37910-79-5Relevant academic research and scientific papers
One pot synthesis of α-N-heteroaryl ketone derivatives from aryl ketones using aqueous NaICl2
Ghodse, Shrikant M.,Hatvate, Navnath T.,Telvekar, Vikas N.
supporting information, (2021/12/08)
A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.
Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer
Sun, Bin,Hoshino, Juma,Jermihov, Katie,Marler, Laura,Pezzuto, John M.,Mesecar, Andrew D.,Cushman, Mark
experimental part, p. 5352 - 5366 (2010/09/05)
A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 μM) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 μM. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC 50 1.7 μM and 0.27 μM, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer.
Heme oxygenase inhibition by 1-Aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1- yl)ethanones and their derivatives
Roman, Gheorghe,Vlahakis, Jason Z.,Vukomanovic, Dragic,Nakatsu, Kanji,Szarek, Walter A.
experimental part, p. 1541 - 1555 (2011/11/29)
Previous studies by our research group have been concerned with the design of selective inhibitors of heme oxygenases (HO-1 and HO-2). The majority of these were based on a four-carbon linkage of an azole, usually an imidazole, and an aromatic moiety. In the present study, we designed and synthesized a series of inhibition candidates containing a shorter linkage between these groups, specifically, a series of 1-aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1-yl) ethanones and their derivatives. As regards HO-1 inhibition, the aromatic moieties yielding best results were found to be halogen-substituted residues such as 3-bromophenyl, 4-bromophenyl, and 3,4-dichlorophenyl, or hydrocarbon residues such as 2-naphthyl, 4-biphenyl, 4-benzylphenyl, and 4-(2-phenethyl)phenyl. Among the imidazole-ketones, five (36-39, and 44) were found to be very potent (IC5050 in favor of HO-1. In the case of the azole-dioxolanes, two of them (80 and 85), each possessing a 2-naphthyl moiety, were found to be particularly potent and selective HO-1 inhibitors. Three non-carbonyl analogues (87, 89, and 91) of 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethanone were found to be good inhibitors of HO-1. For the first time in our studies, two azole-based inhibitors (37 and 39) were found to exhibit a modest selectivity index in favor of HO-2. The present study has revealed additional candidates based on inhibition of heme oxygenases for potentially useful pharmacological and therapeutic applications.
An efficient and convenient method for synthesis of 1-substituted imidazoles
Lin, Chun Min,Wong, Fung Fuh,Huang, Jiann-Jyh,Yeh, Mou-Yung
, p. 1359 - 1370 (2007/10/03)
A convenient method for the synthesis 1-substituted imidazoles was developed by the reaction of α-bromoketone with lithium imidazolide. The reaction gave the desired products in improved yields without the formation of 1,3-disubstituted imidazolium salts. Treatment of bromoacetaldehyde ethylene acetal, 2-(bromomethyl)tetrahydro-2H-pyran, and N-(bromomethyl)phthalimide with lithium imidazolide also gave the corresponding 1-substituted imidazole in good to excellent yields. Direct reaction of α-bromoketone with imidazole as control experiment afforded undesired 1,3-disubstituted imidazolium salts with the desired mono-substituted products.
N-substituted-imidazoles as inhibitors of nitric oxide synthase: A preliminary screening
Salerno,Sorrenti,Guerrera,Sarva,Siracusa,Di Giacomo,Vanella
, p. 685 - 690 (2007/10/03)
Identification of potent and selective inhibitors of inducible or neuronat nitric oxide synthase (NOS) is of great interest because of their therapeutic potential for treatment of diseases mediated by overproduction of nitric oxide. Imidazole derivatives
Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(ω-phenyl-ω-hydroxyalkyl)imidazoles
Nardi,Tajana,Leonardi,Pennini,Portioli,Magistretti,Subissi
, p. 727 - 731 (2007/10/02)
A novel series of N-(benzoylalkyl)imidazoles and N-(ω-phenyl-ω-hydroxyalkyl)imidazoles was synthesized and evaluated for anticonvulsant activity in mice against maximal electroshock induced seizures. Some of the compounds showed an activity comparable to or better than phenytoin and phenobarbital. The N-[β-[4-(β-phenylethyl)phenyl]-β-hydroxyethyl]imidazole (38) was selected for further studies; preclinical toxicology and additional efficacy evaluations are in progress. Structure-activity relationships are discussed.
