82326-40-7Relevant academic research and scientific papers
One-pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies
Ersan, Ronak Haj,Yuksel, Ahmet,Ertan-Bolelli, Tugba,Dogen, Aylin,Burmaoglu, Serdar,Algul, Oztekin
, p. 374 - 383 (2020/09/21)
In an attempt to design a greener approach for the synthesis of a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various 1/2-carboxylic acid-substituted naphthalene derivatives to generate a series of naphthyl-substituted benzimidazole derivatives (11–19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco-friendly and swift reaction method for a synthetic approach to diverse benzimidazoles. Structures of the synthesized compounds were established on the basis of spectral data and they were screened for their antimicrobial activity. Compound 18 showed maximum potency against all Gram-positive and Gram-negative bacterial strains with a minimum inhibitory concentration (MIC) value in the range of 7.81–62.50 μg/ml. Only compound 17 was found to be the most active against all fungal strains with a MIC value of 15.62 μg/ml. In this study, we performed molecular docking experiments to understand the interactions between compounds 17 and 18 and E. coli topoisomerase I, and we compared the results obtained with that of 2-(3,4-dimethoxyphenyl)-5-[5-(4-methylpiperazin?1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazole (DMA). Compounds 17 and 18 demonstrated strong interactions with important active site residues, similar to DMA. As a result, the compounds obtained from this study can be used in designing new potent inhibitors of E. coli topoisomerase I.
Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators
Charton, Julie,Girault-Mizzi, Sophie,Debreu-Fontaine, Marie-Ange,Foufelle, Fabienne,Hainault, Isabelle,Bizot-Espiard, Jean-Guy,Caignard, Daniel-Henri,Sergheraert, Christian
, p. 4490 - 4518 (2007/10/03)
Design, synthesis and structure-activity relationships of benzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure-activity relationships are being described.
Studies in the Vilsmayer-Haack Reaction: Part XXVII-Attempted Synthesis of Acenaphthylene Derivatives-Formation of Benzimidazoisoquinolines
Padmanabhan, S.,Seshadri, S.
, p. 1111 - 1114 (2007/10/02)
The Vilsmayer reaction on benzimidazoles derived from arylacetic acids fails to give the acenaphthylene derivatives; instead the reaction leads to the synthesis of bezimidazoisoquinoline derivatives.
