EW-7197

Base Information

• Chemical Name: EW-7197
• CAS No.: 1352608-82-2
• Molecular Formula: C22H18FN7
• Molecular Weight: 399.43
• Mol file: 1352608-82-2.mol

Synonyms:N-(2-fluorophenyl)-5-(6-methyl-2-pyridinyl)-4-[1,2,4]triazolo[1,5-a]pyridin-6-yl-1H-imidazole-2-methanamine;NOV-1301;TEW-7197;N-[[4-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl]methyl]-2-fluoroaniline

Chemical Property of EW-7197

Chemical Property:

• PKA: 8.51±0.10(Predicted)
• PSA: 83.79000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 4.31400
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

EW7197 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: EW-7197 is a novel ALK-5 kinase inhibitor as well as TGF-β Type I Receptor Kinase Inhibitor. Study has shown that it can potently inhibit the breast to lung metastasis. Mice study has demonstrated that EW-7197 inhibited Smad/TGFβ signaling, cell migration, invasion, and lung metastasis in MMTV/c-Neu mice and 4T1 orthotopic-grafted mice. EW-7197 also inhibited the epithelial-to-mesenchymal transition (EMT) in both TGFβ-treated breast cancer cells and 4T1 orthotopic-grafted mice. Furthermore, EW-7197 enhanced cytotoxic T lymphocyte activity in 4T1 orthotopic-grafted mice and increased the survival time of 4T1-Luc and 4T1 breast tumor-bearing mice. It can also inhibit hepatic, renal, and pulmonary fibrosis by blocking TGF-β/Smad and ROS signaling. Therefore, it is a potential antitumor reagent. EW-7197 is a potent inhibitor of activin receptor-like kinase 5 (ALK5, also known as TGF-β receptor type 1; IC50 = 12.9 nM). It also inhibits ALK2 and ALK4 at nanomolar concentrations. EW-7197 blocks TGF-β/Smad signaling, cell migration, invasion, and lung metastasis in mouse mammary tumor virus/c-Neu mice and 4TI orthotopic-grafted mice. It also inhibits epithelial-to-mesenchymal transition (EMT) in TGF-β-treated breast cancer cells. EW-7197 is used to block TGF-β signaling and EMT in animal models of cancer and fibrosis.
• Uses: EW-7197 is a highly potent, selective, and orally bioavailable TGF-β I receptor ALK4/ALK5 inhibitor.

Technology Process of EW-7197

There total 6 articles about EW-7197 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:

C22H16FN7 → N-((4-([1,2,4]triazolo[1,5-a]pyridine-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline (1352608-82-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2014.03.022

Reference yield:

1-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione (356560-84-4) → N-((4-([1,2,4]triazolo[1,5-a]pyridine-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline (1352608-82-2)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium acetate / methanol; tert-butyl methyl ether; water / 4 h / 20 °C

2: hydrogenchloride / water / 4 h / 70 °C

3: acetic acid / 1,2-dichloro-ethane / 2 h / Reflux; Inert atmosphere

4: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; ammonium acetate; acetic acid; In tetrahydrofuran; methanol; tert-butyl methyl ether; water; 1,2-dichloro-ethane;

DOI:10.1016/j.bmc.2014.03.022

Reference yield:

6-(2-(dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine (1352609-89-2) → N-((4-([1,2,4]triazolo[1,5-a]pyridine-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline (1352608-82-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water / 4 h / 70 °C

2: acetic acid / 1,2-dichloro-ethane / 2 h / Reflux; Inert atmosphere

3: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; acetic acid; In tetrahydrofuran; methanol; water; 1,2-dichloro-ethane;

DOI:10.1016/j.bmc.2014.03.022

upstream raw materials:

1-(6-methylpyridin-2-yl)-2-[1,2,4]triazolo-[1,5-a]pyridin-6-yl-ethanone

1-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione

6-(2-(dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine

4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazole-2-carbaldehyde

Downstream raw materials:

N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline hydrochloride

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