N6022

Base Information

• Chemical Name: N6022
• CAS No.: 1208315-24-5
• Molecular Formula: C₂₄H₂₂N₄O₃
• Molecular Weight: 414.464
• Mol file: 1208315-24-5.mol

Synonyms:3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrole -2-yl)propionic acid

Chemical Property of N6022

Chemical Property:

• Boiling Point: 662.7±55.0 °C(Predicted)
• PKA: 4.63±0.10(Predicted)
• Density: 1.30±0.1 g/cm3(Predicted)
• Storage Temp.: -20° C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml).

Purity/Quality:

98% min ^*data from raw suppliers

N6022 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: N6022 (1208315-24-5) is a potent and reversible inhibitor of S-nitrosoglutathione reductase (GSNOR) – IC50?= 20 nM1, 8 nM2. It demonstrated significant efficacy in mouse models of ovalbumin-induced asthma, chronic obstructive pulmonary disease, and irritable bowel syndrome. N6022 was able to attenuate experimental autoimmune encephalomyelitis (an animal model of multiple sclerosis)?via?selective inhibition of pro-inflammatory CD4+?cells (TH1/TH17) while upregulating anti-inflammatory subsets of CD4+?cells (TH2/Treg) without causing lymphopenia.3
• Uses: N6022 is a tight-binding, specific, and fully reversible inhibitor of S-nitrosoglutathione reductase.

Technology Process of N6022

There total 6 articles about N6022 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: 55.0%

ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate → 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrole -2-yl)propionic acid (1208315-24-5)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; for 5h;

Reference yield:

para-bromoacetophenone (99-90-1) → 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrole -2-yl)propionic acid (1208315-24-5)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol; sodium methylate / 20 °C

2: hydrogen bromide / water; ethanol / 8 h / Reflux

3: toluene-4-sulfonic acid / ethanol / Reflux

4: L-proline; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 100 °C / Inert atmosphere

5: lithium hydroxide monohydrate; water / tetrahydrofuran / 5 h / 20 °C

With methanol; copper(l) iodide; lithium hydroxide monohydrate; water; hydrogen bromide; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; L-proline; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide;

Reference yield:

1-(4-bromophenyl)-3-(furan-2-yl)-2-propen-1-one (132434-53-8,36715-58-9) → 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrole -2-yl)propionic acid (1208315-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen bromide / water; ethanol / 8 h / Reflux

2: toluene-4-sulfonic acid / ethanol / Reflux

3: L-proline; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 100 °C / Inert atmosphere

4: lithium hydroxide monohydrate; water / tetrahydrofuran / 5 h / 20 °C

With copper(l) iodide; lithium hydroxide monohydrate; water; hydrogen bromide; potassium carbonate; toluene-4-sulfonic acid; L-proline; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide;

upstream raw materials:

furfural

para-bromoacetophenone

1-(4-bromophenyl)-3-(furan-2-yl)-2-propen-1-one

ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate

Downstream raw materials:

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(2-methyl-4-(methylsulfonamido)phenyl)-1H-pyrrol-2-yl)propanoic acid

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-amino-2-methylphenyl)-1H-pyrrol-2-yl)propanoic acid

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(2-methyl-4-propionamidophenyl)-1H-pyrrol-2-yl)propanoic acid

Refernces