- Meso -(2-Benzimidazolyl)-substituted BODIPYs: Synthesis, structures and spectroscopic properties
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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.
- Gao, Hu,Li, Chenhong,Shen, Zhen
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- 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
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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%.
- Liu, Shenggui,Pan, Rongkai,Su, Wenyi,Li, Guobi,Ni, Chunlin
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- A novel rhodamine-benzimidazole conjugate as a highly selective turn-on fluorescent probe for Fe3+
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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.
- Li, Junbo,Hu, Qihui,Yu, Xianglin,Zeng, Yang,Cao, Cancan,Liu, Xiwen,Guo, Jia,Pan, Zhiquan
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- Structure-based design of novel benzimidazole derivatives as PIN1 inhibitors
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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.
- Wang, Shuxiang,Guan, Lihong,Zang, Jie,Xing, Kun,Zhang, Jian,Liu, Dan,Zhao, Linxiang
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- 18 beta-glycyrrhetinic acid derivative and application thereof
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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.
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- Ruthenium complex as well as preparation method and application thereof
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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.
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Paragraph 0028-0031
(2018/04/01)
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- Benzimidazole - 2 - formaldehyde synthesis process
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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.
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Paragraph 0014-0016; 0017-0018; 0019-0020
(2018/04/01)
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- Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
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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.
- Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
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- With tyrosine kinase inhibitory activity of 2 - indolone derivatives and its preparation method and application
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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.
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- One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives
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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.
- Jiang, Zeng-Qiang,Miao, Da-Zhuang,Tong, Yao,Pan, Qiang,Li, Xiao-Tong,Hu, Ren-He,Han, Shi-Qing
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p. 1913 - 1921
(2015/06/30)
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- Solid phase synthesis of benzimidazole ketones and benzimidazole chalcones under solvent-free conditions
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Oxidation of 1-alkyl/aralkyl-2-(α-hydroxyalkyl/aryl)benzimidazoles 1 with KMnO4 on neutral alumina under solid phase conditions gives the corresponding ketones, 1-alkyl/aralkyl-2-acyl-benzimidazoles 2. Compound 2a (R2 = CH3) on condensation with aromatic aldehydes in the presence of solid NaOH under solvent-free conditions, yields the corresponding chalcones, 1-alkyl/aralkyl-2-benzimidazole aryl vinyl ketone 3.
- Dubey,Kumar, C. Ravi,Babu, Balaji
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p. 3128 - 3130
(2007/10/03)
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- Compounds of chromium(VI): The pyridine-chromic anhydride complex, benzimidazolinium dichromate, and three 2-alkyl-1H-benzimidazolinium dichromates
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Pyridine, when allowed to react with chromic anhydride under strictly anhydrous conditions, gives the known, very air-sensitive, crystalline 2:1 Lewis acid-base complex 1. The crystal structure has now been successfully determined. When benzimidazole and three 2-alkyl-1H-benzimidazoles were treated with chromium trioxide in aqueous acetic acid, crystalline dichromate salts (2-5) were readily formed. These salts consist of dichromate anions linked to the cations by hydrogen bonds of the type N-H...O. The chromium atoms have distorted tetrahedral environments, with the Cr-O distances being typical for dichromate anions. In the cases of the 2-methyl and 2-ethyl salts, the anions are disordered about a centre of inversion. The hydrogen bonding arrangements are discussed and the structures are compared with other oxygenated chromium(VI) species. The dichromate salts are useful selective oxidants for a range of primary and secondary alcohols; examples of these reactions are reported.
- Cameron, T. Stanley,Clyburne, Jason A.C.,Dubey, Pramod K.,Grossert, J. Stuart,Ramaiah,Ramanatham,Sereda, Sergei V.
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p. 612 - 619
(2007/10/03)
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- Benzimidazolium dichromates: Efficient reagents for selective oxidation of alcohols to carbonyl compounds
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Benzimidazolium dichromates have been used for the selective and efficient oxidation of simple alcohols to carbonyl compounds. 2-Methylbenzimidazolium dichromate has been used as a standard compound. It has been found to oxidize selectively, primary alcohols to aldehydes, without any over-oxidation, and secondary alcohols to ketones. Of the several solvents explored, acetic acid at RT has been found to be the best medium for oxidation.
- Ramaiah,Dubey,Ramanatham,Kumar, C. Ravi,Grossert
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p. 1765 - 1767
(2007/10/03)
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- Two-dimensional nitroxide-based molecular magnetic materials
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Manganese(II) complexes of imidazolyl-substituted chelating nitronylnitroxides are characterized by a stereoselective arrangement of the metal centers and the ligands to give a honeycomblike layer structure (shown on the right). The magnetic properties at high temperature indicate the presence of a ferrimagnetic structure within the layers. At low temperatures, ferromagnetic ordering is observed.
- Fegy, Karine,Luneau, Dominique,Ohm, Thorsten,Paulsen, Carley,Rey, Paul
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p. 1270 - 1273
(2007/10/03)
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- Certain aryl substituted imidazopyrazinones; a new class of GABA brain receptor ligands
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This invention encompasses compounds of formula I: STR1 or the pharmaceutically acceptable non-toxic salts thereof wherein: STR2 represents: STR3 where n is 0, 1, or 2; R 1 and R 2 are hydrogen or straight or branched chain alkyl groups;Y represents various organic and inorganic substituents;W represents an aromatic group substituted with various organic and inorganic substituents;A is CH or N;B is a substituted or unsubstituted carbon or N; andE is hydrogen or straight or branched alkyl groups.These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.
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- 6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof
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Antibacterial penicillins of the formula STR1 or a pharmaceutically acceptable salt thereof wherein R1 is a heterocyclic group and R is hydrogen, the residue of certian carboxy protecting groups or the residue of an ester group readily hydrolyzable in vivo having activity against resistant organisms.
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- Practicable Syntheses of 2-Hydroxymethyl-substituted Benzimidazoles and 2-Formylbenzimidazole
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N-Protection of benzimidazole by a diethoxymethyl group, as in , allows exclusive lithiation at the 2-position.This protected anion can be made to react with various electrophiles (e. g. ketones, aldehydes) to yield the corresponding 2-hydroxymethylbenzimidazoles (1).Facile deprotection occurs with acid.Two practicable syntheses of 2-formylbenzimidazole are also described and an indirect route to benzimidazole-2-alcohols is discussed.
- Ooi, Hong Chin,Suschitzky, Hans
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p. 2871 - 2876
(2007/10/02)
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- Oxidation of Methyl Group: Kinetics of Cerium(IV) Oxidation of 2-Methyl Benzthiazole, Benzoxazole and Benzimidazole in Acetic-Perchloric Acid Mixture
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Certic ion oxidation of 2-methyl benzthiazole, benzoxazole and benzimidazole has been examined at = 0.5M-2.5M following the disappearance of cerium titrimetrically.The rates are consistent with a mechanism involving the rapid formation of a complex which disproportionates to form the products.The rate increases with increase of and ionic strength indicating a positive salt effect.Evidence for complex formation is obtained from Michaelis Menten reciprocal plots.The activation parameters are compared.
- Singh, B. C.,Nayak, P.L.,Rout, M. K.,Padhi, N.P.
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p. 349 - 351
(2007/10/02)
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