Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides

Al-Mohammed, Nassir N.; Alias, Yatimah; Abdullah, Zanariah; Shakir, Raied Mustafa; Taha, Ekhlass M.; Hamid, Aidil Abdul

doi:10.3390/molecules181011978

Cited by 71 publications

(48 citation statements)

References 41 publications

(45 reference statements)

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“…The minimum inhibitory concentration for complex 5 is small suggesting its high biological efficacy. The reason can be explained based on the Overtone's concept [42] and Tweedy's Chelation theory [43]. The polarity of the metal ion decreases after the chelation owing to the overlap of the planar ligand orbitals which causes increase in the delocalization of p-electrons over the whole chelate ring.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Effective DNA binding and cleaving tendencies of malonic acid coupled transition metal complexes

Pravin¹,

Utthra²,

Kumaravel³

et al. 2016

Journal of Molecular Structure

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Section: Antimicrobial Activitymentioning

confidence: 99%

Effective DNA binding and cleaving tendencies of malonic acid coupled transition metal complexes

Pravin¹,

Utthra²,

Kumaravel³

et al. 2016

Journal of Molecular Structure

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“…18,19 From the ILs' structure point of view, Poly-functionalized heterocyclic compounds containing imidazole and its derivatives are acquiring more importance due to their biological activity. 46 However, many research works dealt with geminal di-cationic ILs synthesis when it comes to their design, 6,7,9,18,[47][48][49][50][51][52] while limited studies have considered dicationic ILs with high rigid spacer. imidazolium, benzimidazolium, pyridinium, pyrrolium, pyrrolidinium and ILs with bridged structures.…”

Section: Introductionmentioning

confidence: 99%

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

2015

Self Cite

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Based on bis-imidazolium and benzimidazolium, new sets of geminal dicationic ionic liquids containing sulphonamide moiety were successfully synthesized with good yields. Their structures were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, and mass spectroscopy. Selected physicochemical properties of these ILs including; thermal stability by TGA and miscibility in some common organic solvents and water were also determined. Most of the prepared dicationic ILs displayed significant level of antibacterial activities against ten selected bacterial strains of Gram-positive and Gram-negative using micro-broth dilution assay. ͞ calcd. for C 29 H 42 N 5 O 6 S 3+ : 588.2856, found: 588.2919; m/z, [NTF 2 ] ͞ calcd. for C 2 F 6 NO 4 S 2 − : 279.9173, found: 279.9145. N,N-bis[(3-allyl-benzimidazol-1-iumyl)ethyl]-4-methylbenzenesulphonamide-bis(trifluorometh- ylsulphonyl)amide (8a)This compound was prepared analogously to 7d using N, N-bis[(3-allyl-benzimidazol-1-iumyl) ethyl]-4-methylbenzenesulphonamide bromide 6a (0.7 g, 1.0 mmole) and Lithium bis-(trifluoromethanesulphonyl)imide LiNTf 2 (0.72 g, 2.5 mmol) to provide a clear viscous hygroscopic liquid at room temperature in 90% yield (1 g). Ten standard strains of Gram positive and negative bacteria were used to evaluate the antibacterial activities of the synthesized ILs compounds; 5a-f and 6a-f. Based on CLSI guidelines 85 , the activities were assessed in terms of minimum inhibitory concentrations (MICs) using microbroth dilution assays. The MIC's values are given in mg/mL and defined as a lowest concentration that inhibits the bacterial strains growth. Gram positive bacteria included: Streptococcus pyogenes ATCC19615, Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC6051, Rodococcus Ruber ATCC27863, Enterococcus faecalis ATCC 29212, Staphylococcus epidermidis ATCC12228, while Gram negative bacteria included: Escherichia coli ATCC10538, Salmonella typhimurium ATCC14028, Pseudomonas aeruginosa ATCC15442, Acinetobacter calcoaceticus ATCC 23055. These standards strains were obtained from the collection Distilled water was used as negative control to dissolve all the tested ILs in concentrations range of 0.05-0.5 mg/mL, while, commercial antibiotics amoxicillin and kanamycin were used as a positive control in the same range of concentrations. A loopful of bacterial cells from the nutrient agar plates ofThe incorporated benzenesulfonamide moiety and the active side substituents into diimidazolium and benzimidazolium cations enhanced both antibacterial activity and miscibility for the synthesized gimini type ILs.

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“…Studies have shown that sulfonamide compounds were used as antibacterial [7][8][9], antifungal [9,10], antiviral [11], anticancer [12], antinflammatory, analgesic [13][14][15], and antibacterial agents [16]. Also, a wide variety of benzimidazole derivatives have been described for their chemotherapeutic importance [17][18][19][20][21][22][23] and oxazole derivatives play very important role in the manufacturing process of various biologically active drugs as anticancer, antimicrobial, antidiabetic and antiobesity [24,25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of some 1,2,4-triazolo[1,5-a]pyridine, pyrimidine sulfonamides and sulfinyl derivatives

Abdel-Motaal

Raslan

2014

Eur. J. Chem.

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Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides

Cited by 71 publications

References 41 publications

Effective DNA binding and cleaving tendencies of malonic acid coupled transition metal complexes

Effective DNA binding and cleaving tendencies of malonic acid coupled transition metal complexes

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

Synthesis and antimicrobial evaluation of some 1,2,4-triazolo[1,5-a]pyridine, pyrimidine sulfonamides and sulfinyl derivatives

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