Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria

Wright, Brian; Shah, Parth; McDonald, Lucas; Shaeffer, Michael L.; Wagers, Patrick O.; Panzner, Matthew J.; Smolen, Justin A.; Tagaev, Jasur A.; Tessier, Claire A.; Cannon, Carolyn L.; Youngs, Wiley J.

doi:10.1039/c2dt00055e

Cited by 41 publications

(24 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Although these systems have shown impressive anticancer activity, their principal drawback remains their limited solubility in water, which severely impairs the ability to administer these compounds systemically. Through the rational selection of substituents of the N -heterocycle, we have strived to synthesize the corresponding salts to have a higher solubility in water, while still maintaining the lipophilicity that is believed to contribute to their efficacy (Wright et al ., 2012; Li et al ., 2010; Youngs et al ., 2012b, c). Additionally, by creating several analogs of an already effective lipophilic imidazolium salt, IC23 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

et al. 2015

Self Cite

View full text Add to dashboard Cite

The anti-tumor activity of imidazolium salts is highly dependent upon the substituents on the nitrogen atoms of the imidazolium cation. We have synthesized and characterized a series of naphthalene-substituted imidazolium salts and tested them against a variety of non-smallcell lung cancer cell lines. Several of these complexes displayed anticancer activity comparable to cisplatin. These compounds induced apoptosis in the NCI-H460 cell line as determined by Annexin V staining, caspase-3, and PARP cleavage. These results strongly suggest that this class of compounds can serve as potent chemotherapeutic agents.

show abstract

Section: Introductionmentioning

confidence: 99%

Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…• C and high yields of isolated product were obtained (Table, entries [14][15][16][17][18][19]. These results indicate that the use of volatile solvents in the three-component coupling reactions could be avoided and thus it can be considered to provide an important contribution to reducing environmental pollution.…”

Section: Catalytic Activity Of the Nhc Silver Complexesmentioning

confidence: 67%

Ag(I) complexes of benzimidazol-2-ylidene ligands: a study of catalytic efficiency towards three-component coupling reactions

Kılınçarslan¹,

Sadıç²,

Çetınkaya³

2016

Turk J Chem

View full text Add to dashboard Cite

Abstract:The N -heterocyclic carbene (NHC)-Ag(I) complexes 3a-c were synthesized from benzimidazolium chlorides (2a-c = NHC.HCl), incorporating benzyl derivatives and a 2-methoxyethyl group (a: 3 N = 2,4,6-trimethylbenzyl; b:3 N = 2,3,5,6-tetramethylbenzyl; c: 3 N = pentamethylbenzyl). The compounds were characterized by spectroscopic and elemental analyses. The synthesized NHC-Ag(I) complexes (3a-c) were tested as catalysts for the catalytic threecomponent coupling reaction of aldehyde, alkyne, and amine to propargylamines in various solvents. All complexes were active catalysts for catalytic three-component coupling reactions with good yields under neat and mild conditions (after 4 h, yields of up to 94%).

show abstract

“…[54] Wright et al [55] synthesized three new silver N-heterocyclic carbine (NHC) complexes that appeared to possess good to excellent activities. Given its superior activity against antibiotic-resistant bacteria, silver carbine complexes (SCCs)h ave been researched.…”

Section: Benzimidazole-metal Complexesmentioning

confidence: 99%

Recent Development of Benzimidazole‐Containing Antibacterial Agents

Song

2016

ChemMedChem

116

View full text Add to dashboard Cite

Clinically significant antibiotic resistance is one of the greatest challenges of the twenty-first century. However, new antibacterial agents are currently being developed at a much slower pace than our growing need for such drugs. Given their diverse biological activities and clinical applications, many bioactive heterocyclic compounds containing a benzimidazole nucleus have been the focus of interest for many researchers. The benzimidazole nucleus is a structural isostere of naturally occurring nucleotides. This advantage allows benzimidazoles to readily interact with the various biopolymers found in living systems. In view of this situation, much attention has been given to the exploration of benzimidazole-based antibacterial agents, leading to the discovery of many new chemical entities with intriguing profiles. In this minireview we summarize novel benzimidazole derivatives active against various bacterial strains. In particular, we outline the relationship between the structures of variously modified benzimidazoles and their antibacterial activity.

show abstract

Synthesis, characterization, and antimicrobial activity of silver carbene complexes derived from 4,5,6,7-tetrachlorobenzimidazole against antibiotic resistant bacteria

Cited by 41 publications

References 34 publications

Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

Ag(I) complexes of benzimidazol-2-ylidene ligands: a study of catalytic efficiency towards three-component coupling reactions

Recent Development of Benzimidazole‐Containing Antibacterial Agents

Contact Info

Product

Resources

About