5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester

Base Information

• Chemical Name: 5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester
• CAS No.: 478336-92-4
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.24
• Hs Code.: 2934999090
• UNII: 7QFF3Z0V9X
• ChEMBL ID: CHEMBL210858
• Nikkaji Number: J2.335.058K
• Wikidata: Q27268714
• Mol file: 478336-92-4.mol

Synonyms:ISO-1;478336-92-4;MIF Antagonist, ISO-1;methyl 2-(3-(4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)acetate;MIF Antagonist;5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester;7QFF3Z0V9X;ISO 1;CHEMBL210858;MFCD22376813;4,5-DIHYDRO-3-(4-HYDROXYPHENYL)-5-ISOXAZOLEACETIC ACID, METHYL ESTER;4,5-dihydro-3-(4-hydroxyphenyl)-5-isoxazoleacetic acid, methyl ester;METHYL 2-[3-(4-HYDROXYPHENYL)-4,5-DIHYDRO-1,2-OXAZOL-5-YL]ACETATE;UNII-7QFF3Z0V9X;Methyl 2-[3-(4-Hydroxyphenyl)-4,5-dihydroisoxazol-5-yl]acetate;IN1228;ISO1;ISO-1, MIF Antagonist;SCHEMBL668287;GTPL9984;HMS3747E11;BCP15471;EX-A2475;BDBM50186426;s7732;AKOS016011552;CCG-266827;CS-3224;US8618147, ISO-1;NCGC00379103-02;AC-36089;AS-53744;HY-16692;SY245019;I1119;P17039;Macrophage Migration Inhibitory Factor Antagonist;EN300-19054503;Macrophage Migration Inhibitory Factor;Q27268714;3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic methyl ester;4,5-Dihydro-3-(4-hydroxyphenyl)-5-isoxazoleacetic acid methyl ester;methyl 2-[3-(4-oxo-1-cyclohexa-2,5-dienylidene)-1,2-oxazolidin-5-yl]acetate

Chemical Property of 5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester

Chemical Property:

• Melting Point: 114 °C
• Boiling Point: 365.0±48.0 °C(Predicted)
• PKA: 9.22±0.30(Predicted)
• PSA: 64.63000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 1.12100
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

MIF-Antagonist, ISO-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1CC(=NO1)C2=CC=C(C=C2)O
• Description: ISO-1 (478336-92-4) is an antagonist of macrophage migration inhibitory factor (MIF, a pro-inflammatory cytokine). Displays anti-inflammatory activity. Increases survival in severe sepsis.1 Inhibits airway remodeling in mouse asthma model.2 ISO-1 also blocks MIF-induced autophagy.3?Active in cellular and mouse models.
• Uses: MIF Antagonist, ISO-1 inhibits MIF dopachrome tautomerase activity by binding to its catalytic active site (IC50 = 7 μM for D-dopachrome tautomerase) and suppresses the production of TNFα, PGE2 and COX-2 in human monocytes and arachidonic acid in RAW 264.7 macrophages. MIF Antagonist, ISO-1 has been shown to exhibit antidiabetogenic properties in immunoinflammatory diabetic mouse model.

Technology Process of 5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester

There total 13 articles about 5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester 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: 98.0%

methyl 3-(p-t-butyldiphenylsilyloxyphenyl)-5-isoxazolinylacetate (904672-55-5) → methyl 2-(3-(4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)acetate (478336-92-4)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In dichloromethane; water;

DOI:10.1002/jhet.5570430303

Reference yield: 21.0%

1-(4-hydroxyphenyl)but-3-en-1-one oxime + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl 2-(3-(4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)acetate (478336-92-4)

Guidance literature:

With copper dichloride; palladium dichloride; under 760 Torr;

DOI:10.1002/jhet.5570430303

Reference yield:

1-[4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-but-3-en-1-one (904672-63-5) → methyl 2-(3-(4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)acetate (478336-92-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₂OH*HCl; NaOAc / ethanol; H₂O / Heating

2: KF; 18-crown-6 / CH₂Cl₂; H₂O

3: 21 percent / CuCl₂ / PdCl₂ / 760 Torr

With potassium fluoride; 18-crown-6 ether; hydroxylamine hydrochloride; sodium acetate; copper dichloride; palladium dichloride; In ethanol; dichloromethane; water;

DOI:10.1002/jhet.5570430303

upstream raw materials:

methyl 3-(p-t-butyldiphenylsilyloxyphenyl)-5-isoxazolinylacetate

methanol

carbon monoxide

1-(4-hydroxy-phenyl)-but-3-en-1-one

Downstream raw materials:

C₁₂H₁₃NO₄*C₁₉H₂₂N₂O

C₁₂H₁₃NO₄*C₁₉H₂₂N₂O

C₂₄H₂₄N₂O₇