53370-50-6Relevant academic research and scientific papers
Scalable and Safe Transformation of 3-Hydroxypropionitrile to Its Amidoxime
Hlubb, Leah N.,Johnson, Eric C.,Sabatini, Jesse J.,Orlicki, Joshua A.
, p. 195 - 198 (2022/01/20)
Scalable synthesis of amidoxime 1 by nucleophilic addition of 50% aq. NH2OH to 3-hydroxypropionitrile is reported. In the presence of hydroxyl and amidoxime moieties, this dually functional compound can be manipulated for the synthesis of heterocyclic compounds that may be useful for the energetic materials and pharmaceutical chemistry communities. In preparing 1, it was discovered that previously published procedures were either irreproducible and/or the processes were not practical on larger scales. Previously published procedures required flash chromatography and/or afforded the amidoxime product in a low yield. The improved method discussed in this paper involves rotary evaporation of the completed reaction mixture to remove excess water, followed by trituration in acetone to obtain 83–90% yields. This method has been carried out multiple times on the 86–94 g scale, with minimal exothermic activity detected.
Synthesis of isoxazoline derivatives through boulton-katritzky rearrangement of 1,2,4-oxadiazoles
Palumbo Piccionello, Antonio,Guarcello, Annalisa,Pace, Andrea,Buscemi, Silvestre
, p. 1986 - 1992 (2013/05/09)
The base-induced rearrangement of 1,2,4-oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three-atom side-chain rearrangement that involves a saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken. The first example of a Boulton-Katritzky Rearrangement that involves an oxadiazole ring with a saturated CCO side chain is reported. From a mechanistic point of view, the results present a new and interesting feature of this reaction. Because of the presence of a stable intermediate, this rearrangement affords nonaromatic isoxazolines.
Discovery of N-{5-[3-(3-hydroxypiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-4- methyl-1,3-thiazol-2-yl}acetamide (TASP0415914) as an orally potent phosphoinositide 3-kinase γ inhibitor for the treatment of inflammatory diseases
Oka, Yusuke,Yabuuchi, Tetsuya,Oi, Takahiro,Kuroda, Shoichi,Fujii, Yasuyuki,Ohtake, Hidenori,Inoue, Tomoyuki,Wakahara, Shunichi,Kimura, Kayo,Fujita, Kiyoko,Endo, Mayumi,Taguchi, Kyoko,Sekiguchi, Yoshinori
, p. 7578 - 7583 (2014/01/06)
Class I phosphoinositide 3-kinases (PI3Ks), particularly PI3Kγ, have become attractive drug targets for inflammatory and autoimmune disorders such as rheumatoid arthritis. Herein, we describe the synthesis and the structure-activity relationships (SAR) of a series of 2-amino-5-oxadiazolyl thiazoles, culminating in the identification of 8j (TASP0415914), an orally potent inhibitor of phosphoinositide 3-kinase γ (PI3Kγ). TASP0415914 demonstrated good potency in a cell-based assay and, furthermore, exhibited in vivo efficacy in a collagen induced arthritis (CIA) model in mice after oral administration.
SUBSTITUTED PIPERIDINES
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Page/Page column 16, (2010/12/29)
The invention relates to novel substituted piperidines, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular diseases and tumour diseases.
NOVEL NITRILE AND AMIDOXIME COMPOUNDS AND METHODS OF PREPARATION
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, (2009/05/28)
The present application relates to semiconductor processing compositions comprising at least one compound containing at least one amidoxime functional group and to methods of using these compositions in semiconductor processing. The present application also describes the preparation of amidoximes for a semiconductor processing composition by (a) mixing a cyanoethylation catalyst, a nucleophile and an alpha-unsaturated nitrile to produce a cyanoethylation product; and (b) converting a cyano group in the cyanoethylation product into an amidoxime functional group.
STABILIZATION OF HYDROXYLAMINE CONTAINING SOLUTIONS AND METHOD FOR THEIR PREPARATION
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Page/Page column 20, (2009/05/28)
The invention relates to the use of amidoximes for prevention of or stabilization of hydroxylamine compounds against undesired decomposition.
Azole phenoxy hydroxyureas as selective and orally active inhibitors of 5- lipoxygenase
Malamas,Carlson,Grimes,Howell,Glaser,Gunawan,Nelson,Kanzelberger,Shah,Hartman
, p. 237 - 245 (2007/10/03)
Azole phenoxy hydroxyureas are a new class of 5-lipoxygenase (5-LO) inhibitors. Structure-activity relationship studies have demonstrated that electronegative substituents on the 2-phenyl portion of the oxazole tail increased the ex vivo potency of these
Tetrahydropyridyloxadiazoles: Semirigid Muscarinic Ligands
Showell, Graham A.,Gibbons, Tracey L.,Kneen, Clare O.,MacLeod, Angus M.,Merchant, Kevin,et al.
, p. 1086 - 1094 (2007/10/02)
Recent studies have described novel azabicycle-based muscarinic agonists which readily penetrate into the central nervous system and are capable of displaying high efficacy at cortical sites.The current paper describes the synthesis and biochemical assesment of semirigid muscarinic ligands which were used to map the requirements of the cortical muscarinic receptor and to study the degree of conformational flexibility required to cause receptor activation.Analogues 6 and 9 provide high-efficacy muscarinic agonist at cortical sites; however, C-alkylation on the tetrahydropyridine ring resulted in more rigid analogues and showed lower predicted efficacy.Molecular mechanics calculations indicated a preference for the E rotameric form.This conformation was also observed in the X-ray crystal structure of ethenyloxadiazole 12.The new compounds were tested in biochemical assay designed to measure receptor affinity and to predict cortical efficacy.
