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.
HETEROARYL COMPOUNDS COMPRISING NITROGEN AND USE THEREOF
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Paragraph 0062; 0063; 0064; 0065; 0094'; 0095; 0096; 0097, (2017/11/14)
The present invention relates to heteroaryl compounds comprising nitrogen and use thereof, and more specifically to compounds which exhibit a remarkable effect on inhibiting proliferation of cancer cells and metastasis and recurrence of cancer, a preparat
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.
A PROCESS FOR THE PREPARATION OF ALCAFTADINE
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Page/Page column 17; 18, (2014/06/23)
An improved process for preparation of Alcaftadine, its crystalline form or its pharmaceutically acceptable salts is disclosed alongwith a process for purification of Alcaftadine or its pharmaceutically acceptable salts.
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
Substituted heteroaromatic compounds: Effect on nicotine self-administration in rats
Cashman, John R.,Okolotowicz, Karl,Cerny, Matt,Johnson, Robert,Janowsky, Aaron,Azar, Marc R.
experimental part, p. 637 - 648 (2012/09/07)
Rationale: Certain compounds that nonselectively inhibit a prominent human nicotine-metabolizing enzyme (i.e., human cytochrome P-450 2A6, hCYP 2A6) showed inhibition of smoking in humans. However, a comprehensive examination of hCYP 2A6 inhibitors to dec
HEME-OXYGENASE INHIBITORS AND USE OF THE SAME IN THE TREATMENT OF CANCER AND DISEASES OF THE CENTRAL NERVOUS SYSTEM
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Page/Page column 70, (2009/01/24)
Disclosed are compounds of the general formula (1): compositions comprising an effective amount of said compounds either alone or in combination with other chemotherapeutic agents, and methods useful for treating or preventing cancer and for inhibiting tumour tissue growth. These compounds attenuate the oxidative damage associated with increased heme-oxygenase activity and can reduce cell proliferation in transformed cells. In addition, the described compounds and compositions are useful as neuroprotectants and for treating or preventing neurodegenerative disorders and other diseases of the central nervous system.
Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH
Clyne, Mairead A.,Aldabbagh, Fawaz
, p. 268 - 277 (2007/10/03)
Six-membered photochemical cyclisations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. The decrease in yield of cyclisation products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclisation was only successful under photochemical conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinoline with nitric/sulfuric acid occurred at the 2- and 8-positions. The Royal Society of Chemistry 2006.
Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)
Patel, Chirag H.,Dhanani, Sachin,Owen, Caroline P.,Ahmed, Sabbir
, p. 4752 - 4756 (2007/10/03)
We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17α-hydroxylase/17,20-lyase (P45017α), that is, 17α-hydroxylase (17α-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 μM against 17α-OHase and IC50 = 0.33 μM against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 μM against 17α-OHase and IC50 = 1.66 μM against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency.
Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols
Matsuoka, Yuki,Ishida, Yasuhiro,Sasaki, Daisuke,Saigo, Kazuhiko
, p. 8199 - 8206 (2007/10/03)
A highly versatile method for the preparation of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate.
