ChemicalBook--->CAS DataBase List--->6501-72-0

6501-72-0

6501-72-0 Structure

6501-72-0 Structure
IdentificationBack Directory
[Name]

4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid
[CAS]

6501-72-0
[Synonyms]

GIT 27
CS-1488
VGX-127
VGX-1027
VGX-1027, >=98%
VGX-1027(GIT 27)
VGX-1027, 6501-72-0
3-Phenyl-2-isoxazoline-5-acetic acid
2-Isoxazoline-5-acetic acid, 3-phenyl-
GIT27; GIT27; GIT-27; VGX1027; VGX 1027
4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid
5-Isoxazoleacetic acid, 4,5-dihydro-3-phenyl-
2-(3-PHENYL-4,5-DIHYDROISOXAZOL-5-YL)ACETIC ACID
(3-Phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid
(S,R)-3-Phenyl-4,5-dihydro-5-isoxasole acetic acid
2-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid
VGX 1027 3-Phenyl-2-isoxazoline-5-acetic acid
[Molecular Formula]

C11H11NO3
[MDL Number]

MFCD08696167
[MOL File]

6501-72-0.mol
[Molecular Weight]

205
Chemical PropertiesBack Directory
[Melting point ]

157-158℃
[storage temp. ]

Store at +4°C
[solubility ]

Soluble in DMSO (up to 30 mg/ml).
[form ]

solid
[color ]

White
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22-43
[Safety Statements ]

36/37
[HS Code ]

2934.99.4400
Hazard InformationBack Directory
[Description]

VGX-1027 (6501-72-0) is an immunomodulator that inhibits secretion of IL-1β, TNF-α, and IL-10 from murine macrophages stimulated with LPS and spares T cell function.1?Ameliorates the course of acute and chronic immunoinflammatory conditions such as carrageenan-induced pleurisy, LPS-induced lethality, and type II collagen-induced arthritis in mouse models.1?Prevents spontaneous and accelerated forms of autoimmune diabetes in a NOD mouse model.2?Modulates genes involved in LPS-induced Toll-like receptor 4 activation in a mouse Lupus model.3?Displays protective effects in particulate matter-induced acute lung injury by blocking TLR4 signaling.4
[Uses]

2-(3-Phenyl-4,5-dihydroisoxazol-5-yl)acetic Acid reduces the secretion of IL-1β, TNF-α and IL-10 from purified murine macrophages but not of T cells; and reduces the activation of NF-κB and p38 MAP kinase pathways along with up-regulation of ERK pathways. 2-(3-Phenyl-4,5-dihydroisoxazol-5-yl)acetic Acid inhibits proliferation of enterobacterial antigen-reactive CD4+CD25- T cells in vitro .
[in vivo]

VGX-1027 (10, 20 mg/kg of i.p. for 12 day or 100 mg/kg of p.o. for 11 day) successfully counteractes the development of destructive insulitis and hyperglycemia[1].
VGX-1027 (25?mg/kg; ip; single dose) counteracts the uveitis-inducing effect of LPS in eight-week-old male Lewis rats (180-220?g)[3].

Animal Model:Adult male mice, at 6 to 8 weeks of age with 25 to 30 g[1]
Dosage:10, 20 mg/kg for i.p. or 100 mg/kg for p.o.
Administration:IP daily for 12 consecutive day or PO daily for 11 consecutive day
Result:Successfully counteracted the development of destructive insulitis and hyperglycemia to the mice made diabetic with multiple low doses of Streptozotocin.
[IC 50]

IL-1β; IL-10
[storage]

Store at +4°C
[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
Spectrum DetailBack Directory
[Spectrum Detail]

4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid(6501-72-0)1HNMR
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