6501-72-0

Basic information

• Product Name: 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid
• Synonyms: 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid;GIT 27;VGX-1027;3-Phenyl-2-isoxazoline-5-acetic acid;VGX 1027 3-Phenyl-2-isoxazoline-5-acetic acid;(S,R)-3-Phenyl-4,5-dihydro-5-isoxasole acetic acid;2-Isoxazoline-5-acetic acid, 3-phenyl-;5-Isoxazoleacetic acid, 4,5-dihydro-3-phenyl-
• CAS NO: 6501-72-0
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205
• Product Categories: Inhibitors
• Mol File: 6501-72-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 157-158℃
• Appearance: /
• Storage Temp.: Store at +4°C
• Solubility: Soluble in DMSO (up to 30 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid(6501-72-0)
• EPA Substance Registry System: 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid(6501-72-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• Hazardous Substances Data: 6501-72-0(Hazardous Substances Data)

Usage

Description

4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid, also known as VGX-1027, is an immunomodulator that selectively inhibits the secretion of pro-inflammatory cytokines such as IL-1β, TNF-α, and IL-10 from activated macrophages while sparing T cell function. It has been shown to ameliorate the course of acute and chronic immunoinflammatory conditions in various mouse models and displays protective effects in particulate matter-induced acute lung injury by blocking TLR4 signaling.

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 articles and documents

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

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