934-22-5Relevant academic research and scientific papers
5,5′-Dibenzoimidazole as building block for a new 3D Co(II) coordination polymer: A combined EPR and DFT study using UB3LYP model
Datta, Amitabha,Massera, Chiara,Garribba, Eugenio,Frontera, Antonio
, p. 473 - 479 (2019)
A new Co(II) three-dimensional coordination polymer, [Co(L)(L′)]n (1) [where L = 5,5′-dibenzoimidazole, and L′ = doubly deprotonated terephthalic acid] has been synthesized hydro(solvo)thermally and its molecular and crystal structure have been elucidated through single crystal X-ray diffraction analysis. Each Co(II) ion displays a slightly distorted trigonal bipyramidal geometry, the apical positions being occupied by the nitrogen atoms of two symmetry-related dibenzoimidazole ligands, while the oxygen atoms from three distinct terephthalic acids are in the equatorial plane. Considering the Co2C2O6 dimeric moieties as nodes, and the ancillary ligands as connectors, the structure can be simplified as a 8-c uninodal net of the type bcu, body centered cubic, with point symbol {424·64} and vertex symbol [4·4·4·4·4·4·4·4·4·4·4·4·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·4(3)·*·*·*·*]. The EPR spectra for 1 have been reported, showing g|| = 2.176 and g⊥ = 2.052 at RT (room temperature), and g|| = 2.172 and g⊥ = 2.060 at LNT (liquid nitrogen temperature). Finally, the electronic nature of the molecular geometry of 1 has been explored by DFT computation applying the UB3LYP/def2-TZVP level of theory, showing the energy difference between the high spin and low spin configurations.
Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes
Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao
, (2022/01/11)
The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).
Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex
Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.
, p. 2895 - 2906 (2021/02/27)
We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.
Molecular design, synthesis and in vitro biological evaluation of thienopyrimidine–hydroxamic acids as chimeric kinase HDAC inhibitors: a challenging approach to combat cancer
Abdel-Atty, Mona M.,Abouzid, Khaled A. M.,Farag, Nahla A.,Mowafy, Samar,Serya, Rabah A. T.
, p. 1290 - 1312 (2021/07/09)
A series of thieno[2,3-d]pyrimidine-based hydroxamic acid hybrids was designed and synthesised as multitarget anti-cancer agents, through incorporating the pharmacophore of EGFR, VEGFR2 into the inhibitory functionality of HDAC6. Three compounds (12c, 15b and 20b) were promising hits, whereas (12c) exhibited potent VEGFR2 inhibition (IC50=185 nM), potent EGFR inhibition (IC50=1.14 μM), and mild HDAC6 inhibition (23% inhibition). Moreover, compound (15c) was the most potent dual inhibitor among all the synthesised compounds, as it exhibited potent EGFR and VEGFR2 inhibition (IC50=19 nM) and (IC50=5.58 μM), respectively. While compounds (20d) and (7c) displayed nanomolar selective kinase inhibition with EGFR IC50= 68 nM and VEGFR2 IC50= 191 nM, respectively. All of the synthesised compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumour cell lines. Additionally, molecular docking studies and ADMET studies were carried out to gain further insight into their binding mode and predict the pharmacokinetic properties of all the synthesised inhibitors.
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.
ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I' PATHWAY AND METHODS OF USE THEREOF
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Page/Page column 56, (2020/03/05)
The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.
ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I" PATHWAY AND METHODS OF USE THEREOF
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Paragraph 0440, (2020/03/01)
The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.
Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
Ryabchuk, Pavel,Leischner, Thomas,Kreyenschulte, Carsten,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information, p. 18679 - 18685 (2020/09/02)
A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.
ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR
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Paragraph 0230; 0240; 0241; 0590; 0592; 0593, (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.
Self-Assembled Magnetic Gold Catalysts from Dual-Functional Boron Clusters
Qi, Bin,Wu, Chenchen,Li, Xin,Wang, Dan,Sun, Liang,Chen, Bo,Liu, Wenjing,Zhang, Haibo,Zhou, Xiaohai
, p. 2285 - 2290 (2018/05/15)
A new class of core–shell magnetic gold nanocomposites is prepared in a raspberry-like fashion by the controlled supramolecular host–guest assembly of γ-cyclodextrins (γ-CDs) and boron clusters. In this work, Cs2[closo-B12H12], a fundamental boron cluster, can play a dual role in the preparation of highly monodispersed Au nanoparticles and in the immobilization of Au nanoparticles on the γ-CDs@Fe3O4 surface as an effective anchor. This facile and spontaneous supramolecular strategy allows for the control of the size and composition of the highly stable gold composites. Furthermore, the obtained AuNPs@Fe3O4 composites exhibit an excellent catalytic activity and recyclability for the selective reduction of nitroaromatics to their corresponding aniline compounds, and the fastest reaction can be achieved within 20 s with a high conversion and selectivity at room temperature, which is better than that obtained previously in studies on metal nanoparticle composites as catalysts.
