4887-85-8Relevant academic research and scientific papers
Functionalized Dioxonaphthoimidazoliums: A Redox Cycling Chemotype with Potent Bactericidal Activities against Mycobacterium tuberculosis
Cook, Gregory M.,Dick, Thomas,Fridianto, Kevin T.,Go, Mei-Lin,Hards, Kiel,Lam, Yulin,Li, Ming,Negatu, Dereje A.
supporting information, p. 15991 - 16007 (2021/11/16)
Disruption of redox homeostasis in mycobacteria causes irreversible stress induction and cell death. Here, we report the dioxonaphthoimidazolium scaffold as a novel redox cycling antituberculosis chemotype with potent bactericidal activity against growing and nutrient-starved phenotypically drug-resistant nongrowing bacteria. Maximal potency was dependent on the activation of the redox cycling quinone by the positively charged scaffold and accessibility to the mycobacterial cell membrane as directed by the lipophilicity and conformational characteristics of the N-substituted side chains. Evidence from microbiological, biochemical, and genetic investigations implicates a redox-driven mode of action that is reliant on the reduction of the quinone by type II NADH dehydrogenase (NDH2) for the generation of bactericidal levels of the reactive oxygen species (ROS). The bactericidal profile of a potent water-soluble analogue 32 revealed good activity against nutrient-starved organisms in the Loebel model of dormancy, low spontaneous resistance mutation frequency, and synergy with isoniazid in the checkerboard assay.
An efficient strategy for N-alkylation of benzimidazoles/imidazoles in SDS-aqueous basic medium and N-alkylation induced ring opening of benzimidazoles
Chakraborty, Ankita,Debnath, Sudipto,Ghosh, Tanmoy,Maiti, Dilip K.,Majumdar, Swapan
, p. 5932 - 5941 (2018/09/18)
A sustainable route for the N-1 alkylation of imidazole and benzimidazole derivatives has been developed under volatile organic solvent free condition in alkaline water-SDS system. Incorporation of SDS in the reaction medium enhances the reaction rate by suppressing the solubility issue that arises for different substrates. This method provides high yield of the alkylated product in a shorter reaction time. For reactive alkyl halides reaction proceeds at ambient temperature whereas in the cases of less reactive alkyl halides require 55–60 °C to complete alkylation process. N-alkylation induced ring opening of the heterocyclic ring in benzimidazole derivatives to multifunctional aromatic compounds were noticed at 60 °C when more than two equivalents of alkyl halide was used.
Ligand-free copper-catalyzed synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles
Saha, Prasenjit,Ramana, Tamminana,Purkait, Nibadita,Ali, Md. Ashif,Paul, Rajesh,Punniyamurthy, Tharmalingam
supporting information; experimental part, p. 8719 - 8725 (2010/02/28)
(Chemical Equation Presented) The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramolecular cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. The procedure is experimentally simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity. 2009 American Chemical Society.
Quaternary ammonium salts used as phase transfer catalyst
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, (2008/06/13)
Novel quaternary ammonium salts of general formula (I) STR1 wherein: R is a saturated or unsaturated, linear or branched alkyl radical of C1 to C8. R' is a saturated or unsaturated, linear or branched alkyl radical of C1 to C12, or a benzyl radical. n is a number equal to 2 or 3. Xθ is a halogenide anion, such as Clθ, Brθ, Iθ, are used as phase transfer catalysts, in heterogeneous ionic reactions wherein the reagents are in different phase and have different polarity.
