Ether and coumarin–functionalized (benz)imidazolium salts and their silver(I)–N–heterocyclic carbene complexes: Synthesis, characterization, crystal structures and antimicrobial studies

Achar, Gautam; Agarwal, Purvika; Brinda, K.N.; Małecki, Jan Grzegorz; Keri, Rangappa S.; Budagumpi, Srinivasa

doi:10.1016/j.jorganchem.2017.11.005

Cited by 30 publications

(21 citation statements)

References 50 publications

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“…All the synthesized benzimidazolium salts (4a-4j) and their corresponding Ag(I) complexes (5a-5j) were investigated for antibacterial against the gram (+)/(−) bacteria. The DMSO did not exhibit any antimicrobial activity as reported earlier [61][62][63][64][65][66][67][68][69][70][71][72][73].…”

Section: Biological Cytotoxic and Antibacterial Activitiessupporting

confidence: 62%

Novel N-Heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, Antimicrobial, Antioxidant and Cytotoxicity Potential Studies

Slimani¹,

Dridi²,

Özdemır³

et al. 2022

Carbene

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Nowadays, N-heterocyclic carbene-based silver-complexes Ag(I) have been widely used as an organometallic drug candidate in medicinal and pharmaceutical chemistry researches due to their low toxicity. Due to the success of Ag(I) complexes in biological applications, interest in the synthesis and applications of such compounds is increasing rapidly. Therefore, in this study, a series of unsymmetrical N,N-disubstituted benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) (2a-2j). The interaction of these benzimidazolium salts having their two nitrogen atoms substituted by bulky groups with Ag2O in DMF has been carried out to afford Ag(I) complexes and characterized by 1H NMR, 13C NMR, FT-IR and elemental analyses. The antimicrobial activity of Ag(I) complexes was tested against some standard culture collections of Gram-negative, Gram-positive bacterial strains and Fungal strains, which are the most frequently isolated among the society and hospital-acquired infectious microorganisms as potential metallopharmaceutical agents. The Ag-NHC complexes showed effective antimicrobial activity against microorganisms with MIC values between 0.0024 and 1.25 mg/ml. Moreover, these Ag-NHC complexes exhibited significant antioxidant activities. In addition, of benzimidazoles salts 2,4 and Ag(I) complexes 3,5 were screened for their antitumor activity. The highest antitumor activity was observed for 3e and 3d Complexes.

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Section: Biological Cytotoxic and Antibacterial Activitiessupporting

confidence: 62%

Novel N-Heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, Antimicrobial, Antioxidant and Cytotoxicity Potential Studies

Slimani¹,

Dridi²,

Özdemır³

et al. 2022

Carbene

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“…As expected, the C2-proton (NCHN) resonance of the imidazolium salt was notably absent in the 1 H NMR spectrum of 2. 29 This observation conrmed the successful formation of the desired silver complex through the deprotonation of the azolium salt. In the 1 H NMR spectrum, the aromatic protons appeared in the region of 8.19-7.64 ppm, and the singlet at 9.32 ppm belonged to the acridine proton.…”

Section: Resultsmentioning

confidence: 94%

Blue-emitting acridine-tagged silver(i)-bis-N-heterocyclic carbene

et al. 2019

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“…We had shown that those complexes have structures such as [(NHC) 2 Ag + ]AgX 2 − type in solution using LC–MS spectra. After that previous study, Budagumpi and co‐workers reported the crystal structures of coumarin‐tethered Ag(I)–NHC complexes and they showed that these complexes have structures as shown in Scheme in the solid state …”

Section: Resultsmentioning

confidence: 98%

Inhibition of paraoxonase 1 by coumarin‐substituted N‐heterocyclic carbene silver(I), ruthenium(II) and palladium(II) complexes

Karataş

Çalgın

Alıcı

et al. 2019

Applied Organom Chemis

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We synthesized three coumarin‐substituted benzimidazolium chlorides and their silver(I), ruthenium(II) and palladium(II) N‐heterocyclic carbene (NHC) complexes. All compounds were characterized using appropriate spectroscopic techniques and elemental analyses. Single‐crystal X‐ray structure of a Pd(II)–NHC complex (6b) was also determined. The inhibitory properties of all compounds were tested on the activity of human paraoxonase 1 (PON1). All complexes exhibited weaker inhibitory properties than their corresponding benzimidazolium salts except for complex 6b which is the most active inhibitor with an IC50 value of 3.01 μM among the compounds reported in this study. A kinetic evaluation showed that this complex inhibits PON1 activity in a non‐competitive manner. Molecular docking studies were also performed for 6b in order to obtain more insight into the binding mode.

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Ether and coumarin–functionalized (benz)imidazolium salts and their silver(I)–N–heterocyclic carbene complexes: Synthesis, characterization, crystal structures and antimicrobial studies

Cited by 30 publications

References 50 publications

Novel N-Heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, Antimicrobial, Antioxidant and Cytotoxicity Potential Studies

Novel N-Heterocyclic Carbene Silver (I) Complexes: Synthesis, Structural Characterization, Antimicrobial, Antioxidant and Cytotoxicity Potential Studies

Blue-emitting acridine-tagged silver(i)-bis-N-heterocyclic carbene

Inhibition of paraoxonase 1 by coumarin‐substituted N‐heterocyclic carbene silver(I), ruthenium(II) and palladium(II) complexes

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