Bindarit

Base Information

• Chemical Name: Bindarit
• CAS No.: 130641-38-2
• Molecular Formula: C19H20N2O3
• Molecular Weight: 324.379
• Hs Code.: 2933990090
• Mol file: 130641-38-2.mol

Synonyms:2-[(1-Benzyl-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid;2-Methyl-2-((1-(phenylmethyl)-1H-indazol-3-yl)methoxy)propanoic acid;AF 2838;

Chemical Property of Bindarit

Chemical Property:

• Vapor Pressure: 1.28E-12mmHg at 25°C
• Refractive Index: 1.594
• Boiling Point: 542.869 °C at 760 mmHg
• PKA: 3.59±0.10(Predicted)
• Flash Point: 282.117 °C
• PSA: 64.35000
• Density: 1.188 g/cm³
• LogP: 3.46440
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Bindarit ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Bindarit is an inhibitor of monocyte chemoattractant protein (MCP) production that is selective for MCP-1/CCL2, MPC-3/CCL7, and MCP-2/CCL8 over other chemokines. It inhibits LPS- or C. albicans-induced production of MCP-1/CCL2 in isolated human monocytes (IC50s = 172 and 403 μM, respectively). Bindarit downregulates NF-κB signaling and prevents p65 and p65/p50-mediated MCP-1/CCL2 promoter activation in RAW264.7 cells. It delays the onset of proteinuria and prolongs survival in a mouse model of experimental lupus nephritis when administered at a dose of 50 mg/kg. It prevents LPS-induced increases in MCP-1/CCL2 expression in mouse brain and spinal cord when administered at a dose of 200 mg/kg and reduces the incidence and severity of experimental autoimmune encephalomyelitis (EAE) in mice. Bindarit is also a noncompetitive inhibitor of monocarboxylate transporter 4 (MCT4; Ki = 30.2 μM for the human transporter) that is selective for MCT4 over MCT1.
• Uses: Bindarit shows anti-inflammatory activity due to a selective inhibition of a subfamily of inflammatory chemokines. Bindarit is a also protein antidenaturant agent. Bindarit modulates the NFkB pathway and has been shown to reduce secondary phase of adjuvant arthritis in rats. Bindarit exhibits selective inhibition against monocyte chemotactic proteins MCP-1/CCL2, MCP-3/CCL7 and MCP-2/CCL8.

Technology Process of Bindarit

There total 10 articles about Bindarit 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: 88.7%

1-benzyl-3-chloromethyl-1H-indazole (131427-22-0) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid (130641-38-2)

Guidance literature:

ethyl 2-hydroxy-2,2-dimethylethanoate; With sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 5 ℃; for 1.5h; Inert atmosphere;

1-benzyl-3-chloromethyl-1H-indazole; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 25 ℃; for 10h; Inert atmosphere;

Reference yield:

C21H24N2O3 → 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid (130641-38-2)

Guidance literature:

C₂₁H₂₄N₂O₃; With sodium hydroxide; for 3h; Reflux;

With hydrogenchloride; In water;

Reference yield:

N-benzyl-3-iodo-1H-indazole (205643-28-3) → 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid (130641-38-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: isopropylmagnesium chloride / 2-methyltetrahydrofuran / 2 h / -10 °C / Inert atmosphere

1.2: 2 h / 0 °C

2.1: hydrogenchloride / toluene; water / 2 h / 90 °C

3.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere

3.2: 10 h / 90 °C

4.1: sodium hydroxide / 3 h / Reflux

With hydrogenchloride; isopropylmagnesium chloride; sodium hydride; sodium hydroxide; In 2-methyltetrahydrofuran; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

benzyl bromide

3-bromo-1H-indazole

(1-Benzyl-1H-indazol-3-yl)-methanol

1-benzyl-3-chloromethyl-1H-indazole

Downstream raw materials:

1-benzyl-3-[(1,1-dimethyl-2-morpholin-4-ylethoxy)methyl]-1H-indazole.

2-[(1-benzyl-5-bromo-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid

2-[(1-benzyl-5-chloro-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid

2-[(1-benzyl-1H-indazol-3-yl)methoxy]-2-methylpropan-1-ol

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF 1-BENZYL-3-HYDR0XYMETHYL-1H-INDAZ0LE AND ITS DERIVATIVES AND REQUIRED MAGNESIUM INTERMEDIATES". . . Retrieved 2011/02/24.
• 2、 -. "NOVEL 1-BENZYL-3-HYDROXYMETHYLINDAZOLE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF DISEASES BASED ON THE EXPRESSION OF MCP-1, CX3CR1 AND P40". Page/Page column 32-33. . Retrieved 2009/10/22.