- [Re(η6-C6H5-benzimidazole)2]+ and Derivatives as Dye Mimics; Synthesis, UV Absorption Studies and DFT Calculations
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Functionalizations of highly oxidation and hydrolysis stable mono-cationic rhenium bis-arene complexes [Re(η6-C6H6)2]+ are of great interest. We directly built up structural features of the well-known Hoechst Dye on the coordinated arenes as a model for prospective DNA minor groove binding studies. Extensions of the aromatic bis-arene unit with functionalized and derivatized benzimidazole moieties resulted in a deep orange colour of the complexes, showing UV/Vis absorption spectra with multiple transition maxima. These have been assigned with support of DFT calculations to gain information about their charge transfer natures. The different transitions of the complexes, which are either intra-ligand, ligand-to-ligand or metal-to-ligand charge transitions, were additionally compared and discussed with the spectra of the corresponding free ligands.
- Gotzmann, Carla,Blacque, Olivier,Fox, Thomas,Alberto, Roger
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Read Online
- Structure-Guided Synthesis and Evaluation of Small-Molecule Inhibitors Targeting Protein–Protein Interactions of BRCA1 tBRCT Domain
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The tandem BRCT domains (tBRCT) of BRCA1 engage phosphoserine-containing motifs in target proteins to propagate intracellular signals initiated by DNA damage, thereby controlling cell cycle arrest and DNA repair. Recently, we identified Bractoppin, the fi
- Kurdekar, Vadiraj,Giridharan, Saranya,Subbarao, Jasti,Nijaguna, Mamatha B.,Periasamy, Jayaprakash,Boggaram, Sanjana,Shivange, Amol V.,Sadasivam, Gayathri,Padigaru, Muralidhara,Potluri, Vijay,Venkitaraman, Ashok R.,Bharatham, Kavitha
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p. 1620 - 1632
(2019/11/05)
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- PIPERAZINE DERIVATIVES AS MAGL INHIBITORS
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The invention provides new heterocyclic compounds having general Formula (I), or a pharmaceutically acceptable salt thereof, wherein R1, R2, X, Y1 and Y2 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.
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- Targeting Phosphopeptide Recognition by the Human BRCA1 Tandem BRCT Domain to Interrupt BRCA1-Dependent Signaling
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Intracellular signals triggered by DNA breakage flow through proteins containing BRCT (BRCA1 C-terminal) domains. This family, comprising 23 conserved phosphopeptide-binding modules in man, is inaccessible to small-molecule chemical inhibitors. Here, we develop Bractoppin, a drug-like inhibitor of phosphopeptide recognition by the human BRCA1 tandem (t)BRCT domain, which selectively inhibits substrate binding with nanomolar potency in vitro. Structure-activity exploration suggests that Bractoppin engages BRCA1 tBRCT residues recognizing pSer in the consensus motif, pSer-Pro-Thr-Phe, plus an abutting hydrophobic pocket that is distinct in structurally related BRCT domains, conferring selectivity. In cells, Bractoppin inhibits substrate recognition detected by F?rster resonance energy transfer, and diminishes BRCA1 recruitment to DNA breaks, in turn suppressing damage-induced G2 arrest and assembly of the recombinase, RAD51. But damage-induced MDC1 recruitment, single-stranded DNA (ssDNA) generation, and TOPBP1 recruitment remain unaffected. Thus, an inhibitor of phosphopeptide recognition selectively interrupts BRCA1 tBRCT-dependent signals evoked by DNA damage. Periasamy et al. report the development of Bractoppin, a drug-like inhibitor of phosphopeptide recognition by the BRCA1 tBRCT domain, opening avenues to block intracellular signaling via a family of related targets.
- Periasamy, Jayaprakash,Kurdekar, Vadiraj,Jasti, Subbarao,Nijaguna, Mamatha B.,Boggaram, Sanjana,Hurakadli, Manjunath A.,Raina, Dhruv,Kurup, Lokavya Meenakshi,Chintha, Chetan,Manjunath, Kavyashree,Goyal, Aneesh,Sadasivam, Gayathri,Bharatham, Kavitha,Padigaru, Muralidhara,Potluri, Vijay,Venkitaraman, Ashok R.
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p. 677 - 12,690
(2018/06/21)
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- BENZIMIDAZOL DERIVATIVES FOR TREATING FILOVIRUS INFECTION
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The present invention relates to compounds comprising a benzimidazole scaffold, and the use of such compounds for the treatment of viral diseases. The invention also relates to pharmaceutical compositions comprising said compounds as an active ingredient. In particular the compounds of the invention comprising a benzimidazole scaffold are used for the treatment of filoviruses or retroviruses, and preferably for the treatment of Ebola virus or HIV virus.
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Page/Page column 17; 29; 30
(2018/04/13)
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- Chromium(III)-salen complex nanoparticles on AlPO4: as an efficient heterogeneous and reusable nanocatalyst for mild synthesis of highly functionalized piperidines, 2-arylbenzimidazoles, and 2-arylbenzothiazoles
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Abstract: A simple, convenient, and highly efficient multicomponent one-pot synthesis of highly functionalized piperidines has been developed via tandem reactions of β-keto esters, aromatic aldehydes, and various amines in ethanol at room temperature using catalytic amount (10?mol%) of a chromium(III)-salen complex nanoparticles supported on AlPO4. The heterogeneous catalyst exhibited excellent activity and reusability (up to 8 times) in the synthesis of highly functionalized piperidines. Also, synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles have been efficiently developed under mild condition from o-phenylenediamines or 2-aminothiophenol with aryl aldehydes via one-step process using catalytic amount (2.0?mol%) of nanocatalyst in air atmosphere as a green oxidant. The heterogeneous catalyst was characterized by scanning electron microscopy, atomic force microscopy, inductively coupled plasma spectrometry, thermogravimetry for analysis of nitrogen adsorption, and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].
- Sharghi, Hashem,Aberi, Mahdi,Doroodmand, Mohammad Mahdi,Shiri, Pezhman
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p. 1557 - 1573
(2017/06/06)
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- FUSED TRIAZOLE DERIVATIVES AS PHOSPHODIESTERASE 10A INHIBITORS
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Compounds of the general formula (I), wherein one of X1 and X2 represents N, and the other one of X1 and X2 represents -C(CH3), A represents unsubstituted or substituted 5-, 6-or 10-membered aryl or h
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- Synthetic Method of Benzimidazole via Aerobic Oxidation
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The present invention relates to a method which naturally synthesizes benzimidazole by reacting aryl diamine and aldehyde through using aerobic oxidative cyclization which uses water or alkali metal halide as a catalyst, and oxygen or oxygen in the air as an oxidizing agent, under DMF or an alcohol solvent.
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Paragraph 0104; 0110; 0194; 0195
(2016/11/14)
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- Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles
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A simple, convenient, and environmentally benign protocol for the synthesis of benzimidazoles from ortho-phenylenediamines and aldehydes via aerobic oxidation was developed in wet organic solvents. Notably, water significantly accelerated this transformation, which allowed us to achieve this important transformation without the assistance of any metal catalysts and other co-oxidants. Mechanistic studies suggested that water acts as the nucleophilic catalyst for this transformation by the conversion of disfavored 5-endo-trig cyclization of imines to favored 5-exo-tet cyclization via tetrahedral intermediates and the subsequent aerobic oxidation of the resulting benzimidazolines affords benzimidazoles.
- Lee, Ye-Sol,Cho, Yeon-Ho,Lee, Seungjae,Bin, Jong-Kwan,Yang, Joonghwan,Chae, Geesung,Cheon, Cheol-Hong
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supporting information
p. 532 - 538
(2015/02/05)
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- Synthesis and biological evaluation of novel benzimidazole derivatives bearing a heterocyclic ring at 4/5 position
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A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 (IC50 = 1.08 μg/mL, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.
- Wubulikasimu, Reyila,Yang, Yanbing,Xue, Fei,Luo, Xianjin,Shao, Dongping,Li, Yuhuan,Gao, Rongmei,Ye, Weidong
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p. 2297 - 2304
(2013/09/24)
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- One-pot synthesis of 2-arylbenzimidazole, 2-arylbenzothiazole and 2-arylbenzoxazole derivatives using vanadium(IV)-salen complex as homogeneous catalyst and vanadium(IV)-salen complex nanoparticles immobilized onto silica as a heterogeneous nanocatalyst
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The efficient synthesis of 2-arylbenzimidazole, 2-arylbenzothiazole and 2-arylbenzoxazole derivatives is described by condensation of aryl aldehydes and o-phenylenediamines, 2-aminothiophenol and 2-aminophenol in a single pot using a catalytic amount of vanadium(IV)-salen complex or vanadium-salen nanoparticles supported on silica (5.0 mol%) in excellent isolated yields. The immobilized catalyst was characterized by powder X-ray diffraction, scanning electron microscopy, atomic force microscopy, transmission electron microscopy, inductively coupled plasma analysis, thermogravimetric instrument for analysis of nitrogen adsorption and FT-IR spectroscopy.
- Sharghi, Hashem,Aberi, Mahdi,Doroodmand, Mohammad Mahdi
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experimental part
p. 189 - 204
(2012/08/27)
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- Aqueous 1M glucose solution as a novel and fully green reaction medium and catalyst for the oxidant-free synthesis of 2-arylbenzimidazoles
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The reaction of various o-phenylenediamines and substituted benzaldehydes was carried out in 1M glucose solution as reaction medium and catalyst under one-pot oxidantfree conditions. The desired products were obtained at 60 °C with good to excellent yields, and the reaction was performed chemoselectively without formation of 1,2-disubstituted benzimidazoles. No need for any extra oxidant, simple workup, and use of carbohydrates as fully green promoters are some advantages of the present work.
- Rostamizadeh, Shahnaz,Aryan, Reza,Ghaieni, Hamid Reza
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experimental part
p. 1794 - 1804
(2011/06/24)
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- Simple, efficient, and applicable route for synthesis of 2-Aryl(Heteroaryl)-benzimidazoles at room temperature using copper nanoparticles on activated carbon as a reusable heterogeneous catalyst
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A series of 2-(hetero)arylbenzimidazoles were synthesized by the catalytic condensation of (hetero)aryl aldehydes with 1,2-phenylenediamine derivatives at room temperature in the presence of air as the oxidant. Copper nanoparticles on charcoal was employed as an efficient and mild catalyst for this methodology. Graphical Abstract: [Figure not available: see fulltext.]
- Sharghi, Hashem,Khalifeh, Reza,Mansouri, Seyed Gholamhossein,Aberi, Mahdi,Eskandari, Mohammad Mehdi
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scheme or table
p. 1845 - 1850
(2012/02/14)
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- Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives
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Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.
- Cong, Chao,Wang, Haiyang,Hu, Yue,Liu, Chen,Ma, Siti,Li, Xin,Cao, Jichao,Ma, Shutao
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supporting information; experimental part
p. 3105 - 3111
(2011/07/08)
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- Novel clarithromycin analogs with C-4′′ 2-arylbenzimidazolyl bishydrazide side chain: Synthesis and antibacterial evaluation
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A series of novel 4′′-O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4′′-O-2- arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4′′ bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.
- Qi, Yunkun,Ma, Ruixin,Li, Xin,Hu, Yue,Ma, Siti,Cong, Chao,Ma, Xiaodong,Cui, Wenping,Ma, Shutao
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p. 966 - 971
(2012/07/01)
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- New one-pot procedure for the synthesis of 2-substituted benzimidazoles
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A highly selective synthesis of 2-substituted benzimidazole derivatives from the reaction of o-phenylendiamine derivatives and aromatic aldehydes in the presence of an organic salt, NH4OAc, in absolute ethanol is presented. The products were obtained by evaporating the solvent followed by a simple recrystallization with excellent yields. Copyright Taylor & Francis Group, LLC.
- Sharghi, Hashem,Asemani, Omid,Khalifeh, Reza
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p. 1128 - 1136
(2008/09/18)
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- Reusable cobalt(III)-salen complex supported on activated carbon as an efficient heterogeneous catalyst for synthesis of 2-arylbenzimidazole derivatives
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Various 2-arylbenzimidazoles were synthesized from phenylenediamines and aromatic aldehydes via a one-step process in the presence of a catalytic amount of a cobalt-salen complex supported on activated carbon [CoxO-Co(salen) 11] at room temperature. The salient features of this method include mild conditions, short reaction times, high yields, easy purification, recyclable catalyst, large-scale synthesis and simple procedure. The reactions were performed in ethanol and the catalyst could be reused for several cycles without a decrease in activity. The heterogeneous catalyst was characterized by powder X-ray diffraction (XRD), scanning electron microscopy (SEM), atomic forced microscopy (AFM), thermogravimetric (TG) methods for analysis of nitrogen adsorption and FT-IR spectroscopy. Leaching experiments showed that the catalyst is most strongly anchored to the activated support after 10 cycles of reuse.
- Sharghi, Hashem,Aberi, Mahdi,Doroodmand, Mohammad Mahdi
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supporting information; experimental part
p. 2380 - 2390
(2009/10/18)
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- Copper-catalyzed one-pot synthesis of benzimidazole derivatives
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A simple, efficient, and environmentally benign method has been developed for the synthesis of 2-substituted benzimidazoles through a one-pot reaction of phenylenediamines with ary1 aldehydes in excellent isolated yields under mild conditions using Cu(II) complex as the selective, recyclable, and heterogeneous catalyst at ambient temperature. The Cu(II) complex as a heterogeneous catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for eight successive runs. No metal-complex leaching was observed after the consecutive catalytic reactions. The salient features of this method include mild conditions, high yields, simple procedure, and good recovery and reusability of the heterogeneous catalyst.
- Sharghi, Hashem,Hosseini-Sarvari, Mona,Moeini, Fatemeh
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experimental part
p. 1044 - 1051
(2009/02/08)
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- SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLE-5(6)-CARBOXAMIDES AND EVALUATION OF THEIR ANTIMICROBIAL ACTIVITY
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A series of 14,N'-(N,N-dialkylaminoethyl)-benzimidazole-5(6) or 5-carboxamides (1-14), having several substituents on the azole and benzene nuclei, were prepared and evalueted in vitro for antimicrobial activity.The precursor bezimidazolecarboxylic acids (15-27) were prepared via oxidative condensation of diaminobenzoic acids and several aldehydes with cupric ion.Compounds 11-14 were prepared by selective regioisomer synthesis.All carboxamides were prepared from the corresponding acids and N,N-dialkylethylenediamine.Antibacterial and antifungal activities were determined as MICs values.Of the synthesized compounds 1-10, 6 and 10 were found to be most favourable.In order to clarify the effect of the substituents at N1 on antimicrobial activity, 12 was prepared by p-chlorobenzyl substitution of compound 6, and increased activity was shown.Compounds 13 and 14, which were prepared by replacement with more bulky alkyl groups on the tert-N atom than 12, gave the best results.
- Goeker, Hakan,Tebrizli, Emin,Abbasoglu, Ufuk
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