] preparations.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Borowiecki¹,

Milner-Krawczyk²,

Plenkiewicz³

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Nitroimidazoles are known for their antibacterial and antiparasitic properties. There have been several pharmacomodulation attempts to improve metronidazole activity on parasites such as Giardia intestinalis or Trichomonas vaginalis , and on anaerobic bacteria of the Clostridium and Bacteroïdes species . Previously, we synthesized a 2‐substituted 5‐nitroimidazole by unimolecular radical nucleophilic substitution (S RN 1), RP 57967, which was shown to be fivefold more active than metronidazole against Clostridium perfringens with higher mutagenicity (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

2,4‐Disubstituted 5‐Nitroimidazoles Potent against Clostridium difficile

et al. 2019

View full text Add to dashboard Cite

Metronidazole is one of the first‐line treatments for non‐severe Clostridium difficile infections (CDI). However, resistance limits its use in cases of severe and complicated CDI. Structure–activity relationships previously described for the 5‐nitroimidazole series have shown that functionalization at the 2‐ and 4‐positions can impart better activity against parasites and anaerobic bacteria than metronidazole. Herein we report the synthesis of new 2,4‐disubstituted 5‐nitroimidazole compounds that show potent antibacterial activity against C. difficile. We used a vicarious nucleophilic substitution of hydrogen (VNS) reaction to introduce a phenylmethylsulfone at the 4‐position and a unimolecular radical nucleophilic substitution (SRN1) reaction to introduce an ethylenic function at the 2‐position of the 5‐nitroimidazole scaffold.

show abstract

“…Metronidazole ( 1 ) (MTZ), a drug under the trade name of Flagyl, is considered as an important therapy for the treatment of various bacterial, and protozoal infections over more than 50 years . It is used as a broad spectrum agent against a variety of pathogenic gram‐negative as well as gram‐positive anaerobes .…”

Section: Introductionmentioning

confidence: 99%

New Benzamide Analogues of Metronidazole‐tethered Triazoles as Non‐sugar Based Inhibitors of β‐Glucuronidase

et al. 2019

View full text Add to dashboard Cite

The present study describes the synthesis, and evaluation of β‐glucuronidase inhibitory potential of metronidazole analogues. Twenty‐four metronidazole‐tethered benzamide triazoles (28‐51) were synthesized using copper‐catalyzed Huisgen alkyne‐azide cycloaddition reaction, and characterized by using different spectroscopic techniques. All of them were identified as new compounds. Compounds 28–51 demonstrated weak to excellent in vitro β‐glucuronidase inhibitory activity with no toxicity against 3T3 mouse fibroblast cell lines. Compound 51 (IC50=12.41 ± 0.58 μM) was found to be the most active β‐glucuronidase inhibitor among the series, with an activity ∼4 times higher than the standard inhibitor, D‐saccharic acid‐1,4‐lactone (IC50=45.75 ± 2.16 μM).

show abstract

Synthesis and Antibacterial Activities of New Metronidazole and Imidazole Derivatives

Cited by 63 publications

References 13 publications

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

2,4‐Disubstituted 5‐Nitroimidazoles Potent against Clostridium difficile

New Benzamide Analogues of Metronidazole‐tethered Triazoles as Non‐sugar Based Inhibitors of β‐Glucuronidase

Contact Info

Product

Resources

About