3878-19-1Relevant articles and documents
Design, synthesis, molecular docking and cytotoxic evaluation of novel 2-furybenzimidazoles as VEGFR-2 inhibitors
Abdullaziz, Mona A.,Abdel-Mohsen, Heba T.,El Kerdawy, Ahmed M.,Ragab, Fatma A.F.,Ali, Mamdouh M.,Abu-bakr, Sherifa M.,Girgis, Adel S.,El Diwani, Hoda I.
, p. 315 - 329 (2017)
Inhibition of angiogenesis through inhibition of vascular endothelial growth factor receptor 2 (VEGFR-2) has been applied in cancer therapy because of its important role in promoting cancer growth and metastasis. In the presented study, a series of benzimidazol-furan hybrids was designed and synthesized through facile synthetic pathways. Evaluation of the synthesized compounds for their in?vitro cytotoxic activity against breast (MCF-7) and hepatocellular (HepG2) carcinoma cell lines was performed. Two of the synthesized conjugates, 10b and 15, showed potent antiproliferative properties against MCF-7 cell line (IC50?=?21.25, 21.35?μM, respectively) in comparison to tamoxifen (IC50?=?21.57?μM). Additionally, compounds 10a, 10b, 15 and 17 showed promising potency (IC50?=?25.95, 22.58, 26.94 and 31.06?μM, respectively) against liver carcinoma cell line HepG2 in contrast to cisplatin (IC50?=?31.16?μM). Moreover, in?vitro evaluation of the synthesized compounds for their effect on the level of VEGFR-2 in MCF-7?cell line showed their potent inhibitory activity relative to control untreated cells. Four compounds 10a, 10b, 14 and 15 showed 92–96% reduction in VEGFR-2 level, compared with tamoxifen and sorafenib which showed inhibition percentage of 98% and 95.75%, respectively. Compound 10a was found to have promising VEGFR-2 inhibitory activity (IC50?=?0.64?μM) in comparison to sorafenib (IC50?=?0.1?μM). Molecular docking was performed to study the binding pattern of the newly synthesized compounds with VEGFR-2 active site. Molecular docking attributed their good VEGFR-2 inhibitory activity to their hydrogen bonding interaction with the key amino acids in VEGFR-2 active site, Glu885 and Asp1046, and their hydrophobic interaction by their 2-furylbenzimidazole moiety with the allosteric hydrophobic back pocket in a type III inhibitors-like binding mode. The binding interaction is augmented by a ring substituent with long chain extension at position 1 of the benzimidazole due to its hydrophobic interaction with the hydrophobic side chains of the amino acids at the interface between the ATP binding site and the allosteric back pocket. Structure-activity relationship (SAR) was inferred for future optimization based on the performed biological and docking studies.
Synthesis and anomeric configuration of 2-(erythrofuranosyl)benzimidazole C-nucleoside analogues
Sallam, Mohammed A. E.,Ibrahim, El-Sayed I.,El-Eter, Khaled A.A.,Cassady, John M.
, p. 93 - 104 (1997)
Anomeric 2-(α- and β-D-erythrofuranosyl)benzimidazole C-nucleoside analogues 2 and 3, were prepared from the corresponding epimeric 2-(D-arabino, and D-ribo-tetritol-1-yl)-benzimidazole analogues 1 and 4, respectively. Similarly, 2-(β-L-erythrofuranosyl)benzimidazole 13 was obtained from the precursor 2-(L-arabino-tetritol-1-yl)benzimidazole 12. The structure and anomeric configuration of the C-nucleoside analogues 2, 3, and 13 were determined by acylation, 1H and 13C NMR spectroscopy, and mass spectrometry.
[Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study
Brahman, Dhiraj,Chhetri, Sailesh,Kamath, Amarjit,McArdle, Patrick,Sinha, Biswajit
, (2021/09/04)
Metal-organic hybrid complexes often exhibit large surface area, pore volume, fascinating structures and potential applications including catalytic applications. Hence a new metal-organic hybrid complex [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)] was synthesized using conventional method. Physico-chemical characterization of the complex was performed with FTIR spectroscopy, single crystal X-ray diffraction, TGA, EPR and FESEM. Single crystal X-ray diffraction study suggests it to be three dimensional with space group P212121 (orthorhombic). The crystal achieves its three-dimensional structure and stability through extensive intermolecular hydrogen bonding. Hirshfeld surface analysis, catalytic activity and DFT study of the complex was also performed. The synthesized complex acts as good catalyst in benzimidazole synthesis with good recyclability as catalyst up to 5th run.
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.
H2 Activation with Co Nanoparticles Encapsulated in N-Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles
Lin, Chuncheng,Wan, Weihao,Wei, Xueting,Chen, Jinzhu
, p. 709 - 720 (2020/11/30)
Co nanoparticles (NPs) encapsulated in N-doped carbon nanotubes (Co@NC900) are systematically investigated as a potential alternative to precious Pt-group catalysts for hydrogenative heterocyclization reactions. Co@NC900 can efficiently catalyze hydrogenative coupling of 2-nitroaniline to benzaldehyde for synthesis of 2-phenyl-1H-benzo[d]imidazole with >99 % yield at ambient temperature in one step. The robust Co@NC900 catalyst can be easily recovered by an external magnetic field after the reaction and readily recycled for at least six times without any evident decrease in activity. Kinetic experiments indicate that Co@NC900-promoted hydrogenation is the rate-determining step with a total apparent activation energy of 41±1 kJ mol?1. Theoretical investigations further reveal that Co@NC900 can activate both H2 and the nitro group of 2-nitroaniline. The observed energy barrier for H2 dissociation is only 2.70 eV in the rate-determining step, owing to the presence of confined Co NPs in Co@NC900. Potential industrial application of the earth-abundant and non-noble transition metal catalysts is also explored for green and efficient synthesis of heterocyclic compounds.
s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles
An, Wan-Kai,Zheng, Shi-Jia,Zhang, Hui-Xing,Shang, Tian-Tian,Wang, He-Rui,Xu, Xiao-Jing,Jin, Qiu,Qin, Yuchen,Ren, Yunlai,Jiang, Song,Xu, Cui-Lian,Hou, Mao-Song,Pan, Zhenliang
supporting information, p. 1292 - 1299 (2021/02/26)
Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featurings-tetrazine units and surface areas larger than 700 m2g?1through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.
Al2O3/CuI/PANI nanocomposite catalyzed green synthesis of biologically active 2-substituted benzimidazole derivatives
Chandra, Ramesh,Hooda, Sunita,Kohli, Sahil,Rathee, Garima
, p. 7750 - 7758 (2021/06/16)
This work is generally focused on the synthesis of an efficient, reusable and novel heterogeneous Al2O3/CuI/PANI nanocatalyst, which has been well synthesized by a simple self-assembly approach where aniline is oxidized into PANI and
Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature
Mathapati, Sushil R.,Patil, Komal N.,Mathakari, Sujit S.,Suryawanshi, Appasaheb W.,Jadhav, Arvind H.
, p. 538 - 547 (2021/01/21)
The present work describes synthesis of a series of benzimidazoles, benzoxazoles and benzothiazoles through the cyclization of 1, 2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, aliphatic and heteroaryl aldehydes. The present synthetic protocol is very much efficient in presence of 5 mol % fluorophosphoric acid as a catalyst in ethanol solvent at room temperature. Shorter reaction time, simple work-up technique, high yields and easy availability are specific compensations of the present synthetic approach.
Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity
Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal
supporting information, p. 340 - 349 (2020/12/01)
An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.
Preparation method 2 -substituted benzimidazole derivative
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Paragraph 0077-0082, (2021/11/10)
The invention belongs to the field of fine chemical product production, and particularly relates to 2 -substituted benzimidazole derivative preparation method which comprises the following steps: (1) taking O-phenylenediamine and aldehyde as raw materials, carrying out catalytic condensation, cyclization and oxidation reaction in a eutectic solvent. (2) Water is added to the reaction system, the separated product is filtered, and the eutectic solvent is recycled. (3) After recrystallization, a target product is obtained. The method has the advantages of simple operation process, easily available raw materials, low cost, high purity of the target product and no catalyst participation, can effectively prevent isomer formation, and is beneficial to large-scale production.
