- Design, synthesis, molecular docking and cytotoxic evaluation of novel 2-furybenzimidazoles as VEGFR-2 inhibitors
-
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.
- 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.
-
-
Read Online
- Synthesis and anomeric configuration of 2-(erythrofuranosyl)benzimidazole C-nucleoside analogues
-
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.
- Sallam, Mohammed A. E.,Ibrahim, El-Sayed I.,El-Eter, Khaled A.A.,Cassady, John M.
-
-
Read Online
- [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study
-
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.
- Brahman, Dhiraj,Chhetri, Sailesh,Kamath, Amarjit,McArdle, Patrick,Sinha, Biswajit
-
-
- Preparation method of 2-substituted benzimidazole compound
-
The invention discloses a preparation method of a 2-substituted benzimidazole compound, and belongs to the field of synthesis of benzimidazole compounds. The 2-substituted benzimidazole compound is synthesized in an organic solvent by taking an o-nitroaniline compound, aromatic aldehyde, o-dinitrobenzene and aromatic aldehyde as raw materials and taking Co particles wrapped by a nitrogen-doped carbon material as a catalyst. According to the method, the 2-substituted benzimidazole compound can be prepared at room temperature, the reaction conditions are mild, the yield is as high as 95%, the selectivity is as high as 99%, and the method is economical, environmentally friendly and wide in substrate applicability. The used catalyst is easy to prepare, low in cost and good in reusability, canbe separated by utilizing magnetism, and is convenient to recover, so that the method has a relatively strong industrial application prospect.
- -
-
Paragraph 0084-0088
(2021/02/20)
-
- A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
-
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.
- Bhatt, Ashish,Kant, Ravi,Kumar, Sonu,Reddy, Yella,Sarmah, Manash P.
-
-
- H2 Activation with Co Nanoparticles Encapsulated in N-Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles
-
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.
- Lin, Chuncheng,Wan, Weihao,Wei, Xueting,Chen, Jinzhu
-
p. 709 - 720
(2020/11/30)
-
- A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst
-
This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is
- Vasu, Amrutham,Naresh, Mameda,Krishna Sai, Gajula,Divya Rohini, Yennamaneni,Murali, Boosa,Ramulamma, Madasu,Ramunaidu, Addipilli,Narender, Nama
-
p. 9439 - 9446
(2021/12/09)
-
- Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
-
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.
- Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
-
p. 6705 - 6716
(2021/12/31)
-
- s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles
-
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.
- 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)
-
- Al2O3/CuI/PANI nanocomposite catalyzed green synthesis of biologically active 2-substituted benzimidazole derivatives
-
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
- Chandra, Ramesh,Hooda, Sunita,Kohli, Sahil,Rathee, Garima
-
p. 7750 - 7758
(2021/06/16)
-
- Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature
-
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.
- Mathapati, Sushil R.,Patil, Komal N.,Mathakari, Sujit S.,Suryawanshi, Appasaheb W.,Jadhav, Arvind H.
-
p. 538 - 547
(2021/01/21)
-
- Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity
-
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.
- Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal
-
supporting information
p. 340 - 349
(2020/12/01)
-
- Preparation method 2 -substituted benzimidazole derivative
-
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.
- -
-
Paragraph 0077-0082
(2021/11/10)
-
- Photochemical Synthesis of Benzimidazoles from Diamines and Aldehydes
-
An efficient, green, cheap, and metal-free photochemical protocol for the synthesis of benzimidazoles has been developed. 2,2-Dimethoxy-2-phenylacetophenone was employed as the photoinitiator and CFL lamps were used as the light source, leading to the cyc
- Skolia, Elpida,Apostolopoulou, Mary K.,Nikitas, Nikolaos F.,Kokotos, Christoforos G.
-
supporting information
p. 422 - 428
(2020/12/13)
-
- Nickel catalysed construction of benzazoles: Via hydrogen atom transfer reactions
-
Herein we report a homogeneous, phosphine free, inexpensive nickel catalyst that forms a wide variety of benzazoles from alcohol and diamines by a reaction sequence of alcohol oxidation, imine formation, ring cyclization and dehydrogenative aromatization. A reversible azo/hydrazo couple, that is part of the ligand architecture steers both the alcohol oxidation and dehydrogenation of the annulated amine under fairly mild reaction conditions. Interestingly, both the alcohol oxidation and amine dehydrogenation steps are directly mediated by hydrogen atom transfer (HAT), which is greatly facilitated by the reduced ligand backbone. The kH/kD for the amine dehydrogenation step, measured at 60 °C is 5.9, fully consistent with HAT as the rate determining factor during this step. This is a unique scenario where two consecutive oxidation steps towards benzazole formation undergo HAT, which has been substantiated via kinetic studies, KIE determination and intermediate isolation. This journal is
- Adhikari, Debashis,Bains, Amreen K.,Dey, Dhananjay,Kundu, Abhishek,Yadav, Sudha
-
p. 6495 - 6500
(2020/11/13)
-
- A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o-phenylenediamines catalyzed by [MIMPs]+Cl-/NaNO2/TEMPO
-
The ionic liquid 1-methyl-3-(3-sulfopropyl)imidazolium chloride ([MIMPs]+Cl-) in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and sodium nitrite (NaNO2) as a catalytic system demonstrates high efficiency in the one-pot two-step aerobic oxidative condensation of benzyl alcohols with 1,2-phenylenediamines to give benzimidazoles. Various benzimidazoles are obtained in good to excellent yields by this strategy.
- Geng, Zhenzhen,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
-
p. 557 - 565
(2020/03/30)
-
- Development of a fluorescent chemosensor for chloride ion detection in sweat using Ag+-benzimidazole complexes
-
The level of chloride ions (Cl?) in sweat is a recognized biomarker for the genetic disorder cystic fibrosis (CF). The accurate quantitation of chloride ions in sweat is therefore a vital diagnostic tool for this life-threatening disease. In this work, a fluorescent, chloride ion chemosensor was developed by exploiting the strong interaction between silver (Ag+) and chloride ions. Using the concept of ligand displacement, six Ag+-benzimidazole complexes were prepared as candidate chloride ion chemosensors. The Ag+-2-(Furan-2-yl)-1H-benzo[d]imidazole (Ag+-FBI) complex was identified as the optimal sensor owing to its Ag+-FBI high sensitivity (limit of detection = 19 μM), short response time (+-FBI complex exhibited high selectivity for Cl? ions and was successfully used to quantify chloride ions in artificial sweat samples containing multiple ions and other biological constituents. This unique, simple, and effective probe thus shows great potential for clinical diagnostic applications.
- Han, Min Su,Jung, Minhyuk,Kim, Jaewon,Kim, Sudeok,Lee, Hohjai,Lee, Suji
-
-
- "Metal-Free" Nanoassemblies of AIEE-ICT-Active Pyrazine Derivative: Efficient Photoredox System for the Synthesis of Benzimidazoles
-
Supramolecular nanoassemblies of an AIEE-ICT-active pyrazine derivative (TETPY) having strong absorption in the visible region and excellent transportability have been utilized as an efficient photoredox catalytic system for the synthesis of a variety of benzimidazoles having electron-withdrawing/electron-releasing/aliphatic groups under "metal-free"conditions. The reaction protocol involves the successful harvesting of visible light by TETPY assemblies to catalyze the coupling of o-phenylenediamine/substituted diamines and substituted aromatic/heterocyclic/aliphatic aldehydes under aerial conditions using mixed aqueous media as the reaction solvent. TETPY assemblies could activate aerial oxygen to generate superoxide for completing the vital proton abstraction step without the need for any external metal/base/oxidant. Moreover, all the products are purified by recrystallization from organic solvents. The TETPY assemblies also exhibited high efficiency in catalyzing the synthesis of 2-substituted benzothiazoles and quinazolines in excellent yields.
- Dadwal, Shruti,Kumar, Manoj,Bhalla, Vandana
-
p. 13906 - 13919
(2020/11/20)
-
- Synthesis of quinoxaline, benzimidazole and pyrazole derivatives under the catalytic influence?of biosurfactant-stabilized iron nanoparticles in water
-
Abstract: We have reported the synthesis, characterization, and catalytic applications of amorphous iron nanoparticles (FeNPs) using aqueous leaves extract of renewable natural resource Boswellia serrata plant. Synthesized FeNPs were stabilized in situ by the addition of aqueous pod extracts of Acacia concinna as a biosurfactant (pH 3.11). The structural investigation of biosynthesized nanoparticles was performed using UV–visible spectroscopy, X-ray diffraction analysis, selected area electron diffraction, energy-dispersive X-ray spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy, thermogravimetric analysis, and BET analysis. The FeNPs were amorphous in nature with average particle size ~ 19?nm and successfully employed as heterogeneous catalyst for the synthesis of quinoxaline, benzimidazole, and pyrazole derivatives in aqueous medium at ambient conditions. The FeNPs could be recycled up to five times with modest change in the catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
- Arde, Satyanarayan M.,Patil, Audumbar D.,Mane, Ananda H.,Salokhe, Prabha R.,Salunkhe, Rajashri S.
-
p. 5069 - 5086
(2020/09/02)
-
- tert-Butyl nitrite catalyzed synthesis of benzimidazoles from o-phenylenediamine and aldehydes at room temperature
-
A simple and efficient method is demonstrated for the synthesis of benzimidazoles via cyclocondensation of o-phenylenediamine with aldehydes in the presence of catalytic amount of tert-butyl nitrite. All the reactions were carried out at room temperature while the desired products were obtained in good to excellent yields.
- Azeez, Sadaf,Chaudhary, Priyanka,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri
-
supporting information
(2020/02/22)
-
- Catalytic activity of Co(II) Salen&at;KCC-1 on the synthesis of 2,4,5-triphenyl-1H-imidazoles and benzimidazoles
-
The synthesis, reactions and biological properties of imidazoles and benzimidazole make up the bulk of the ring chemistry. In this study, the reaction between different types of aromatic aldehydes and ammonium acetate with diphenylethanedione, in ethanol solvent, using the Co(II) Salen complex&at;KCC-1 catalyst which is produced from Co (II) complex which is supported onto the KCC-1 was studied. The results showed that the products were synthesized in good to excellent yields. The products were identified with IR and NMR spectroscopy. Also, the catalyst was identified by FT-IR, TGA, TEM, and XRD. Finally, the catalyst was reused several times without lack of catalytic activity.
- Ali Nasseri, Mohammad,Allahresani, Ali,Naghdi, Elaheh
-
-
- Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
-
A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
- Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
-
-
- Skin damages—Structure activity relationship of benzimidazole derivatives bearing a 5-membered ring system
-
In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three cl
- Baldisserotto, Anna,Balzarini, Jan,Djuidje, Ernestine Nicaise,Durini, Elisa,Liekens, Sandra,Manfredini, Stefano,Sciabica, Sabrina,Serra, Elena,Vertuani, Silvia
-
-
- Cobalt-Catalyzed Sustainable Synthesis of Benzimidazoles by Redox-Economical Coupling of o-Nitroanilines and Alcohols
-
This study reveals cobalt-catalyzed sustainable synthesis of benzimidazoles by redox-economical coupling of o-nitroanilines and alcohols. The major advantage of this report is the use of a commercially available cheap cobalt catalyst to produce a wide variety of 2-substituted benzimidazoles by hydrogen autotransfer without using any additional external redox reagent and costly ligand system. A thorough mechanistic insight of the reaction is proposed by performing a series of control experiments.
- Das, Sanju,Mallick, Samrat,De Sarkar, Suman
-
p. 12111 - 12119
(2019/10/02)
-
- Development of titania-supported iridium catalysts with excellent low-temperature activities for the synthesis of benzimidazoles via hydrogen transfer
-
Titania-supported iridium catalysts which enable the synthesis of benzimidazoles from 2-nitroaniline and primary alcohols under mild conditions have been developed. The iridium catalysts supported on {010}/{101}-faceted anatase (PA-135-3.5) showed the excellent activity in spite of their moderate surface areas, while there is a positive correlation between BET surface area and the activity of iridium catalysts. TEM analysis revealed the formation of small iridium nanoparticles (mean diameter; 1.0 nm) on PA-135-3.5, which would be one reason for the excellent catalytic activity. According to the XPS study, relatively high-valent iridium species would be responsible for the catalysis. Various primary alcohols bearing electron-withdrawing or electron-donating groups were applicable. The removal of the solid catalyst by the hot filtration completely stopped further progress of the reaction, indicating that the catalyst acted heterogeneously. The catalysts could be recycled, and there was no leaching of iridium species into the solution.
- Fukutake, Tatsuhiro,Wada, Kenji,Yu, Han,Hosokawa, Saburo,Feng, Qi
-
-
- Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water
-
Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.
- Chakrabarti, Kaushik,Maji, Milan,Kundu, Sabuj
-
supporting information
p. 1999 - 2004
(2019/04/27)
-
- Visible-light-induced condensation cyclization to synthesize benzimidazoles using fluorescein as a photocatalyst
-
A mild strategy for visible-light-induced synthesis of benzimidazoles was developed using aromatic aldehydes and o-phenylenediamines as substrates. The use of an organic dye, fluorescein, as an innoxious photocatalyst provided a mild and inexpensive catalytic system to synthesize a series of benzimidazoles in moderate to excellent yields. It was originally applied to this system to obtain benzimidazoles. Besides, the catalytic system does not require an additional oxidant or metal which was good for the environment.
- Li, Zhuofei,Song, He,Guo, Rui,Zuo, Minghui,Hou, Chuanfu,Sun, Shouneng,He, Xin,Sun, Zhizhong,Chu, Wenyi
-
p. 3602 - 3605
(2019/07/09)
-
- Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation
-
The development of a metal-free protocol for transformations in organic synthesis offers a significant potential environmental benefit. This article reports the exploration of meglumine, a nontoxic and biodegradable amino sugar, as an organocatalyst for the synthesis of biologically active 1H-dibenzo[b,e][1,4]diazepin-1-ones, highly regioselective benzimidazole derivatives and derivatives of quinoxalines. Operational simplicity, mild reaction conditions, shorter reaction times, and use of green solvents are the highlights of this protocol. The advantage of ultrasonic irradiation has been significantly explored for the synthesis of the aforesaid compounds. Furthermore, the multifaceted use of o-phenylenediamine has also been accentuated in the study.
- Nongrum, Ridaphun,Kharmawlong, George Kupar,Rani, Jims World Star,Rahman, Noimur,Dutta, Arup,Nongkhlaw, Rishanlang
-
-
- A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
-
A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
- Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
-
p. 934 - 944
(2019/06/13)
-
- Inhibition of aflatoxin B1 biosynthesis and down regulation of aflR and aflB genes in presence of benzimidazole derivatives without impairing the growth of Aspergillus flavus
-
Aflatoxins are mutagenic secondary metabolites produced by certain ubiquitous saprophytic fungi. These contaminate agricultural crops and pose a serious health threat to humans and livestock all over the world. Benzimidazole and its derivatives are biologically active heterocyclic compounds known for their fungicidal activity. In the present study, second and sixth position substituted benzimidazole derivatives are tested for their antifungal and anti-aflatoxigenic activity. Aflatoxigenic strain of Aspergillus flavus cultured in Yeast extract sucrose (YES) medium as well as in rice in the presence and absence of test compounds. 2-(2-Furyl) benzimidazole (FBD) showed complete inhibition of fungal growth at 50 μg/mL. However, the polar derivatives of FBD viz. 6-NFBD, 6-AFBD, 6-CAFBD, and 6-CFBD did not impair the fungal growth but effectively inhibited aflatoxin B1 biosynthesis. Significant down-regulation of aflR gene involved in regulation and aflB structural gene for aflatoxin B1 biosynthesis was observed in presence of 6-NFBD. These benzimidazole derivatives also showed good anti-aflatoxigenic activity in rice, though the IC50 concentrations in rice were comparatively higher than those in YES medium. This study summarizes the most notable structure-activity relationship (SAR) of 2-(2-Furyl) benzimidazoles for anti-aflatoxigenic and anti-fungal activities. These molecules can be further studied for their applications in industrial fermentation processes vulnerable to mold growth and subsequent aflatoxin B1 synthesis like koji fermentation, cheese production, etc.
- Dhanamjayulu,Boga, Ramesh Babu,Mehta, Alka
-
-
- Iron(III)–salen complex on a polymer scaffold as heterogeneous catalyst for synthesis of benzimidazoles
-
Benzimidazoles are important bioactive compounds with diverse applications in the medicinal, industrial, as well as agrochemical fields. In this study, an iron–salen complex on a polymer scaffold was synthesized and characterized, and its performance asse
- Balinge, Kamlesh Rudreshwar,Datir, Sagar Krushnarao,Khajone, Vijay Baburao,Bhansali, Karan Jivanlal,Khiratkar, Avinash Ganesh,Bhagat, Pundlik Rambhau
-
p. 155 - 168
(2018/09/25)
-
- Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Br?nsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles
-
A novel efficient method for the selective synthesis of 2-substituted benzimidazoles is described through condensation reaction of o-phenylenediamines with a wide rang of aliphatic, aromatic and heteroaromatic aldehyde substrates using Br?nsted acidic ionic liquid as a reusable catalyst under metal-free conditions at ambient temperature. Notably, Dodecylimidazolium hydrogen sulfate ([DodecIm][HSO4]) is the most efficient catalyst for good to excellent yields of the corresponding products (up to 98%). Subsequently, this protocol was successfully applied for the preparation of N-alkylated 1,2-disubstituted benzimidazoles in high to excellent yields via sequential one-pot reaction. In addition, catalysts are recycled at least four times without significant loss in activity.
- Senapak, Warapong,Saeeng, Rungnapha,Jaratjaroonphong, Jaray,Promarak, Vinich,Sirion, Uthaiwan
-
p. 3543 - 3552
(2019/05/29)
-
- Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon
-
A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.
- Wang, Zhaozhan,Song, Tao,Yang, Yong
-
supporting information
p. 319 - 324
(2019/02/12)
-
- Synthesis of benzimidazoles by Cul-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water
-
An efficient copper-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde for the synthesis of benzimidazoles with 1,10-phenanthroline as the ligand has been developed. A variety of substituted benzimidazole derivatives can be obtained in yields up to 95%.
- Ke, Fang,Zhang, Peng,Lin, Chen,Lin, Xiaoyan,Xu, Jianhua,Zhou, Xiangge
-
supporting information
p. 8090 - 8094
(2018/11/23)
-
- C-N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N-Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines
-
Ruthenium nanoparticles (NPs) supported on N-doped carbon (Ru/N?C) were prepared by the pyrolysis of cis-Ru(phen)2Cl2 loaded onto carbon powder (VULCAN XC72R) at 800 °C. Ru/N?C NPs (0.2 mol% Ru) selectively catalyzed either acceptorless dehydrogenation coupling (ADC) or auto-transfer-hydrogen (ATH) reactions of amines with alcohols to imines and secondary amines. Such selectivity could be controlled by the choice of alkali metal ion associated with the base. Under similar catalytic conditions, the ADC cross-coupling of diamines with primary alcohols or diols afforded the corresponding benzimidazoles and quinoxalines in good to excellent yields. This catalytic system displayed good activity, recyclability, and wide applicability to a diverse range of substrates.
- Guo, Bin,Li, Hong-Xi,Zhang, Shi-Qi,Young, David James,Lang, Jian-Ping
-
p. 5627 - 5636
(2018/12/04)
-
- An efficient NaHSO3-promoted protocol for chemoselective synthesis of 2-substituted benzimidazoles in water
-
An efficient protocol for chemoselective synthesis of 2-substituted benzimidazoles from a variety of aliphatic/aromatic/ heteroaryl aldehydes and o-phenylenediamine derivatives promoted by NaHSO3 in water had been developed. The amount of NaHSO3 had a great effect on the reaction selectivity of 2-substituted benzimidazole and 1,2-disubstituted benzimidazole when the reaction was carried out in water. When the amount of the NaHSO3 was more than 11 equivalents, the 2-substituted benzimidazole could be highly selectively formed as the sole product. NaHSO3 was firstly reacted with aldehyde to form the aldehyde sodium bisulfite, which reacted with o-phenylenediamine to form the 2-substituted benzimidazole and inhibited the formation of 1,2-disubstituted benzimidazole. This protocol solved the poor selectivity problem appearing in traditional method when cyclocondensation between o-phenylenediamine and aldehydes. The method also had advantage of simple work up by filtrating the single 2-substituted benzimidazole precipitates from reaction mixture at the end of the reaction without further purification. In addition, the method was applicable to both electron-rich and electron-poor starting materials, which was successfully used for synthesizing nine novel 2-substituted benzimidazole derivatives containing a 1,2,3-triazole moiety. They were characterized by NMR, IR and HRMS spectrum. Moreover, this method had been applied to a large scale synthesis of 2-substituted benzimidazole derivatives.
- Jiang, Yu-Qin,Jia, Shu-Hong,Li, Xi-Yong,Sun, Ya-Min,Li, Wei,Zhang, Wei-Wei,Xu, Gui-Qing
-
p. 1265 - 1276
(2019/01/28)
-
- Sulfonic-acid-functionalized activated carbon made from tea leaves as green catalyst for synthesis of 2-substituted benzimidazole and benzothiazole
-
Abstract: A simple and efficient procedure for synthesis of 2-substituted benzimidazole and benzothiazole has been developed by using sulfonic-acid-functionalized activated carbon as heterogeneous catalyst. The activated material was prepared from matured tea leaf in presence of phosphoric acid as activating agent. The final catalyst was prepared by anchoring –SO3H group on the surface of the activated carbon. The catalyst could be easily recovered and reused for more than three catalytic cycles without significant loss in catalytic activity. The catalytic performance of the catalyst was found to be superior to that of a similar catalyst prepared from montmorillonite K10. Graphical Abstract: [Figure not available: see fulltext.].
- Goswami, Mridusmita,Dutta, Mintu Maan,Phukan, Prodeep
-
p. 1597 - 1615
(2017/11/17)
-
- COMPOSITION FOR INHIBITING SYNTHESIS OF MYCOTOXIN WITHOUT AFFECTING THE GROWTH OF THE FUNGI
-
A composition for inhibiting the growth of mycotoxins without affecting the growth of fungi is provided. The mycotoxin is an Aflatoxin and the fungus is an Aspergillus. The anti-aflatoxin composition comprises benzimidazole derivatives of Formula, where the A is hydrogen or C1-C6 alkyl or C6-C14 aryl; B is C1-C10 alkyl or C6-C14 aryl or oxygen, sulfur, nitrogen containing heteroaryl; C and D are hydrogen or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl; E is hydrogen or nitro or cyano or carboxyl or acetamidoxime or amidoxime or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl or oxygen, sulfur, and nitrogen containing heteroaryl; F is hydrogen or C1-C6 alkyl or C1-C6 alkoxyl or C6-C14 aryl or oxygen, sulfur, and nitrogen containing heteroaryl, and mixture thereof with corresponding salts.
- -
-
Paragraph 0067
(2018/11/24)
-
- p-Toluenesulfonic acid coated natural phosphate as an efficient catalyst for the synthesis of 2-substituted benzimidazole
-
2-Substituted benzimidazoles are selectively synthesised in high yields via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of p-toluenesulfonic acid coated natural phosphate (NP/PTSA) under mild conditions. The use of NP/PTSA as a reusable catalyst makes this process simple, convenient, and environmentally friendly.
- Belkharchach, Soumia,Elayadi, Hanane,Ighachane, Hana,Sebti, Said,Ali, Mustapha Ait,Lazrek, Hassan B.
-
p. 614 - 617
(2018/12/13)
-
- Concentrated solar radiation promoted unconventional greener approach: Solvent-free benign synthesis of functionalized benzimidazoles
-
Renewable concentrated solar-radiation (CSR) offered a promising en route for the development of practical, highly efficient, scalable, catalyst free and solvent-free clean process leading to the synthesis of functionalized benzimidazoles. Developed protocol has a very good substrate scope, involves mild reaction conditions and products obtained in good to excellent yields. Method presented the observations in which light alone could affect the remarkable changes with more than 85% energy saving and 75% less reaction time in listed organic transformations.
- Harsh, Simran,Yusuf, Mohamad,Sharma, Rohit,Kumar, Yogesh,Kumar, Rupesh
-
p. 119 - 130
(2018/10/26)
-
- Practical application of PhI(OAc)2/I2 combination to synthesize benzimidazoles from 2-aminobenzylamine through ring distortion strategy
-
In this present work the combination of iodobenzenediacetate (PIDA)/iodine has been established as a promising reagent to promote the construction of 2-substituted benzimidazoles from 2-aminobenzylamine and a variety of easily available aldehydes/arylamines through a ring distortion strategy. The present protocol offers mild, metal free, robust conditions to synthesize 2-substituted benzimidazoles in good to excellent yields. In addition, the oxidation prone functional groups show tolerance during the reaction and after completion of the reaction pure products can be easily obtained applying hassle free filtration of the reaction mixture through silica gel bed.
- Saha, Moumita,Mukherjee, Prasun,Das, Asish R.
-
p. 1046 - 1049
(2017/03/31)
-
- Preparation method of indazole and application of indazole in medicine synthesis
-
The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.
- -
-
-
- Direct conversion of alkyl halides into benzimidazoles using pyridine-N-oxide and 1,2-diaminobenzenes
-
Benzimidazole heterocycles were obtained from halogenated compounds and aromatic 1,2-diamines. A mild oxidizing reagent such as pyridine N-oxide (PyO) is required to produce the benzimidazole core. The method is solvent free and provides products without the need for chromatography. Good yields, moderate reaction temperature, fast reaction rates are important advantages of this procedure. {figure presented}.
- Bratulescu, George
-
-
- Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
-
The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.
- Zhang, Ruipu,Qin, Yan,Zhang, Long,Luo, Sanzhong
-
supporting information
p. 5629 - 5632
(2017/10/25)
-
- Effect of Cd-doping on the catalytic activity of ZnO nanoflakes in the synthesis of benzimidazoles
-
Abstract: A set of hierarchical CdxZn1?xO nanoflakes (x?=?0, 0.01 and 0.03) was prepared by the co-precipitation method using methanol as solvent. The prepared samples were characterized by UV–visible, X-ray diffraction, field emissi
- Kunde, Sachin P.,Kanade, Kaluram G.,Karale, Bhausaheb K.,Akolkar, Hemantkumar N.,Randhavane, Pratibha V.,Shinde, Santosh T.
-
p. 7277 - 7290
(2017/10/06)
-
- Magnetic nanoparticle-supported DABCO tribromide: A versatile nanocatalyst for the synthesis of quinazolinones and benzimidazoles and protection/deprotection of hydroxyl groups
-
1,4-Diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles (MNPs-DABCO tribromide) as a novel heterogeneous tribromide type compound was found to be an efficient and reusable nanocatalyst for the one-pot synthesis of 2-arylquinazolin-4(3H)-ones and 2-aryl-1H-benzo[d]imidazoles through oxidative cyclization of aldehydes with 2-aminobenzamides and 1,2-phenylenediamine, respectively. Also, MNPs-DABCO tribromide catalyzed trimethylsilylation/tetrahydropyranylation and desilylation/depyranylation of a wide variety of alcohols and phenols through changing the solvent medium at room temperature.
- Rostami, Amin,Pourshiani, Omid,Navasi, Yahya,Darvishi, Neda,Saadati, Shaghayegh
-
p. 9033 - 9040
(2017/08/29)
-
- A practical green synthesis and biological evaluation of benzimidazoles against two neglected tropical diseases: Chagas and leishmaniasis
-
Antimicrobial resistance is an ever-increasing problem throughout the world and has already reached severe proportions. Two very common neglected tropical diseases are Chagas' disease and leishmaniasis. Chagas' disease is a severe health problem, mainly in Latin America, causing approximately 50000 deaths a year and millions of people are infected. About 25-30% of the patients infected with Trypanosoma cruzi develop the chronic form of the disease. On the other hand, Leishmaniasis represents complex diseases with an important clinical and epidemiological diversity. It is endemic in 88 countries 72 of which are developing countries and it has been estimated that are 12 million people infected and 350 million are in areas with infection risk. On this basis, research on organic compounds that can be used against these two diseases is an important target. A very simple, green, and efficient protocol is developed in which bismuth nitrate pentahydrate is employed as a Lewis acid catalyst in aqueous media under microwave irradiation for the synthesis of various 2-aryl substituted benzimidazoles from aldehydes and o-phenylenediamine. Other salient features of this protocol include milder conditions, atom-economy, easy extraction, and no wastes. Nine 1H-benzimidazole derivatives (1-9) with substituents at positions 2 and 5 were synthesized and the structure of the compounds was elucidated by spectroscopic methods. The compounds were screened to identify whether they posses pharmacological activity against Chagas' disease and leishmaniasis. Compound 8 showed better activity than the control Nifurtimox against INC-5 Trypanosoma cruzi strain whereas compounds 3 and 9 have demonstrated potent leshmanicidal activity. A systematic green synthetic procedure and in vitro biological evaluation of nine 1H-benzimidazoles are described.
- Bandyopadhyay, Debashis,Samano, Selina,Villalobos-Rocha, Juan Carlos,Sanchez-Torres, Luvia Enid,Nogueda-Torres, Benjamin,Rivera, Gildardo,Banik, Bimal K.
-
p. 4714 - 4725
(2018/02/14)
-
- Facile and efficient aerobic one-pot synthesis of benzimidazoles using Ce(NO3)3·6H2O as promoter
-
A series of 2-substituted benzimidazoles was synthesized under aerobic conditions, by simply heating 1,2-diaminobenzene and aldehydes in DMF at 80 °C, employing Ce(NO3)3·6H2O as promoter and atmospheric air as an efficient oxidant. The procedure afforded the products from good to excellent yields. Furthermore, this new economic and eco-friendly protocol avoids the use of toxic metal catalysts, as well as additional bases and oxidants.
- Martins, Guilherme M.,Puccinelli, Thiago,Gariani, Rogério A.,Xavier, Fernando R.,Silveira, Claudio C.,Mendes, Samuel R.
-
supporting information
p. 1969 - 1972
(2017/04/27)
-
- In water–ultrasound-promoted synthesis of tetraketones and 2-substituted-1H-benzimidazoles catalyzed by BiOCl nanoparticles
-
A highly efficient, green protocol has been developed for the synthesis of various structurally diverse 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 2-substituted-1H-benzimidazole derivatives. The reaction was performed in water under ultrasound irradiation, using BiOCl nanoparticles as a catalyst. The nanocatalyst was found to be reusable for seven subsequent reactions without much loss in activity. Simple methodology with short reaction times and mild reaction conditions with easy work-up procedure are the salient features of this method.
- Sapkal, Bharatkumar M.,Labhane, Prakash K.,Satam, Jitendra R.
-
p. 4967 - 4979
(2017/07/22)
-
- Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles
-
An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.
- Tang, Meng,Kong, Yuanfang,Chu, Bingjie,Feng, Dan
-
p. 926 - 939
(2016/04/05)
-