119-75-5Relevant articles and documents
A new series of N-substituted tetraphenylethene-based benzimidazoles: Aggregation-induced emission, fast-reversible mechanochromism and blue electroluminescence
Zhang, Tengfei,Zhang, Ran,Zhao, Yun,Ni, Zhonghai
, p. 276 - 285 (2018)
Four new N-substituted tetraphenylethene-based benzimidazoles N-R-2-(4-(1,2,2-triphenylvinyl)phenyl)-1H-benzo[d]imidazoles (R = phenyl (3a), R = 4-(tert-butyl)phenyl (3b), R = n-butyl (3c), R = n-hexyl (3d)) were synthesized conveniently by cyclization reaction of 4-tetraphenylenthenealdehyde with N-substituted ortho-nitroaniline. The four compounds exhibit typical aggregation-induced emission (AIE) property with relatively high solid state absolute fluorescence quantum yields (38.1–65.7%) and fast-recoverable mechanochromism property with solid-state fluorescence change between blue and yellow-green. They are thermally stable with decomposition temperatures above 319 °C. Both of multilayer electroluminescence devices fabricated with compounds 3b and 3c as emitters are blue emission. The turn-on voltage of device based on compound 3b is 3.3 V with maximum luminance and current efficiency of 2470 cd/m2 and 1.48 cd/A, respectively.
11-(Tetrahydro-3 and 4-pyridinyl)dibenzo[b,e][1,4]diazepines undergo novel rearrangements on treatment with concentrated HBr
Cairns, James,Clarkson, Thomas R.,Hamersma, Johan A.M.,Rae, Duncan R.
, p. 1583 - 1585 (2002)
11-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine on heating in conc. HBr afforded trans-5-(2-aminophenyl)-1,3,4,4a,5,10a-hexahydro-2-methylbenzo[b][1,6] naphthyridin-10(2H)-one in one step. The isomer 11-(1,2,5,6-tetrahydro-1-methyl-4-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine underwent a novel rearrangement resulting in the pentacycle, 4-amino-5,13-diaza-13-methyl-bicyclo[3.3.1]nonan[6,7,8-k,l]acridine.
Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand
Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
, p. 8107 - 8109 (2005)
We have developed a general, efficient, and inexpensive catalyst system for arylation of amines by using 10 mol % of CuI as the copper source, 20 mol % of diphenyl pyrrolidine-2-phosphonate (DPP) as the ligand, K3PO 4 as the base, and DMF containing 2% water (v/v) as the solvent.
Solution-processed efficient deep-blue fluorescent organic light-emitting diodes based on novel 9,10-diphenyl-anthracene derivatives
Zhang, Zhaohang,Jiang, Wei,Ban, Xinxin,Yang, Min,Ye, Shanghui,Huang, Bin,Sun, Yueming
, p. 29708 - 29717 (2015)
A series of 9,10-diphenyl-anthracene derivatives bearing either benzimidazole or carbazole moieties as substituents were synthesized and characterized as blue emitters for organic light-emitting diodes (OLEDs). Their optical, electrochemical and thermal properties have been investigated, and their molecular structure-property relationships were evaluated. These compounds both exhibited a high glass-transition temperature (Tg ≥ 195 °C) and a high decomposition temperature (Td ≥ 494 °C). The solution processed non-doped device using CAC as a fluorescence emitter showed a maximum luminance efficiency of 1.63 cd A-1, a maximum power efficiency of 0.77 lm W-1 and a maximum external quantum efficiency of 1.53%. By introducing 1,3-bis[4-tert-butylphenyl-1,3,4-oxadiazolyl] phenylene (OXD-7):polyvinylcarbazole (PVK) as host in the emitting layer, the doped deep-blue emitting device of CAC exhibited a turn-on voltage of 4.75 V, a maximum luminance efficiency of 3.03 cd A-1, a maximum power efficiency of 1.64 lm W-1 and a maximum external quantum efficiency of 2.81%. Our results demonstrate a promising approach to well-designed materials for use in deep-blue fluorescence OLED applications. This journal is
Synthesis, photophysics, and reverse saturable absorption of bipyridyl platinum(II) bis(acetylide) complexes bearing aromatic electron-withdrawing substituents on the acetylide ligands
Liu, Xu-Guang,Sun, Wenfang
, p. 10318 - 10325 (2014)
Three platinum(II) bipyridyl bis((7-R-fluoren-2-yl)acetylide) complexes (R = benzoyl (Pt-1), 2-(N-phenylbenzimidazoly) (Pt-2), or 2-(3-phenylquinoxalinyl) (Pt-3)) are synthesized and characterized. Their photophysical properties and reverse saturable absorption are systematically investigated via UV-vis absorption, emission, transient absorption, and nonlinear transmission spectroscopy/technique. All three complexes possess ligand-centered 1π,π transitions below 400 nm, and a broad, featureless 1MLCT/1LLCT absorption band in the region of 400-550 nm in CH2Cl2 solutions. They are emissive in a variety of fluid solutions at room temperature and at 77 K glassy matrix. On the basis of the emission lifetime, solvatochromic effect, and thermally induced Stokes shift, the emitting states are tentatively ascribed to 3π,π/3MLCT/3LLCT states for Pt-1, and predominantly 3MLCT/3LLCT states for Pt-2 and Pt-3 in polar solvents like CH3CN. Pt-1-Pt-3 also exhibit broad triplet excited-state absorption, i.e., 425-800 nm for Pt-1 and Pt-3, and 425-725 nm for Pt-2, from the same excited states that emit. Strong reverse saturable absorption (RSA) occurs at 532 nm for ns laser pulses from all of the complexes due to the stronger triplet excited-state absorption at this wavelength, suggesting that the π-conjugated aromatic electron-withdrawing substituents at the fluorenylacetylide ligands enhance the RSA of the Pt(II) diimine bis(acetylide) complexes.
A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa
Mortzfeld, Frederik B.,Pietruszka, J?rg,Baxendale, Ian R.
, p. 5424 - 5433 (2019)
The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product have been facilitated by the use of flow chemistry techniques and immobilised reagents. Using these procedures gram quantities of pyocyanin were easily prepared in high yield and purity.
N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis
Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec
, (2021)
We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.
Design, synthesis, and structure-activity relationships of novel imidazo[4,5-c]pyridine derivatives as potent non-nucleoside inhibitors of hepatitis C virus NS5B
Liu, Moyi,Xu, Qiaoling,Guo, Su,Zuo, Ruixi,Hong, Yue,Luo, Yong,Li, Yingxiu,Gong, Ping,Liu, Yajing
, p. 2621 - 2631 (2018)
The hepatitis C virus (HCV) NS5B polymerase is an attractive target for the development of novel and selective inhibitors of HCV replication. In this paper, the design, synthesis, and preliminary SAR studies of novel inhibitors of HCV NS5B polymerase based on the structure of tegobuvir have been described. The efforts to optimize the antiviral potency and reduce the treatment side effects with respect to genotype 1b resulted in the discovery of compound 3, which exhibited an EC50 of 1.163 nM and a CC50 >200 nM in a cell-based HCV replicon system assay. Additionally, testing for inhibition of the hERG channel showed a marked improvement over tegobuvir and the pharmacokinetic properties of compound 3 indicated that it was worthy of further investigation as a non-nucleoside inhibitor of HCV NS5B polymerase.
Novel 4-phenoxy pyridine derivative and application thereof
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Paragraph 0049; 0063-0065, (2021/06/02)
The invention relates to a novel 4-phenoxy pyridine derivative and application thereof. The 4-phenoxy pyridine derivative has a structure as shown in a general formula (I), and the pharmacological activity test result of the novel 4-phenoxy pyridine derivative shows that the 4-phenoxy pyridine derivative has a remarkable inhibition effect on human gastric cancer cells MKN45, human lung cancer cells A549, human lung cancer cells H460 and human colon cancer cells HT-29; and meanwhile, the invention relates to a strong c-Met kinase inhibition effect of the compounds, and also relates to application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase, and application of the compounds and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase. particularly relates to application in preparation of medicines for treating and/or preventing cancers.
Design, synthesis, and biological evaluation of benzo[d]imidazole-2-carboxamides as new anti-TB agents
Dhameliya, Tejas M.,Patel, Kshitij I.,Tiwari, Rishu,Vagolu, Siva Krishna,Panda, Dulal,Sriram, Dharmarajan,Chakraborti, Asit K.
, (2020/12/29)
Tuberculosis is the leading cause of death globally among infectious diseases. Due to the development of resistance of Mycobacterium tuberculosis to currently used anti-TB medicines and the TB-HIV synergism the urgent need to develop novel anti-mycobacterial agents has been realized. The drug-to-target path has been the successful strategy for new anti-TB drug development. All the six drug candidates that have shown promise during the clinical trials and some of these being approved for treatment against MDR TB are the results of phenotype screening of small molecule compound libraries. In search of compounds belonging to novel pharmacophoric class that could be subjected to whole cell assay to generate new anti-TB leads the benzo[d]imidazole-2-carboxamide moiety has been designed as a novel anti-TB scaffold. The design was based on the identification of the benzimidazole ring as a prominent substructure of the FDA approved drugs, the structural analysis of reported anti-TB benzimidazoles, and the presence of the C-2 carboxamido functionality in novel bioisoteric anti-TB benzothiazoles. Twenty seven final compounds have been prepared via NH4Cl-catalyzed amidation of ethyl benzo[d]imidazole-2-carboxylates, as the required intermediates, obtained through a green “all water” one-pot synthetic route following a tandem N-arylation-reduction-cyclocondensation procedure. All of the synthesised target compounds were assessed for anti-TB potential using H37Rv ATCC27294 strain. Thirteen compounds were found with better MIC (0.78–6.25 μg/mL) than the standard drugs and being non-cytotoxic nature ( 60) and a few others e.g., 8a, 8f, 8k and 8o are the next best anti-TB hits (MIC: 1.56 μg/mL). The determination and analysis of various physiochemical parameters revealed favorable druglike properties of the active compounds. The compounds 8a-l and 8o, with MIC values of ≤ 6.25 μg/mL, have high LipE values (10.66–11.77) that are higher than that of the suggested value of > 6 derived from empirical evidence for quality drug candidates and highlight their therapeutic potential. The highest LipE value of 11.77 of the best active compound 8e with the MIC of 0.78 μg/mL indicates its better absorption and clearance as a probable clinical candidate for anti-TB drug discovery. These findings highlight the discovery of benzimidazole-2-carboxamides for further development as new anti-TB agents.
