4981-92-4Relevant academic research and scientific papers
Mercury (II), copper (II) and silver (I) complexes with ether or diether functionalized bis-NHC ligands: Synthesis and structural studies
Liu, Qing-Xiang,Yu, Jie,Zhao, Xiao-Jun,Liu, Shu-Weng,Yang, Xiao-Qiong,Li, Kang-Ying,Wang, Xiu-Guang
, p. 4086 - 4096 (2011)
The oligoether-linked dibenzimidazolium (or diimidazolium) salts, bis[2-(3-ethylbenzimidazolium-1-yl)ethyl]ether diiodide (1), bis[2-(3- nbutylbenzimidazolium-1-yl)ethyl]ether diiodide (2), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylbenzimidazolium- 1-yl) diiodide (3), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3- ethylbenzimidazolium-1-yl) di-hexafluorophosphate (4), 1,1′-[1,2- ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylimidazolium-1-yl) diiodide (5), and their five mercury(ii), copper(ii) and silver(i) complexes with ether or diether linkers mercury-{C,C′-bis[2-(3-ethylimidazolin-2-yliden-1-yl) ethyl]ether} tetraiodomercurate (7), copper-{C,C′-bis[2-(3- nbutylimidazolin-2-yliden-1-yl)ethyl]ether} tetraiodomercurate (8), mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylbenzimidazolin-2-yliden-1-yl)} triiodomercurate acetate (9), silver-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-ethylbenzimidazolin-2-yliden-1-yl)} hexafluorophosphate (10) and mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylimidazolin-2-yliden-1-yl)} tetraiodomercurate (11), as well as one anionic complex bis[2-(3-nbutylbenzimidazolium-1-yl)ethyl]ether di-μ-iodo-bis(diiodomercurate) (6) were prepared and characterized. Each of N-heterocyclic carbene metal complexes 7-11 possesses a macrometallocycle, respectively, formed by one metal atom and one bidentate chelate carbene ligand. In the crystal packing of complexes 6-11, 2D supramolecular layers are formed via intermolecular weak interactions, including π-π interactions, hydrogen bonds, C-H...π contacts and weak Hg...I bonds.
Discovery of amide-functionalized benzimidazolium salts as potent α-glucosidase inhibitors
Ahmad, Matloob,Ashfaq, Usman Ali,Khan, Imran Ahmad,Sultan, Sadia,Zaki, Magdi E. A.
, (2021)
α-Glucosidase inhibitors (AGIs) are used as medicines for the treatment of diabetes mellitus. The α-Glucosidase enzyme is present in the small intestine and is responsible for the breakdown of carbohydrates into sugars. The process results in an increase in blood sugar levels. AGIs slow down the digestion of carbohydrates that is helpful in controlling the sugar levels in the blood after meals. Among heterocyclic compounds, benzimidazole moiety is recognized as a potent bioactive scaffold for its wide range of biologically active derivatives. The aim of this study is to explore the α-glucosidase inhibition ability of benzimidazolium salts. In this study, two novel series of benzimidazolium salts, i.e., 1-benzyl-3-{2-(substituted) amino-2-oxoethyl}-1H-benzo[d]imidazol-3-ium bromide 9a–m and 1-benzyl-3-{2-substituted) amino-2-oxoethyl}-2-methyl-1H-benzo[d] imidazol-3-ium bromide 10a–m were screened for their in vitro α-glucosidase inhibitory potential. These compounds were synthesized through a multistep procedure and were characterized by1H-NMR,13C-NMR, and EI-MS techniques. Compound 10d was identified as the potent α-glucosidase inhibitor among the series with an IC50 value of 14 ± 0.013 μM, which is 4-fold higher than the standard drug, acarbose. In addition, compounds 10a, 10e, 10h, 10g, 10k, 10l, and 10m also exhibited pronounced potential for α-glucosidase inhibition with IC50 value ranging from 15 ± 0.037 to 32.27 ± 0.050 μM when compared with the reference drug acarbose (IC50 = 58.8 ± 0.12 μM). A molecular docking study was performed to rationalize the binding interactions of potent inhibitors with the active site of the α-glucosidase enzyme.
Benzoxazole and dioxolane substituted benzimidazole–based N–heterocyclic carbene–silver(I) complexes: Synthesis, structural characterization and in vitro antimicrobial activity
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Müller-Bunz, Helge,Tacke, Matthias,Patil, Siddappa A.
, p. 1 - 13 (2018)
A novel series of 1,3–benzoxazole and 1,3–dioxolane substituted benzimidazole–based N–heterocyclic carbene (NHC) precursors (6a–b and 11a–b) and their corresponding NHC–silver(I) acetate (12a–b and 14a–b) and bis–NHC–silver(I) hexafluorophosphate complexe
Determination of pKa values of some novel benzimidazole salts by using a new approach with 1H NMR spectroscopy
Mumcu, Akin,Küükbay, Hasan
, p. 1024 - 1030 (2015)
Benzimidazoles and their derivatives including imidazole are studied widely because they exist in the structure of natural products and different drugs. pKa values are extremely important for drug discovery and improvement in order to determine pharmacokinetic and pharmacodynamic features such as permeation through biological barriers, interactions with the target area or side effects. Acid-base features (pKa) have great importance not only for physiological characteristics but also for being used as a ligand or changing physico-chemical features by turning benzimidazoles into salts. Within the scope of this study, a variety of new benzimidazole salts were synthesized, and their characterizations were made by NMR spectroscopy, FTIR spectroscopy and element analysis techniques. The pKa values of synthesized benzimidazole salts were determined by inflection point approach using integration values obtained with 1H NMR spectroscopy and Henderson-Hasselbalch analysis. pKa values of some benzimidazole salts were also determined by potentiometric methods in order to compare those of NMR spectroscopy results.
Synthesis, Structure, and Anticancer Activity of Symmetrical and Non-symmetrical Silver(I)-N-Heterocyclic Carbene Complexes
Atif, Muhammad,Bhatti, Haq Nawaz,Haque, Rosenani A.,Iqbal, Muhammad Adnan,Ahamed Khadeer, Mohammad B.,Majid, Amin Malik Shah Abdul
, p. 1171 - 1189 (2020)
Synthesis and anticancer studies of three symmetrically and non-symmetrically substituted silver(I)-N-Heterocyclic carbene complexes of type [(NHC)2-Ag]PF6 (7–9) and their respective (ligands) benzimidazolium salts (4–6) are describe
Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles
An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong
supporting information, p. 748 - 753 (2022/02/02)
We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc
Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of N-Heterocycles via Manganese-Catalyzed Dehydrogenative Cyclization
Li, Yibiao,Liu, Qiang,Shao, Zhihui,Yuan, Shanshan
supporting information, (2022/02/23)
The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N-heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13C-labeled N-heterocycles using 13CH3OH as a readily accessible 13C-isotope reagent.
Azolium mediated N[sbnd]Heterocyclic carbene selenium adducts: Synthesis, cytotoxicity and molecular docking studies
Ashraf, Rizwan,Bhatti, Haq Nawaz,Iqbal, Muhammad Adnan,Khalid, Zohra,Nazari V, Mansoureh,Sarfraz, Ayesha
, (2021/06/03)
Ionic liquids (ILs) are remarkable for biological activities in numerous medical fields. With the aim of enhancing biological potential of azolium based ILs, four new selenium-N-Heterocyclic Carbene (Se-NHC) adducts were synthesized from bis-imidazolium and bis-benzimidazolium molten salts. Synthesized ILs (L1-L4) and Se-NHC adducts (C1[sbnd]C4) were confirmed through elemental analysis, chromatographic and spectroscopic techniques including UHPLC-PDA, FTIR, 1H NMR & 13C NMR spectroscopy as well as mass spectrometry. The compounds were found stable in solution form for upto 96 h measured spectroscopically and showed partition coefficient with optimum lipophilicity measured through shake flask method. The simulation studies of these compounds for cancerous proteins indicated that there could be good to high anticancer potential due to their high affinity and less binding energies for COX-1, EGF, VEGF-A and HIF cancer protein targets. The In Vitro cytotoxicity study of compounds confirmed that these compounds were found highly active showeing IC50 against HCT-116 (1.074–1.116 μg mL?1), A549 (0.977–1.325 μg mL?1) and MCF-7 (0.869–1.378 μg mL?1) which is almost better than standard drug 5-Flourouracil but slightly lower than cisplatin and oxaliplatin. The interaction study of compounds with albumin proteins (BSA) and hemolysis assay assured their least toxicity.
Benzimidazole- And Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities
Banerjee, Kaustav,Bhattacherjee, Debojit,Mahato, Sulendar K.,Sufian, Abu,Bhabak, Krishna Pada
, p. 12984 - 12999 (2021/08/30)
Three new classes of ionic organoselenium compounds containing cationic benzimidazolium and imidazolium ring systems with selenocyanates as counterions are described. The cyclization of N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)2-Br and N-(CH2)3-Br groups in the presence of potassium selenocyanate (KSeCN) led to formation of the corresponding selenazolium selenocyanates (21a, 21b, 22a, and 22b) and selenazinium selenocyanates (21c, 21d, 22c, and 22d). However, the open-chain selenocyanates with additional selenocyanate counterions (21e, 21f, 22e, and 22f) were formed from the N,N′-disubstituted benzimidazolium and imidazolium bromides having N-(CH2)6-Br groups. Mechanistic studies were carried out to understand the feasibility of such cyclization processes in the presence of KSeCN. The compounds were studied further for their potencies to catalytically reduce H2O2 in the presence of thiols. Interestingly, the cyclic selenazolium (21a, 21b, 22a, and 22b) and selenazinium compounds (21c, 21d, 22c, and 22d) exhibited significantly higher antioxidant activities than the corresponding acyclic selenocyanates (21f, 22e, and 22f). Selected compounds (22d and 22e) were further evaluated for their potencies in modulating the intracellular level of reactive oxygen species (ROS) in a representative macrophage cell line (RAW 264.7). Owing to the cationic nature of compounds, they may target and scavenge mitochondrial ROS in the cellular medium.
Naphthalene derivative fluorescent probe as well as preparation method and application thereof
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Paragraph 0036-0040, (2021/06/23)
The invention discloses a naphthalene derivative fluorescent probe as well as a preparation method and application thereof, and relates to a fluorescent detection probe as well as a preparation method and application thereof. In order to solve the technic
