6501-72-0

Usage

Uses

Used in Immunoinflammatory Conditions:
4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid is used as an immunomodulator for the treatment of acute and chronic immunoinflammatory conditions such as carrageenan-induced pleurisy, LPS-induced lethality, and type II collagen-induced arthritis in mouse models. It modulates genes involved in LPS-induced Toll-like receptor 4 activation, providing a potential therapeutic approach for conditions like Lupus.
Used in Autoimmune Diabetes:
4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid is used as a preventive agent for the development of spontaneous and accelerated forms of autoimmune diabetes in a NOD mouse model, offering a potential treatment strategy for diabetes management.
Used in Inflammation and Immune Response:
4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid is used as an inhibitor of the secretion of IL-1β, TNF-α, and IL-10 from purified murine macrophages, reducing the activation of NF-κB and p38 MAP kinase pathways along with up-regulation of ERK pathways. This makes it a potential candidate for modulating the immune response in various inflammatory conditions.
Used in Inhibition of T Cell Proliferation:
4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid is used as an inhibitor of the proliferation of enterobacterial antigen-reactive CD4+CD25T cells in vitro, suggesting its potential use in controlling T cell-mediated immune responses.

References

1) Stojanovic?et al.?(2007),?In vitro, ex vivo and in vivo immunopharmacological activities of the isooxazoline compound VGX-1027: modulation of cytokine synthesis and prevention of both organ-specific and systemic autoimmune diseases in murine models; Clin. Immunol.,?123?311 2) Stosic-Grujisic?et al.?(2007),?A potent immunomodulatory compound, (S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid, prevents spontaneous and accelerated forms of autoimmune diabetes in NOD mice and inhibits the immunoinflammatory diabetes induced by multiple low doses of streptozotocin in CBA/H mice; J. Pharmacol. Exp. Ther.,?320?1038 3) Fagone?et al.?(2014),?VGX-1027 modulates genes involved in lipopolysaccharide-induced Toll-like receptor 4 activation and in a murine model of systemic lupus erythematosus; Immunology,?142?594 4) Xu?et al.?(2019),?Protective effects of VGX-1027 in PM2.5-induced airway inflammation and bronchial hyperresponsiveness; Eur. J, Pharmacol.,?842?373

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Relevant academic research and scientific papers

A potent immunomodulatory compound, (S,R)-3-Phenyl-4,5-dihydro-5-isoxasole acetic acid, prevents spontaneous and accelerated forms of autoimmune diabetes in NOD mice and inhibits the immunoinflammatory diabetes induced by multiple low doses of streptozoto

(S,R)-3-Phenyl-4,5-dihydro-5-isoxasole acetic acid (VGX-1027) is an isoxazole compound that exhibits various immunomodulatory properties. The capacity of VGX-1027 to prevent interleukin (IL)-1β plus interferon-γ-induced pancreatic islet death in vitro pro

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

COMPOUNDS HAVING IMMUNOMODULATOR ACTIVITY

Compounds of formula I wherein I, R1-5 represents from one to five substituents independently selected from hydrogen, nitro, cyano, C1-C3-alkyl, halogen, carboxy, amino, trifluoromethyl, hydroxy, C1-C3/sub

A convenient synthesis of 3- and 3,4-substituted 4,5-dihydroisoxazole- 5-acetic acids

The 4,5-dihydroisoxazole-5-acetic acids 4a-j were prepared from the ketoximes la-j, 2,2-dimethyl-5-methoxymethylene-l,3-dioxan-4,6-dione (2) and butyllithium in yields from 35 to 79 %.