14085-43-9Relevant articles and documents
Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus
Dong, Jianghong,Chen, Shengwei,Li, Runfeng,Cui, Wei,Jiang, Haiming,Ling, Yixia,Yang, Zifeng,Hu, Wenhui
, p. 605 - 615 (2015/12/30)
We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 μM) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated.
Imidazole- and benzimidazole-based inhibitors of the kinase IspE: Targeting the substrate-binding site and the triphosphate-binding loop of the ATP site
Mombelli, Paolo,Le Chapelain, Camille,Munzinger, Noah,Joliat, Evelyne,Illarionov, Boris,Schweizer, W. Bernd,Hirsch, Anna K. H.,Fischer, Markus,Bacher, Adelbert,Diederich, Francois
, p. 1068 - 1079 (2013/03/28)
The enzymes of the mevalonate-independent biosynthetic pathway to isoprenoids are attractive targets for the development of new drug candidates, in particular against malaria and tuberculosis, because they are present in major human pathogens but not in humans. Herein, the structure-based design, synthesis, and biological evaluation of a series of inhibitors featuring a central imidazole or benzimidazole scaffold for the kinase IspE from E. coli, a model for the corresponding malarial enzyme, are described. Optimization of the binding preferences of the hydrophobic sub-pocket at the substrate-binding site allowed IC50 values in the lower micromolar range to be reached. Structure-activity relationship studies using a 1,2-disubstituted imidazole central core revealed that alicyclic moieties fit the sub-pocket better than acyclic aliphatic and aromatic residues. The phosphate-binding region in the ATP-binding site of IspE, a neutral glycine-rich loop, was addressed for the first time by an additional vector attached to the central core. Polar functional groups, such as trifluoromethyl or nitriles, were introduced to undergo orthogonal dipolar interactions with the amide groups in the loop. Alternatively, small hydrogen-bond-accepting heterocyclic residues, capable of binding to the convergent NH groups in the loop, were explored. The biological data showed slightly improved inhibitory potency in some cases and confirmed the challenges in addressing, with gain in binding affinity, the highly water-exposed sections of enzyme active sites, such as the glycine-rich loop of IspE. Inhibitors of the kinase E. coli IspE, an enzyme involved in the synthesis of isoprenoids and a model for IspE from P. falciparum, were developed. Decorated imidazole- and benzimidazole-based scaffolds address the cytidine-binding pocket, the hydrophobic sub-pocket, and the phosphate-binding region in the active site. In vitro activities in the micromolar IC 50-range were measured. Copyright
NITROGEN-CONTAINING ORGANIC COMPOUND, CHEMICALLY AMPLIFIED POSITIVE RESIST COMPOSITION, AND PATTERNING PROCESS
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, (2012/03/12)
An aralkylcarbamate of imidazole base is effective as the quencher. In a chemically amplified positive resist composition comprising the carbamate, deprotection reaction of carbamate takes place by reacting with the acid generated upon exposure to high-en
Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin
Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Nameni, Iman
experimental part, p. 2146 - 2148 (2011/04/24)
In the present work, dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], is reported. A wide variety of 2-imidazolines efficiently converted to their corresponding imidazoles by [Mn(TPP)Cl]/NaIO4 catalytic system at room temperature in 1:2, CH3CN/H2O mixture. The effect of reaction parameters such as kind of solvent and catalyst amount was also investigated.
Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl
Kargar, Hadi
experimental part, p. 863 - 866 (2011/06/25)
Rapid and efficient oxidation of 2-substituted imidazolines with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system efficiently converted 2-imidazolines to their corresponding imidazoles at room temperature in 2: 1, CH3CN/H2O mixture.
Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin
Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Naghipour, Mahmood
experimental part, p. 1463 - 1468 (2011/06/27)
In the present work, the dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride supported on polystyrene-bound imidazole, [Mn(TPP)Cl@PSI] is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by the [Mn(TPP)Cl@PSI]/NaIO4 catalytic system in a 1:2 CH3CN/H2O mixture under agitation with magnetic stirring. Ultrasonic irradiation enhanced the catalytic activity of this catalyst in the oxidation of 2-imidazolines and this led to shorter reaction times and higher product yields. This catalyst could be reused several times without significant loss of its catalytic activity.
An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo)benzene
Ishihara, Midori,Togo, Hideo
, p. 227 - 230 (2007/10/03)
2-Imidazolines were easily prepared in quite good yields from the reaction of aldehydes and ethylenediamine with molecular iodine in the presence of potassium carbonate. Moreover, 2-imidazolines obtained were smoothly oxidized to the corresponding imidazoles in good yields using (diacetoxyiodo)benzene at room temperature. Georg Thieme Verlag Stuttgart.
Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10
Mohammadpoor-Baltork, Iraj,Abdollahi-Alibeik, Mohammad
, p. 110 - 114 (2007/10/03)
Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO4) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.
Novel, mild and chemoselective dehydrogenation of 2-imidazolines with trichloroisocyanuric acid
Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali,Abdollahi-Alibeik, Mohammad
, p. 2803 - 2805 (2007/10/03)
A rapid, mild and high-yielding method for dehydrogenation of a variety of structurally diverse 2-imidazolines to imidazoles jusing trichloroisocyanuric acid (TCCA) in the presence of DBU is reported. Chemoselective oxidation of 2-imidazolines can be achieved in the presence of sulfide and alcohol. The mild conditions of this procedure and the absence of any transition metal make this reaction suitable for safe laboratory use.
Alumina supported potassium permanganate: An efficient reagent for chemoselective dehydrogenation of 2-imidazolines under mild conditions
Abdollahi-Alibeik, Mohammad,Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali
, p. 6079 - 6082 (2007/10/03)
An efficient method for the oxidation of 2-imidazolines to their corresponding imidazoles using KMnO4/Al2O3 under very mild reaction conditions is reported. Selective oxidation of 2-alkylimidazolines was also performed in the presence of 2-arylimidazolines and other functional groups such as sulfide, ether, aldehyde, acetal and THP ether. Potassium permanganate supported on alumina was found to be an efficient reagent system for dehydrogenation of 2-imidazolines to imidazoles under mild conditions at room temperature. Selective oxidation of 2-alkylimidazolines in the presence of 2-arylimidazolines was achieved using this reagent system. 2-Imidazolines were also selectively converted to their corresponding imidazoles in the presence of other oxidizable functional groups such as sulfide, ether, aldehyde, acetal and THP ether. The oxidation procedure described here is easy to carry out and does not require strict reaction conditions.
