Synthesis, Characterization and Antimicrobial properties of Methylbenzyl and Nitrobenzyl containing Imidazolium-based Silver N -Heterocyclic Carbenes

New weapons are constantly needed in the fight against cancer. The discovery of cisplatin as an anticancer drug prompted the search for new metal complexes. The successful history of cisplatin motivated chemists to develop a plethora of metal‐based molecules. Among them, metal‐N‐heterocyclic carbene (NHC) complexes have gained significant attention because of their suitable qualities for efficient drug design. The enhanced applications of coinage metal‐NHC complexes have encouraged a gradually increasing number of studies in the fields of medicinal chemistry that benefit from the fascinating chemical properties of these complexes. This review aims to present recent developments in synthetic strategies and medicinal applications of copper, silver and gold complexes supported by NHC ligands.

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“…The complexes were purified using hexane and diethyl ether (DEE) and obtained in a good yield of 65–75 % (Scheme 28). [67] …”

Section: Synthetic Strategiesmentioning

confidence: 99%

“…The complexes were purified using hexane and diethyl ether (DEE) and obtained in a good yield of 65-75 % (Scheme 28). [67] Shahini et al 2 equivalent of silver(I) oxide at room temperature in acetonitrile for 4 hours. The bis-NHC complexes were obtained in a good yield in the range of 70-75 % (Scheme 29).…”

Section: Silverà Nhc Complexesmentioning

confidence: 99%

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Nayak

Gaonkar

2021

ChemMedChem

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“…Noteworthy is difference in the reactivity of bromide heteroleptic NHC-Ag(I) complexes depending on the position of the CN group in the N-benzyl substituent in carbene which was found in [95]. In detail, the NHC-Ag(I) complex 41 containing the 4-cyanobenzyl N-substituent in the carbene structure has been involved in the transmetalation reaction with (SMe 2 )Au I Cl in However, it is known that such conditions favor the formation of the homoleptic bis-NHC-Ag(I) complexes [97]. Hence, the effect of the 2-cyanobenzyl substituent on the stabilization of the homoleptic form of complex 42 due to the closeness of the coordinating CN group to the metal center has been suggested.…”

Section: Carbene Transfer Accompanied By the Change In The Metals Oxidation Statementioning

confidence: 99%

Alternative Transformations of N-Heterocyclic Carbene Complexes of the Group 11 Metals in Transmetalation Reactions (A Review)

Mikhaylov

Балова

2021

Russ J Gen Chem

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The carbene transfer from N-heterocyclic carbene complexes of Group 11 metals (NHC-M C ) (especially silver and copper) to other metals is considered a convenient and universal, sometimes having no alternative, method for the synthesis of a wide range of important N-heterocyclic carbene complexes of transition metals. As the number of successful examples of transmetalation with the formation of the target product has increased, the data were accumulated on alternative or unexpected results of the interaction of NHC-M C complexes with compounds of other metals. This review considers the examples of NHC-M C reactions with compounds of other metals which proceed with a change in the metals oxidation state, conversion of (NHC)M C X into cationic homoleptic [(NHC) 2 M C ] + forms, transmetalation retaining the other metal in the coordination sphere of the product, or formation of heterometallic adducts preserving the M C -C carbene bond, rather than these occurring according to the standard reaction pathway. Unusual "reverse" carbene transfer reactions have been considered separately. The review material reveals a promising new synthetic potential of NHC-M C in the reactions with other metals and discusses the possible mechanisms and driving forces of such transformations. The most important aspects of the application of the obtained products, primarily in various catalytic processes, have been considered as well.

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“…These properties can be modified based on the N-substituents. 5 This is because the NHC precursors (in the form of imidazolium salts) were found to be stable to air and moisture. The NHC-carbenes have been applied in the field of medicine as therapeutic agents depending upon their biological activity, which includes but is not limited to, antimicrobial, antiviral, antifungal, and anticancer.…”

Section: Introductionmentioning

confidence: 99%

“…NHC’s extraordinary and unique characteristics, such as being strong σ-electron donors that make them effective ligands, have influenced the study of coordination and organometallic chemistry. These properties can be modified based on the N -substituents . This is because the NHC precursors (in the form of imidazolium salts) were found to be stable to air and moisture.…”

Section: Introductionmentioning

confidence: 99%

Surface-Enhanced Raman Scattering (SERS) in Combination with PCA and PLS-DA for the Evaluation of Antibacterial Activity of 1-Isopentyl-3-pentyl-1H-imidazole-3-ium Bromide against Bacillus subtilis

Tahir,

Kamran,

Majeed

et al. 2024

ACS Omega

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In the current study, surface-enhanced Raman scattering (SERS) was performed to evaluate the antibacterial activity of lab-synthesized drug (1-isopentyl-3-pentyl-1H-imidazole-3-ium bromide salt) and commercial drug tinidazole againstBacillus subtilis. The changes in SERS spectral features were studied for unexposed bacillus and exposed one with various dosages of drug synthesized in the lab (1-isopentyl-3-pentyl-1H-imidazole-3-ium bromide salt), and SERS bands were assigned associated with the drug-induced biochemical alterations in bacteria. Multivariate data analysis tools including principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA) have been utilized to analyze the antibacterial activity of the imidazole derivative (lab drug). PCA was employed in differentiating all the SERS spectral data sets associated with the various doses of the labsynthesized drug. There is clear discrimination among the spectral data sets of a bacterial strain treated with different concentrations of the drug, which are analyzed by PLS-DA with 86% area under the curve in receiver operating curve (ROC), 99% sensitivity, 100% accuracy, and 98% specificity. Various dominant spectral features are observed with a gradual increase in the different concentrations of the applied drug including 715, 850, 1002, 1132, 1237, 1396, 1416, and 1453 cm −1 , which indicate the possible biochemical changes caused in bacteria during the antibacterial activity of the lab-synthesized drug. Overall, the findings show that imidazole and imidazolium compounds generated from tinidazole with various alkyl lengths in the amide substitution can be effective antibacterial agents with low cytotoxicity in humans, and these results indicate the efficiency of SERS in pharmaceuticals and biomedical applications.

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Synthesis, Characterization and Antimicrobial properties of Methylbenzyl and Nitrobenzyl containing Imidazolium-based Silver N -Heterocyclic Carbenes

Cited by 11 publications

References 29 publications

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Alternative Transformations of N-Heterocyclic Carbene Complexes of the Group 11 Metals in Transmetalation Reactions (A Review)

Surface-Enhanced Raman Scattering (SERS) in Combination with PCA and PLS-DA for the Evaluation of Antibacterial Activity of 1-Isopentyl-3-pentyl-1H-imidazole-3-ium Bromide against Bacillus subtilis

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