4,5-Dihydro-3-phenyl-5-isoxazoleacetic acid

Base Information

• Chemical Name: 4,5-Dihydro-3-phenyl-5-isoxazoleacetic acid
• CAS No.: 6501-72-0
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• European Community (EC) Number: 636-241-9
• UNII: AKT814N13R
• DSSTox Substance ID: DTXSID50445023
• Wikipedia: VGX-1027
• Wikidata: Q104760824
• NCI Thesaurus Code: C184883
• ChEMBL ID: CHEMBL1320667
• Mol file: 6501-72-0.mol

Synonyms:(S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid;3-phenyl-4,5-dihydro-5-isoxazole acetic acid;GIT27;VGX-1027

Chemical Property of 4,5-Dihydro-3-phenyl-5-isoxazoleacetic acid

Chemical Property:

• Melting Point: 157-158℃
• PSA: 58.89000
• LogP: 1.08990
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

99%, ^*data from raw suppliers

GIT 27 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(ON=C1C2=CC=CC=C2)CC(=O)O
• Recent ClinicalTrials: GLS-1027 for the Prevention of Severe Pneumonitis Caused by SARS-CoV-2 Infection (COVID-19)
• Recent EU Clinical Trials: Safety, Tolerability, Efficacy and Dose Response of GLS-1027 in the Prevention of Severe Pneumonitis caused by SARS-CoV-2 Infection
• 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 .

Technology Process of 4,5-Dihydro-3-phenyl-5-isoxazoleacetic acid

There total 11 articles about 4,5-Dihydro-3-phenyl-5-isoxazoleacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

3-phenyl-5-vinyl-4,5-dihydroisoxazole (92287-44-0) → (S,R)-3-phenyl-4,5-dihydro-5-isoxasoleacetic acid (6501-72-0)

Guidance literature:

3-phenyl-5-vinyl-4,5-dihydroisoxazole; With dimethylsulfide borane complex; In dichloromethane; at 0 - 20 ℃; for 3h;

With chromium(VI) oxide; water; acetic acid; In dichloromethane; at 5 ℃; for 12h;

DOI:10.1021/acs.orglett.1c01897

Reference yield:

C7H8ClNO (1378834-78-6) + but-3-enoic acid (625-38-7) → (S,R)-3-phenyl-4,5-dihydro-5-isoxasoleacetic acid (6501-72-0)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; for 12h;

Reference yield:

acetophenone oxime (613-91-2) → (S,R)-3-phenyl-4,5-dihydro-5-isoxasoleacetic acid (6501-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) hexane, THF,- 20 deg C, 1 h, 2.) THF, 0 deg C, 1 h, and room temperature, 16 h.

2: dimethylformamide; H₂O / 0.5 h / Heating

With n-butyllithium; In water; N,N-dimethyl-formamide;

DOI:10.1080/00397919708004145

upstream raw materials:

but-3-enoic acid

benzohydroximoyl chloride

acetophenone oxime

C₇H₈ClNO

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