49823-14-5Relevant articles and documents
Novel phenethylimidazolium based ionic liquids: Design, microwave synthesis, in-silico, modeling and biological evaluation studies
Ali, Imran,Almutairi, Saud M.,Alqurashy, Bakheet A.,Alrefaei, Abdulwahed F.,Hammouti, Belkheir,Manoharadas, Salim,Messali, Mouslim,Sahu, Pramod K.,Titi, Abderrahim,Touzani, Rachid
, (2020/07/23)
An eco-friendly preparation method for the novel bioactive imidazolium ionic liquids halides (ILs) was developed under microwave-assisted conditions. Synthesized ILs were characterized by spectroscopic techniques. Selected ILs were investigated for their antimicrobial activity against highly resistant Gram-positive and Gram-negative bacterial strains. Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-iumchloride (4) showed high antimicrobial activity against the Staphylococcus aureus strain in the inhibition zone tests and displayed low MIC and MBC levels against almost all tested bacteria. Furthermore, the ILs were screened in vitro against human hepatocellular carcinoma (HepG-2), human breast adenocarcinoma (MCF-7), and human colon carcinoma (Caco-2) cell lines. The screening results showed excellent to moderate anticancer activity across the ILs. Among the synthesized ILs, Overall, 3-(2-chlorobenzyl)-1-phenethyl-1H-imidazol-3-ium chloride (4) and 1-phenethyl-3-(3-phenoxypropyl)-1H-imidazol-3-ium bromide (7) were found to exhibit the most promising ant proliferative effects and had the lowest IC50 values. The docking study suggested strong interaction of ILs with DNA with binding energy ranging from ?4.9 to ?4.1 kcal/mol. ILs 4 and 7 were most strongly bonded with ?4.9 and ?4.8 kcal/mol binding energy; confirming in vitro anticancer results.
Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors
R?hrig, Ute F.,Majjigapu, Somi Reddy,Chambon, Marc,Bron, Sylvian,Pilotte, Luc,Colau, Didier,Van Den Eynde, Beno?t J.,Turcatti, Gerardo,Vogel, Pierre,Zoete, Vincent,Michielin, Olivier
, p. 284 - 301 (2014/08/05)
Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.
Heme Oxygenase Inhibition by α-(1H-Imidazol-1-yl)-ω-phenylalkanes: Effect of Introduction of Heteroatoms in the Alkyl Linker
Vlahakis, Jason Z.,Lazar, Carmen,Roman, Gheorghe,Vukomanovic, Dragic,Nakatsu, Kanji,Szarek, Walter A.
experimental part, p. 897 - 902 (2012/07/30)
Several α-(1H-imidazol-1-yl)-ω-phenylalkanes were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). These compounds were found to be potent and selective for the stress-induced isozyme HO-1, showing mostly weak activity toward the cons
