94-52-0Relevant academic research and scientific papers
Homology modelling, molecular dynamics simulation and docking evaluation of β-tubulin of Schistosoma mansoni
El-Shehabi, Fouad,Mansour, Basem,Bayoumi, Waleed A.,El Bialy, Serry A.,Elmorsy, Mohammad A.,Eisa, Hassan M.,Taman, Amira
, (2021/09/16)
Schistosomiasis is one of the neglected diseases causing considerable morbidity and mortality throughout the world. Microtubules with its main component, tubulin play a vital role in helminthes including schistosomes. Benzimidazoles represent potential drug candidates by binding β-tubulin. The study aimed to generate a homology model for the β-tubulin of S. mansoni using the crystal structure of O vis aries (Sheep) β-tubulin (PDB ID: 3N2G D) as a template, then different β-tubulin models were generated and two previously reported benzimidazole derivatives (NBTP-F and NBTP-OH) were docked to the generated models, the binding results indicated that both S. mansoni, S. haematobium were susceptible to the two NBTP derivatives. Additionally, three mutated versions of S. mansoni β-tubulin wild-type were generated and the mutation (F185Y) seems to slightly enhance the ligand binding. Dynamics simulation experiments showed S. haematobium β-tubulin is highly susceptible to the tested compounds; similar to S. mansoni, moreover, mutated models of S. mansoni β-tubulin altered its NBTPs susceptibility. Moreover, additional seven new benzimidazole derivatives were synthesized and tested by molecular docking on the generated model binding site of S. mansoni β-tubulin and were found to have good interaction inside the pocket.
A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles
Li, Hu,Li, Zhengyi,Wu, Hongguo,Yang, Song,Yu, Zhaozhuo,Zhang, Lilong,Zhu, Kaixun
supporting information, p. 5759 - 5765 (2021/08/23)
Chemocatalytic upgrading of the greenhouse gas CO2 to valuable chemicals and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO2 with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO2) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO2 reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25 °C, 1 atm CO2) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO2 was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO2 could supply CO2 by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Experimental and computational studies showed that the carboxyl species on NHC-CO2 was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO2 during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production.
Method for synthesizing benzimidazole from carbon dioxide and o-phenylenediamine compound
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Paragraph 0041-0044, (2021/06/06)
The invention discloses a method for synthesizing benzimidazole from carbon dioxide and an o-phenylenediamine compound, the method is characterized in that an amino-containing functionalized ordered mesoporous polymer is used as a catalyst, o-phenylenediamine and carbon dioxide are used as raw materials, dimethylaminoborane is used as a hydrogen reduction reagent, carbon dioxide and the o-phenylenediamine compound are catalyzed to react in an NMP solvent to generate a benzimidazole compound, wherein the dosage of a catalyst is 0.01-1mol% based on the nitrogen content of the o-phenylenediamine compound; the filling pressure of the carbon dioxide is 0.1-2MPa; the reaction temperature is 60-180DEG C; the molar ratio of the catalyst to the NMP is 1:50-100. Compared with the prior art, the catalyst has the advantages of simple preparation, high catalytic activity, capability of catalyzing the reaction of carbon dioxide and the o-phenylenediamine compound under mild conditions to generate benzimidazole and derivatives thereof, and the like.
Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives
Han, Limin,Hong, Hailong,Li, Xiao,Yang, Yue,Zhang, Junhua,Zhu, Ning
supporting information, (2021/09/28)
A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.
Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon
Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal
supporting information, p. 3754 - 3759 (2021/10/14)
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR
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Paragraph 0590; 0591, (2020/06/16)
Disclosed is a class of new aryl-phosphorus-oxygen compounds as shown in formula (I) as EGFR kinase inhibitors, and pharmaceutically acceptable salts thereof.
A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei
supporting information, (2020/10/05)
A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.
Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides
Chen, Fen-Er,Dong, Lin,Li, Hongyan,Liu, Jinxin,Luo, Liangliang,Xiao, You-Cai,Zhou, Yuan
, p. 29257 - 29262 (2020/10/02)
A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is
