Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]-

Base Information

• Chemical Name: Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]-
• CAS No.: 530141-72-1
• Molecular Formula: C₂₉H₂₇NO₈
• Molecular Weight: 517.535
• Mol file: 530141-72-1.mol

Synonyms:3-[5-[4-(Cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionic acid;

Chemical Property of Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]-

Chemical Property:

• PKA: 4.61±0.10(Predicted)
• PSA: 139.32000
• Density: 1.376±0.06 g/cm3(Predicted)
• LogP: 5.38760

Purity/Quality:

97% ^*data from raw suppliers

T-5224 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: T-5224 is an inhibitor of c-fos/activator protein 1 (AP-1). It inhibits the DNA binding activity of c-fos/AP-1 without affecting the activity of C/EBPα, ATF2, MyoD, Sp1, and NF-κB/p65 in vitro. It shows inhibitory activity in a c-fos/AP-1 promoter luciferase assay without changing c-fos family protein expression levels in TNF-α-stimulated NIH/3T3 cells. Administration of T-5224 (30 mg/kg) inhibits the development of collagen-induced arthritis in mice through reduction of IL-1β production, neutrophil infiltration, and synovial cell proliferation. It reduces the inflammatory cytokine response in LPS-challenged mice, lowering levels of TNF-α and HMGB1 in the serum and MIP-1α and MCP-1 in the liver. T-5224 reduces in vivo necrosis of liver tissue and improves survival rates in LPS-challenged mice. T-5224 also exhibits anticancer activity, reducing proliferation and migration of HSC-3-M3 head and neck squamous carcinoma cells in vitro and the number of metastases in an HSC-3-M3 orthotopic xenograft model in vivo.
• Uses: T-5224 is a selective activator protein-1 inhibitor that prevents lymph node metastasis in an oral cancer model.

Technology Process of Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]-

There total 16 articles about Benzenepropanoic acid, 5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(2,3-dihydro-3-oxo-1,2-benzisoxazol-6-yl)methoxy]- 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: 84.0%

3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-trityl-2,3-dihydro-1,2-benzisoxazol-6-yl)methoxy]phenyl} propanoic acid → T-5224 (530141-72-1)

Guidance literature:

With acetic acid; In water; at 20 ℃; for 46h;

Reference yield:

methyl 3-[5-(2,4-dimethoxybenzoyl)-2-methoxyphenyl] propanoate → T-5224 (530141-72-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Pyridine hydrobromide; sodium chloride / 1 h / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 10 h / 82 °C

3: sodium hydroxide; water / ethanol / 3 h / 20 - 70 °C

4: thionyl chloride / 3.33 h / Cooling with ice

5: potassium carbonate / acetone / 5.5 h / 68 °C / Inert atmosphere

6: sodium hydroxide; water / ethanol / 60 °C

7: acetic acid / water / 46 h / 20 °C

With thionyl chloride; water; Pyridine hydrobromide; potassium carbonate; acetic acid; sodium chloride; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetone;

Reference yield:

6-(2,4-dihydroxybenzoyl)-2-chromanone (530141-56-1) → T-5224 (530141-72-1)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 82 °C

2: sodium hydroxide; water / ethanol / 3 h / 20 - 70 °C

3: thionyl chloride / 3.33 h / Cooling with ice

4: potassium carbonate / acetone / 5.5 h / 68 °C / Inert atmosphere

5: sodium hydroxide; water / ethanol / 60 °C

6: acetic acid / water / 46 h / 20 °C

With thionyl chloride; water; potassium carbonate; acetic acid; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

6-(2,4-dihydroxybenzoyl)-2-chromanone

6-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-chromanone

2-methoxy-benzenepropanoic acid

methyl 3-[2-hydroxy-5-(2-hydroxy-4-cyclopentyloxybenzoyl)phenyl]propionate