110164-84-6Relevant articles and documents
The biological targets of acivicin inspired 3-chloro- and 3-bromodihydroisoxazole scaffolds
Orth, Ronald,Boettcher, Thomas,Sieber, Stephan A.
, p. 8475 - 8477 (2010)
Target analysis of acivicin derived 3-halodihydroisoxazoles scaffolds in living non-pathogenic and pathogenic bacteria.
Palladium-free Sonogashira-type cross-coupling reaction of bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes
Probst,Deprez,Willand
supporting information, p. 1066 - 1070 (2018/03/26)
A Cu(I)-catalysed Sonogashira-type cross coupling reaction with aliphatic or aromatic bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes is reported. The protocol we developed employs catalytic amount of copper(I), non-toxic ligand bathophenanthroline and is tolerant to a wide range of functional groups and is therefore particulary adapted in the context of drug discovery.
Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes
Chen, Wenwen,Wang, Bo,Liu, Nan,Huang, Dayun,Wang, Xinyan,Hu, Yuefei
, p. 6140 - 6143 (2015/01/09)
A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.
Structure-activity relationship analysis of the selective inhibition of transglutaminase 2 by dihydroisoxazoles
Watts, R. Edward,Siegel, Mathew,Khosla, Chaitan
, p. 7493 - 7501 (2007/10/03)
Human transglutaminase 2 (TG2) is believed to play an important role in the pathogenesis of various human disorders including celiac sprue, certain neurological diseases, and some types of cancer. Selective inhibition of TG2 should therefore enable further investigation of its role in physiology and disease and may lead to effective clinical treatment. Recently we showed that certain 3-halo-4-,5-dihydroisoxazole containing compounds are selective inhibitors of human TG2 with promising pharmacological activities. Here, we present definitive evidence that this class of compounds targets the active site of human TG2. Structure-activity relationship studies have provided insights into the structural prerequisites for selectivity and have led to the discovery of an inhibitor with about 50-fold higher activity than a prototypical dihydroisoxazole inhibitor with good in vivo activity. A method for preparing enantiomerically enriched analogues was also developed. Our studies show that the 5-(S)-dihydroisoxazole is a markedly better inhibitor of human TG2 than its 5-(R) stereoisomer.
BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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Page/Page column 317, (2010/02/06)
The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.
Synthesis and pharmacological investigation of new chiral muscarinic antagonists
Carnielli,De Amici,De Micheli,Gianferrara,Maurich,Zacchigna,Grana,Boselli
, p. 21 - 27 (2007/10/02)
The two pairs of enantiomers of isoxazolidin-3-ones 3 and 4 were synthesized by means of Lipase PS-catalyzed hydrolyses of suitable racemic butyrates. The same butyrates were also employed as key intermediates in the preparation of racemic 3 and 4. The an
Nitrile oxides in medicinal chemistry. 5. Lipase PS-catalyzed resolution of a set of heterocyclic derivatives
Carrea,De Amici,De Micheli,Liverani,Carnielli,Riva
, p. 1063 - 1072 (2007/10/02)
Lipase from Pseudomonas cepacia (lipase PS) catalyzed the hydrolysis of a series of butyrates of racemic primary alcohols carrying a Δ2-isoxazoline or an isoxazolidin-3-one nucleus. Within this set of compounds, the enantiopreference of the cat
Nitrile Oxides in Medicinal Chemistry. 4. Chemoenzymatic Synthesis of Chiral Heterocyclic Derivatives
Amici, Marco De,Magri, Paolo,Micheli, Carlo De,Cateni, Francesca,Bovara, Roberto,et al.
, p. 2825 - 2829 (2007/10/02)
The two enantiomers of 3-bromo-5-(hydroxymethyl)-Δ2-isoxazoline (1) and 2-phenyl-5-(hydroxymethyl)-isoxazolidin-3-one (9) have been prepared in enantiomeric excess higher than 90percent by hydrolysis of the corresponding butyrates under the cat
BROMONITRILE OXIDE CYCLOADDITIONS IN WATER
Rohloff, John C.,Robinson, James III,Gardner, John O.
, p. 3113 - 3116 (2007/10/02)
Bromonitrile oxide can be generated homogeneously in water at acidic pH, allowing efficient cycloaddition with water soluble olefins and acetylenes.Allylammonium salts react with high regioselectivity and without the need for N-group protection. Keyword: Acivicin; transglutaminase; cysteine; 4,5-dihydroisoxazole; dibromonoformaldoxime.
NITRILE OXIDES IN MEDICINAL CHEMISTRY-- 2. SYNTHESIS OF THE TWO ENANTIOMERS OF DIHYDROMUSCIMOL
Amici, Marco De,Micheli, Carlo De,Misani, Valeria
, p. 1975 - 1986 (2007/10/02)
The cycloaddition of bromonitrile oxide to monosubstituted olefins has a high regioselectivity yielding 3-bomo-5-substituted isoxazolines contaminated by minor amounts (4-9percent) of the 4-substituted isomer.The adducts of bromonitrile oxide to allyl alcohol and N-protected allylamine were employed as key intermediates in the preparation of racemic dihydromuscimol (DHM).The synthesis of (R)-(-)- and (S)-(+)-DHM was accomplished by using the two diastereomers obtained by the cycloaddition of bromonitrile oxide to (S)-(+)-isopropylidene-3-buten-1,2-diol.The enantiomeric excess of R)-(-)- and (S)-(+)-DHM, determined by capillary GLC on the appropriate precursors, were 98.8 and >99.0 percent.A spectroscopic survey of the tautomerism of 3-hydroxyisoxazolines indicates the predominant or exclusive occurence of the NH form.
