- Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines
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A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional groups. Control experiments support a nitrile oxide intermediate mechanism for this novel class of oxidative cyclization reactions. Moreover, synthetic applications toward bioactive molecular skeletons and the late-stage modification of drugs were realized.
- Zhang, Xiao-Wei,He, Xiao-Lin,Yan, Nan,Zheng, Hong-Xing,Hu, Xiang-Guo
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p. 15726 - 15735
(2020/11/30)
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- Development of a continuous flow photoisomerization reaction converting isoxazoles into diverse oxazole products
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A continuous flow process is presented, which directly converts isoxazoles into their oxazole counterparts via a photochemical transposition reaction. This results in the first reported exploitation of this transformation to establish its scope and synthe
- Bracken, Cormac,Baumann, Marcus
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p. 2607 - 2617
(2020/03/11)
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- ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF
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A compound of Formula (I) or or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating hearing loss or balance disorder: Formula (I) wherein R1 and Y are as defined herein.
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- ISOXAZOLE CARBOXAMIDE COMPOUNDS AND USES THEREOF
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A compound of Formula (I)) or or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating hearing loss or balance disorder: wherein R1 through R3, and L are as defined herein.
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- PYRADAZINONE DERIVATIVES AND THE COMPOSITIONS AND METHODS OF TREATMENT REGARDING THE SAME
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The present disclosure is directed to pyridazin-3(2H)-one compounds of formula (I), pharmaceutical compositions thereof and methods for modulating or activating a Parkin ligase The present disclosure is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase, R21, R22, R23, R24 and R25 are as defined herein.
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Paragraph 488; 491-492
(2018/01/17)
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- Synthesis and evaluation as antitubercular agents of 5-arylethenyl and 5-(hetero)aryl-3-isoxazolecarboxylate
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Preclinical Research A new series of 5-aryl and 5-arylethenylisoxazole carboxylate derivatives was synthesized and evaluated for in vitro activity against Mycobacterium tuberculosis H37Rv. Several compounds exhibited minimum inhibitory concentrations in the low micromolar range (2.3-11.4 μM). A variety of substituents introduced around the isoxazole ring allowed the delineation of preliminary SARs for this new series of compounds.
- Vergelli, Claudia,Cilibrizzi, Agostino,Crocetti, Letizia,Graziano, Alessia,Dal Piaz, Vittorio,Wan, Baojie,Wang, Yuehong,Franzblau, Scott,Giovannoni, Maria Paola
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p. 162 - 172
(2013/05/22)
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- Molecular recognition at the active site of factor Xa: Cation-π Interactions, stacking on planar peptide surfaces, and replacement of structural water
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Factor Xa, a serine protease from the blood coagulation cascade, is an ideal enzyme for molecular recognition studies, as its active site is highly shape-persistent and features distinct, concave sub-pockets. We developed a family of non-peptidic, small-molecule inhibitors with a central tricyclic core orienting a neutral heterocyclic substituent into the S1 pocket and a quaternary ammonium ion into the aromatic box in the S4 pocket. The substituents were systematically varied to investigate cation-π interactions in the S4 pocket, optimal heterocyclic stacking on the flat peptide walls lining the S1 pocket, and potential water replacements in both the S1 and the S4 pockets. Structure-activity relationships were established to reveal and quantify contributions to the binding free enthalpy, resulting from single-atom replacements or positional changes in the ligands. A series of high-affinity ligands with inhibitory constants down to Ki=2nM were obtained and their proposed binding geometries confirmed by X-ray co-crystal structures of protein-ligand complexes. Factor Xa is an ideal enzyme to undertake molecular recognition studies at atomic level resolution as its active site is completely conserved in complexes with designed ligands. Cation-π interactions, water replacements, and stacking interactions with flat peptide fragments were investigated, revealing large changes in binding affinity resulting from single-atom mutations or positional shifts of heteroatoms in the ligands. Copyright
- Salonen, Laura M.,Holland, Mareike C.,Kaib, Philip S. J.,Haap, Wolfgang,Benz, J?rg,Mary, Jean-Luc,Kuster, Olivier,Schweizer, W. Bernd,Banner, David W.,Diederich, Fran?ois
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p. 213 - 222
(2012/03/09)
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- Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches
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(figure presented) Regioselective 1,3-dipolar cycloadditions of supported vinyl ethers R1C(=CH2)O-CH2-polymer, prepared by the Tebbe olefination of R1CO2-CH2-polymer with ethyl cyanoformate
- Barrett, Anthony G. M.,Procopiou, Panayiotis A.,Voigtmann, Ulrike
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p. 3165 - 3168
(2007/10/03)
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