3314-30-5Relevant articles and documents
Meso -(2-Benzimidazolyl)-substituted BODIPYs: Synthesis, structures and spectroscopic properties
Gao, Hu,Li, Chenhong,Shen, Zhen
, p. 230 - 237 (2020)
A series of meso-(2-benzimidazolyl)-substituted boron dipyrromethene (BODIPY) derivatives 3a-3c and 4 have been synthesized and characterized. The absorption and fluorescence bands of 3a are bathochromically shifted by 36 nm and 61 nm, respectively, compared with those of the meso-phenyl BODIPY in toluene. More importantly, the fluorescence quantum yields of these meso-(2-benzimidazolyl)-substituted BODIPYs (up to 0.45 in toluene) are much higher than those of the previously reported meso-heterocyclic BODIPYs. X-ray crystallographic analysis of the single crystal structure of 3a revealed that the dihedral angle of meso-benzimidazolyl ring and indacene plane (40.47) is smaller compared with that of the meso-tolyl substituted BODIPY (61.4). Replacement of the six-membered ring with a five-membered ring, as well as the absence of hydrogen at the imino-nitrogen, generated the reduced repulsion and the hydrogen bonding interaction. The increased planarity not only provided the substantial delocalization of π electrons and red shifted the absorption and emission bands but also enhanced the fluorescence quantum yield by reducing free rotation induced nonradiative deactivation pathway. Furthermore, 3,5-distyryl coupled BODIPY 4 exhibits a NIR fluorescence band at 712 nm with moderate quantum yield (φF > 0.3) in nonpolar and polar solvents, which indicate that meso-(2-benzimidazolyl) BODIPY acts as a good candidate for post modification toward NIR dyes for biological applications.
Synthesis of a ruthenium complex based on 2,6-bis[1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-yl]pyridine and catalytic oxidation of (1H-benzo[d]-imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehyde with H2O2
Liu, Shenggui,Pan, Rongkai,Su, Wenyi,Li, Guobi,Ni, Chunlin
, p. 88 - 92 (2017)
2,6-Bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine (bpbp), which has been synthesised by intramolecular thermocyclisation of N2,N6-bis[2-(pyridin-2-ylamino)phenyl]pyridine-2,6-dicarboxamide, reacts with sodium pyridine-2,6-dicarboxylate (pydic) and RuCl3 to give [Ru(bpbp)(pydic)] which can catalyse the oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehyde by H2O2. The optimal reaction conditions were: molar ratios of catalyst to substrate to H2O2 set at 1 : 1000 : 3000; reaction temperature 50 °C; reaction time 5 h. The yield of (1H-benzo[d]imidazol-2-yl) methanol was 70%.
A novel rhodamine-benzimidazole conjugate as a highly selective turn-on fluorescent probe for Fe3+
Li, Junbo,Hu, Qihui,Yu, Xianglin,Zeng, Yang,Cao, Cancan,Liu, Xiwen,Guo, Jia,Pan, Zhiquan
, p. 2005 - 2013 (2011)
In this manuscript, a novel probe RHBI based on the rhodamine-benzimidazole conjugate was designed and synthesized. RHBI showed an extreme selectivity for Fe3+ over other metal ions such as Pb2+, Ni2+, Co2+, Mn2+, Zn2+, Hg2+, Cd 2+, Ag+, Mg2+, Ca2+, Ba 2+, Na+ and K+ in acetonitrile. Upon the addition of 10 equiv. of Fe3+, a 1098-fold fluorescence intensity enhancement was observed at the maximum emission wavelength of 582 nm. Both the Job's plot and ESI-MS showed that RHBI coordinated with Fe3+ in a 1:1 stoichomitry and the calculated binding constant was 1. 01∈×∈104 M-1. The competition experiment for Fe3+ ions mixed with other metal ions exhibited no obvious change except Cu2+ that could induce a mild fluorescence quenching. Moreover, the fluorescence emission increased linearly with the Fe3+ concentration in the range of 6∈×∈10-6- 4∈×∈10-5 M and the detection limit was 1.5∈×∈10-8 M.
Structure-based design of novel benzimidazole derivatives as PIN1 inhibitors
Wang, Shuxiang,Guan, Lihong,Zang, Jie,Xing, Kun,Zhang, Jian,Liu, Dan,Zhao, Linxiang
, (2019/04/08)
Peptidyl-prolyl cis/trans isomerase Pin1 plays a key role in amplifying and translating multiple oncogenic signaling pathways during oncogenesis. The blockade of Pin1 provided a unique way of disrupting multiple oncogenic pathways and inducing apoptosis. Aiming to develop potent Pin1 inhibitors, a series of benzimidazole derivatives were designed and synthesized. Among the derivatives, compounds 6h and 13g showed the most potent Pin1 inhibitory activity with IC50 values of 0.64 and 0.37 μM, respectively. In vitro antiproliferative assay demonstrated that compounds 6d, 6g, 6h, 6n, 6o and 7c exhibited moderate antiproliferative activity against human prostate cancer PC-3 cells. Taken together, these unique benzimidazole derivatives exhibited great potential to be further explored as potent Pin1 inhibitors with improved potency.
Benzimidazole - 2 - formaldehyde synthesis process
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Paragraph 0014-0016; 0017-0018; 0019-0020, (2018/04/01)
The invention relates to a synthesizing process of benzimidazole-2-formaldehyde. The synthesizing process comprises the following steps: hydroxyapatite powder is taken as a catalyst, hot water with the temperature of 46 DEG C to 58 DEG C is taken as a solvent, o-phenylenediamine and glyoxylic acid are taken as raw materials for reaction, the molar ratio of the o-phenylenediamine and the glyoxylic acid is 1:(1-1.2), the reaction time is 2-10 h, the reaction temperature is 46 DEG C to 58 DEG C, after the reaction, filtrate is cooled to the temperature of 0 DEG C to 4 DGE C while the solution is hot, white crystals are precipitated, and crystals are obtained through filtration and dried, so that the benzimidazole-2-formaldehyde is obtained. According to the synthesizing process, the raw materials and the catalyst are easy to obtain, and the cost is low; 100 DEG C is not required in the operation steps, and the reaction condition of 46 DEG C to 58 DEG C is relatively mild; the target object of the benzimidazole-2-formaldehyde can be obtained by post-process through filtration, cooling and re-filtration, the operation is simple, and accordingly, the synthesizing process is suitable for industrial large-scale synthesis of the benzimidazole-2-formaldehyde.
18 beta-glycyrrhetinic acid derivative and application thereof
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, (2017/09/18)
The invention relates to the technical field of medicines, in particular to an 18 beta-glycyrrhetinic acid derivative with Pin1 inhibitory activity and pharmacologically-acceptable salt thereof, a preparation method of the derivative, a pharmaceutical composition taking the derivative as an active ingredient and application of the derivative to the preparation of a Pin1 inhibitor and the preparation of a drug for treating and/or preventing various cancers. The derivative shown in a general formula I or the pharmacologically-acceptable salt thereof has the following structure, wherein R, X, Y and n are stated in the claims and the descriptions.
Ruthenium complex as well as preparation method and application thereof
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Paragraph 0028-0031, (2018/04/01)
The invention relates to a ruthenium complex as well as a preparation method and application thereof. A structure of the ruthenium complex is shown in a formula (I), (II) or (III): the formulas (I), (II) and (III) are shown in the description. Hydrogen peroxide oxidizing 2-hydroxyalkyl benzimidazole can be catalyzed by the ruthenium complex provided by the invention at temperature of less than 80 DEG C so as to prepare 2-carbonyl benzimidazole; moreover, the catalytic activity is strong, the catalytic reaction yield is high, a condition is mild and the pollution is little.
Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
, (2016/12/03)
A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
With tyrosine kinase inhibitory activity of 2 - indolone derivatives and its preparation method and application
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, (2017/07/01)
The invention discloses a 2-indolone derivative with tyrosine kinase inhibition activity, geometric isomers and medicinal salts thereof, and a preparation method and an application of the above compounds. Tyrosine kinase inhibition activity evaluation confirms that the derivative is a compound with good tyrosine kinase activity, so the derivative has potential antitumor activity, and can be used to prepare tumor disease prevention and treatment medicines (antitumor medicines) as an active component. The derivative provides research and enforcement foundation for tumor treatment, and has a wide application prospect.
One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives
Jiang, Zeng-Qiang,Miao, Da-Zhuang,Tong, Yao,Pan, Qiang,Li, Xiao-Tong,Hu, Ren-He,Han, Shi-Qing
, p. 1913 - 1921 (2015/06/30)
A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.
