1137-67-3Relevant articles and documents
Syntheses, structures, and properties of transition metal complexes with 2-(n-pyridyl)benzimidazole (n=2, 3, and 4)
Zhou, Ying-Xia,Li, Xia,Zhaang, Hai-Yan,Fan, Cai-Ling,Zhang, Hong-Yun,Wu, Ben-Lai
, p. 4066 - 4078 (2011)
Three pyridylbenzimidazoles (2-PBIM, 3-PBIM, and 4-PBIM) have been prepared (2-PBIM: 2-(2-pyridyl)-benzimidazole, 3-PBIM: 2-(3-pyridyl)-benzimidazole, 4-PBIM: 2-(4-pyridyl)-benzimidazole). Reactions of several transition metals (Cd2+, Cu2+, Fe2+) with the three ligands gave four new coordination complexes, [(Cd)2(2-PBIM)2(CH 3COO)4] (1), [Cu(3-PBIM)2 (CH 3COO)2] · 2H2O (2), [Cu(4-PBIM) 2(CH3COO)2(H2O)] · H 2O (3), and [Fe(4-PBIM)2 (Cl)2(H 2O)2] (4), respectively. These four complexes have been characterized by X-ray crystallography, IR spectroscopy, and UV absorption spectroscopy. Thermogravimetric properties of 2 and 4 were also measured. X-ray crystallographic studies reveal that these four complexes are very different, although the ligands are similar in structure. The role of hydrogen-bonding and π-π interactions in extending dimensionality of simple complexes has been discussed.
Design, synthesis, binding and docking-based 3D-QSAR studies of 2-pyridylbenzimidazoles - A new family of high affinity CB1 cannabinoid ligands
Mella-Raipan, Jaime A.,Lagos, Carlos F.,Recabarren-Gajardo, Gonzalo,Espinosa-Bustos, Christian,Romero-Parra, Javier,Pessoa-Mahana, Hernan,Iturriaga-Vasquez, Patricio,Pessoa-Mahana, Carlos David
, p. 3972 - 4001 (2013)
A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with Ki values in the nanomolar range. JM-39 (compound 39) was the most active of the series (KiCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q2 = 0.710, r2 = 0.998, r2pred = 0.823).
Structural and luminescent properties of a series of Cd(II) pyridyl benzimidazole complexes that exhibit extended three-dimensional hydrogen bonded networks
Wang, Jin-Hua,Tang, Gui-Mei,Qin, Ting-Xiao,Wang, Yong-Tao,Cui, Yue-Zhi,Ng, Seik?Weng
, p. 1168 - 1189 (2017)
Five new coordination complexes, [CdI2(3-PyBim)](H2O)3 (1), [Cd(SO4)(3-PyBim)(H2O)4] (2), [CdCl2(4-PyBim)2(H2O)2] (3), [CdBr2(4-PyBim)2(H2O)2] (4) and [CdI2(4-PyBim)2(H2O)2] (5) [3-PyBim=2-Pyridin-3-yl-1H-benzoimidazole, 4-PyBim=2-Pyridin-4-yl-1H-benzoimidazole], were obtained under hydrothermal conditions and characterized by single crystal X-ray diffraction, IR, elemental analysis, and powder X-ray diffraction. All of the complexes have mononuclear structures. Among the crystal structures of these complexes, there exist a variety of intermolecular hydrogen bonding interactions and π?π interactions, which further extend to a 3-D supramolecular architecture. The solid state photoluminescent properties of 1–5 vary with the electronegativity of the coordination anion. Additionally, the thermogravimetric analyses of these complexes are discussed.
Two new silver(I) ammine complexes by displacement reaction between [Ag(NH3)2]+ ions and different pyridine-4,5-Imidazoledicarboxylic Acids
Zhou, Rui-Sha,Song, Jiang-Feng,Li, Yan-Bin,Xu, Chun-Yan,Yang, Xiao-Feng
, p. 251 - 256 (2011)
[Ag(NH3)2]+ ions are chosen as an initial reaction precursor because of its simple displacement reaction and intrinsic arrangement as well as specific coordination directionality. Two new silver(I) ammine complexes, Ag2(NH3)HL2 (2) and Ag 2(NH3)2HL3 (3), were obtained by a simple substitution reaction between [Ag(NH3)2] + ions and pyridine-4,5-imidazoledicarboxylic acid [H 3L2 = 2-(3′-pyridyl) 4,5-imidazoledicarboxylic acid and H3L3 = 2-(4′-pyridyl) 4,5-imidazoledicarboxylic acid]. Silver dimers are connected into a 2D layer and 1D chain in complexes 2 and 3, respectively. In complex 2 two kinds of displacement reactions (mono-substituting and bis-substituting) occurred between the ammine molecules in [Ag(NH3)2]+ ions and H3L 2, however, only the mono-substituting reaction occurs in complex 3.
Thermal and Spectral Studies of Peroxo Complexes of Molybdenum(VI) and Tungsten(VI) with Benzimidazole Derivatives
Maurya, Mannar R.,Jayaswal, Mathuresh N.
, p. 446 - 447 (1998)
Synthesis, spectral and thermal studies of diperoxo complexes of molybdenum(VI) and tungsten(VI) with 2-(2-pyridyl)-benzimidazole, 2-(3-pyridyl)benzimidazole and 2,6-bis(benzimidazol-2-yl)pyridine are reported.
Design, Microwave-Assisted Synthesis and in Vitro Antibacterial and Antifungal Activity of 2,5-Disubstituted Benzimidazole
Shi, Yanpeng,Jiang, Kai,Zheng, Ran,Fu, Jiaxu,Yan, Liuqing,Gu, Qiang,Zhang, Yumin,Lin, Feng
, (2019)
Seventeen novel 2,5-disubstituted benzimidazole derivatives were designed, synthesized and evaluated for their antibacterial activities. The tested compounds B1–B4 and C2–C6 exhibited not only good antifungal activity but also favorable broad-spectrum antibacterial activity. Also, the lowest MIC of antibacterial and antifungal activity was 2 μg/mL and 4 μg/mL, respectively. It suggested that the structure of compound including the different substituent and its sites directly affected the efficacy of the synthesized compounds.
Syntheses, crystal structures, and luminescent properties of three metal coordination polymers based on adipic acid and 2-(pyridine-3-yl)-(1 H)-benzimidazole
Wang, Cui-Cui,Wang, Jin-Hua,Tang, Gui-Mei,Wang, Yong-Tao,Cui, Yue-Zhi,Ng, Seik Weng
, p. 3918 - 3931 (2015)
Three new metal coordination polymers constructed from adipic acid and 2-(pyridin-3-yl)-(1H)-benzimidazole ligands, [M(ADP)(3PBI)2(H2O)2]·2H2O (M = Ni and Co for 1 and 2, respectively) and [Cd(ADP)(3PBI)(H2O)] (3) [ADP = adipic acid dianion; 3PBI = 2-(pyridin-3-yl)-(1H)-benzimidazole], have been synthesized by hydrothermal reactions and were characterized by X-ray single-crystal diffraction, elemental analyses, IR, powder X-ray diffraction, and thermogravimetry. Complexes 1 and 2 are isostructural. Both form a 1-D linear chain structure, which is further assembled into a 3-D supramolecular framework by ππ stacking and hydrogen bonding interactions. Complex 3 possesses a binuclear unit and displays a 2-D layer which is further extended to a 3-D supramolecular architecture via hydrogen bonding and other weak packing interactions. The luminescent properties of 3 were investigated in the solid state at room temperature.
A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
Kumar, Sonu,Sarmah, Manash P.,Reddy, Yella,Bhatt, Ashish,Kant, Ravi
, p. 96 - 105 (2021/11/23)
Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.
Application of sulfonic acid fabricated cobalt ferrite nanoparticles as effective magnetic nanocatalyst for green and facile synthesis of benzimidazoles
Yadav, Priyanka,Kakati, Praachi,Singh, Preeti,Awasthi, Satish K.
, (2021/02/06)
This work represents the design and synthesis of efficient sulfonated cobalt ferrite solid acid catalyst. The synthesized solid acid green catalyst was characterized using various techniques viz. FT-IR, powder XRD, SEM, TEM and VSM. The obtained catalyst was used to synthesize biologically significant 2-substituted benzimidazole derivatives by condensation between o-phenylenediamine with various aromatic, aliphatic and heterocyclic aldehydes. High yield (up to 98 %), short reaction time (10?25 min), mild reaction condition, wide functional group tolerance, easy work-up procedure and excellent values of green chemistry metrices such as lower E factor (0.126), high RME value (88.83 %), carbon efficiency (100 %) and high atom economy (AE) value (90.65 %), are some salient features of the present catalytic system. Moreover, the catalyst recovery by simply using an external magnet and catalyst reusability up to 7 times without any significant loss in catalytic efficiency are some additional remarkable features of the current protocol.
Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
, p. 6705 - 6716 (2021/12/31)
We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.
