Picolyl and benzyl functionalized biphenyl NHC carbenes and their silver complexes: Sigma donating and antimicrobial properties

Muniyappan, N.; Advaya, Geetha Raghuthaman; Sujitha, Elanseralathan; Sabiah, Shahulhameed

doi:10.1016/j.jorganchem.2021.122075

Cited by 7 publications

(5 citation statements)

References 88 publications

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“…The bond angles of C–Ag–C in 1 – 4 were from 165.8(1) to 178.2(4)°. These values were close to reported values of NHC–silver(I) complexes. ,, …”

Section: Resultssupporting

confidence: 90%

“…In the crystal packing of L 3 H 2 ·(Br) 2 (Figure S1), a two-dimensional network was formed via C–H···Br H-bonds. − In the H-bonds, the hydrogen atoms came from imidazole rings, fluorene, or CH 2 (the data of H-bonds being shown in Table S5). In 1 , two-dimensional layer was formed via C–H···O H-bonds (Figure S2).…”

Section: Resultsmentioning

confidence: 99%

“…Herein, we reported the preparation and structure of six fluorene-bridged bisazolium (azolium = benzimidazolium or imidazolium) salts L 1 H 2 •X 2 -L 6 complexes. 40,46,47 In macrometallocycle 1 (Figure 2), each Ag + was coordinated to two C carbene atoms, and the 28-membered macrometallocycle was constructed through two silver(I) ions and two biscarbene ligands (L 1 ).…”

Section: ■ Introductionmentioning

confidence: 99%

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Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺

et al. 2022

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A series of fluorene-bridged bisazolium salts L 1 H 2 ·X 2 -L 6 H 2 ·X 2 (X = Br– or PF6 –) and six related N-heterocyclic carbene silver(I) complexes [(L1Ag)2](NO3)2 (1), {[L2Ag2(CH3CN)2]2}(PF6)4 (2), [(L3Ag)2(Ag2Br4)] n (3), [(L4Ag) (NO3)] n (4), [L5Ag2Br2] n (5), and [L6(AgCl)2] (6) have been synthesized and characterized. Each cationic moiety of 1 or 2 contained one 28-membered macrometallocycle formed via two silver(I) ions and two biscarbene ligands (L 1 for 1 and L 2 for 2). 1D coordination polymeric chains of 3–5 were formed by different monomers. The open structure of 6 was formed through one biscarbene ligand L 6 and two [AgCl] units, in which two [AgCl] units pointed to opposite directions. Additionally, the recognition performance of 2 to Cu2+ was researched through fluorescence spectra, UV/vis spectra, 1H NMR titrations, HRMS, IR spectra, and the quantum chemical computations. The results showed that 2 can effectually differentiate Cu2+ from other cations.

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“…The bond angles of C–Ag–C in 1 – 4 were from 165.8(1) to 178.2(4)°. These values were close to reported values of NHC–silver(I) complexes. ,, …”

Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺

et al. 2022

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“…Recently, Muniyappan et al synthesized silver complexes bearing picolyl and benzyl linked biphenyl NHC ligands (177-179) [63]. These biphenyl NHC ligands showed the inherent sigma donating properties through proton-coupled carbon NMR spectroscopy.…”

Section: Nhc-silver Complexes With Nitrogenous Substituentsmentioning

confidence: 99%

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

2023

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Silver has a long history of antimicrobial activity and received an increasing interest in last decades owing to the rise in antimicrobial resistance. The major drawback is the limited duration of its antimicrobial activity. The broad-spectrum silver containing antimicrobial agents are well represented by N-heterocyclic carbenes (NHCs) silver complexes. Due to their stability, this class of complexes can release the active Ag+ cations in prolonged time. Moreover, the properties of NHC can be tuned introducing alkyl moieties on N-heterocycle to provide a range of versatile structures with different stability and lipophilicity. This review presents designed Ag complexes and their biological activity against Gram-positive, Gram-negative bacteria and fungal strains. In particular, the structure–activity relationships underlining the major requirements to increase the capability to induce microorganism death are highlighted here. Moreover, some examples of encapsulation of silver–NHC complexes in polymer-based supramolecular aggregates are reported. The targeted delivery of silver complexes to the infected sites will be the most promising goal for the future.

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“…Benzimidazolium salts and their metal complexes have important biological properties, such as antimicrobial and anticancer activity, as well as successful applications in enzyme inhibition. [10][11][12] In addition, these compounds are used as strong and reactive catalysts in arylation, alkylation, transfer hydrogenation, amination, etc. reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological activity of 1,3-disubstitued benzimidazolium salt and its Ag-NHC complex

Ulu

2023

Maced. J. Chem. Chem. Eng.

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In this study, a 1,3-dioxane functionalized benzimidazole salt and its Ag-complex were synthe-sized. The prepared compounds were structurally verified by several spectroscopic techniques including 1H NMR, 13C NMR, FT-IR, LC-MS, and C, H, N analysis. Compounds were evaluated for their in vitro antioxidant activity. The salts and their Ag-NHC complexes were further evaluated for their in vitro anti-cancer activities against HCT-116 human colon cancer cells. The results showed that complex 2 exhibited high activity (4.1 times) against the cancer cell lines studied when compared to the reference drug cispla-tin. Stability studies demonstrated that these compounds are stable in aqueous and organic solutions.

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Picolyl and benzyl functionalized biphenyl NHC carbenes and their silver complexes: Sigma donating and antimicrobial properties

Cited by 7 publications

References 88 publications

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

Synthesis, characterization, and biological activity of 1,3-disubstitued benzimidazolium salt and its Ag-NHC complex

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Picolyl and benzyl functionalized biphenyl NHC carbenes and their silver complexes: Sigma donating and antimicrobial properties

Cited by 7 publications

References 88 publications

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu2+

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu2+

Structure–Activity Relationships in NHC–Silver Complexes as Antimicrobial Agents

Synthesis, characterization, and biological activity of 1,3-disubstitued benzimidazolium salt and its Ag-NHC complex

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Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu²⁺