68672-88-8Relevant academic research and scientific papers
Efficient and simple preparation of functionalized 1,1-dibromoenol phosphates
Kotek, Vladislav,Polk, Peter,Tobrman, Tom
, p. 405 - 412 (2016/02/16)
The preparation of functionalized 1,1-dibromoalkenyl phosphates is described. The protocol developed for their preparation is based on the generation of enolates from α,α-dibromoketones followed by a reaction with dialkyl chlorophosphates. The procedure t
Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
, p. 74 - 96 (2013/04/10)
The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
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.
