126401-68-1Relevant articles and documents
Benzimidazole-based silver(I)-N-heterocyclic carbene complexes as anti-bacterials: Synthesis, crystal structures and nucleic acids interaction studies
Asekunowo, Patrick O.,Haque, Rosenani A.,Razali, Mohd. R.,Budagumpi, Srinivasa
, p. 126 - 137 (2015)
A series of new benzimidazolium salts as N-heterocyclic carbene (NHC) precursors has been synthesized. Reactions of these salts with Ag2O with varying metal-to-salt ratio facilitate the formation of a series of new binuclear and mononuclear Ag(I)-NHC complexes. All compounds were characterized using physicochemical and spectroscopic techniques. Single-crystal X-ray diffraction study reveals a binuclear structure for one of the complexes and a mononuclear one for two others. These complexes exist as cationic Ag(I)-NHC complexes with the chelation of carbene carbons to the silver centre in an almost linear manner. The compounds were screened for their anti-bacterial activities against Staphylococcus aureus (ATCC 12600) as a Gram-positive bacterium and Escherichia coli (ATCC 25922) as a Gram-negative bacterium. The results show that both bacteria appear markedly inhibited. Furthermore, the results suggest the possibility of steric variation as a modulation of the anti-bacterial activities. The nuclease activities of the compounds were assessed using gel electrophoresis and the results indicate that these complexes can cleave or degrade DNA and RNA via a non-oxidative mechanism.
Nitrile functionalized silver(I) N-heterocyclic carbene complexes: DFT calculations and antitumor studies
Hussaini, Sunusi Y.,Haque, Rosenani A.,Fatima, Tabinda,Agha, Taleb M.,Abdul Majid,Abdallah, Hassan H.,Razali, Mohd. R.
, p. 301 - 312 (2018)
A series of aliphatic nitrile functionalized benzimidazolium salts and their respective mononuclear N-heterocyclic carbene Ag(I)-NHC complexes are reported. The benzimidazolium salts were synthesized by N-alkylation of 1H-benzimidazole with an appropriate alkyl bromide, followed by reaction with either 5-bromovaleronitrile or 6-bromohexanenitrile. The respective mononuclear Ag(I)-NHC complexes were prepared by the reaction of the benzimidazolium salts with Ag2O. All the synthesized compounds were characterized by physico-chemical and spectroscopic techniques. The molecular structures of the two complexes were elucidated through single-crystal X-ray diffraction analyses. Density functional theory was used to model the structures of the other complexes. The benzimidazolium salts and their complexes were screened for cytotoxicity against a breast cancer cell line (MCF-7), using the MTT assay. All the Ag(I)-NHC complexes gave IC50 values ranging from 7.0?±?1.06 to 12.9?±?1.55?μM which are comparable to the standard drug, tamoxifen (IC50?=?11.2?±?1.84?μM), while all of the benzimidazolium salts proved to be inactive.
Properties of alkylbenzimidazoles for CO2 and SO2 capture and comparisons to ionic liquids
Shannon, Matthew S.,Hindman, Michelle S.,Danielsen, Scott P.O.,Tedstone, Jason M.,Gilmore, Ricky D.,Bara, Jason E.
, p. 1638 - 1647 (2012)
To date, few reports have been concerned with the physical properties of the liquid phases of imidazoles and benzimidazolespotential starting materials for a great number of ionic liquids. Prior research has indicated that alkylimidazole solvents exhibit different, and potentially advantageous physical properties, when compared to corresponding imidazolium-based ionic liquids. Given that even the most fundamental physical properties of alkylimidazole solvents have only recently been reported, there is still a lack of data for other relevant imidazole derivatives, including benzimidazoles. In this work, we have synthesized a series of eight 1-n-alkylbenzimidazoles, with chain lengths ranging from ethyl to dodecyl, all of which exist as neat liquids at ambient temperature. Their densities and viscosities have been determined as functions of both temperature and molecular weight. Alkylbenzimidazoles have been found to exhibit viscosities that are more similar to imidazolium-based ILs than alkylimidazoles, owed to a large contribution to viscosity from the presence of a fused ring system. Solubilities of CO2 and SO2, two species of concern in the emission of coal-fired power generation, were determined for selected alkylbenzimidazoles to understand what effects a fused ring system might have on gas solubility. For both gases, alkylbenzimidazoles were determined to experience physical, non-chemically reactive, interactions. The solubility of CO2 in alkylbenzimidazoles is 10%-30% less than observed for corresponding ILs and alkylimidazoles. 1-butylbenzimidazole was found to readily absorb at least 0.333 gram SO2 per gram at low pressure and ambient temperature, which could be readily desorbed under an N2 flush, a behavior more similar to imidazolium-based ILs than alkylimidazoles. Thus, we find that as solvents for gas separations, benzimidazoles share characteristics with both ILs and alkylimidazoles. Science China Press and Springer-Verlag Berlin Heidelberg 2012.
Synthesis and characterization of ortho-xylyl linked bis-benzimidazolium salts (Part-II)
Haque, Rosenani A.,Iqbal, Muhammad Adnan
, p. 3049 - 3054 (2013)
A number of N-alkylbenzimidazoles were synthesized by reactions of benzimidazole with alkyl halides (PentBr, HexBr, OctBr, DecBr). The subsequent treatment of the resulting N-alkylbenzimidazoles with 1,2-bis(bromomethylene) benzene afforded corresponding bisbenzimidazolium salts. All the compounds were characterized by spectroscopic techniques (NMR and FT-IR) and microanalysis. Molecular structures of selected compounds were established through single crystal X-ray diffraction studies.
A new type of triptycene-based stationary phases with alkylated benzimidazolium cations for gas chromatographic separations
He, Jun,Qi, Meiling
, p. 1415 - 1418 (2019)
Favorable physicochemical properties and unique molecular recognition capability endow triptycene-based materials with good potential as stationary phases for gas chromatography (GC). This work reports a new type of triptycene-based materials functionalized by three benzimidazolium cations with different peripheral alkyl lengths (denoted as TP-3Bim-5C and TP-3Bim-12C) and their GC separation performance. As a result, they shared high resolving performance for the naphthalene isomers but differed for the benzene derivatives with varying polarity. Moreover, their capillary columns exhibited good repeatability and thermal stability. This work presents a facile strategy for tailoring the selectivity of the TP-based stationary phases and demonstrates their promising future for chromatographic analysis.
