TG4-155

Base Information

• Chemical Name: TG4-155
• CAS No.: 1164462-05-8
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47
• Mol file: 1164462-05-8.mol

Synonyms:(2E)-N-[2-(2-methyl-1H-indol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide

Chemical Property of TG4-155

Chemical Property:

• Boiling Point: 641.3±55.0 °C(Predicted)
• PKA: 14.04±0.46(Predicted)
• Density: 1.14±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 10 mg/ml).

Purity/Quality:

99% ^*data from raw suppliers

TG 4-155 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Prostaglandin E2 (PGE2) evokes distinct responses through four different ‘E prostanoid’ (EP) receptors. EP2 is a G protein-coupled receptor that has diverse roles, including those in cancer, inflammation, and neuroprotection. TG4-155 is a brain penetrant EP2 antagonist (KB = 2.4 nM) that is over 1000-fold less effective at EP4 (KB = 11.4 μM) and a panel of other receptors and channels. It blocks the induced expression of inflammatory markers in microglial cells treated with the selective EP2 agonist butaprost alone or with LPS and IFNγ. TG4-155 significantly reduces neurodegeneration in a mouse model of status epilepticus, induced by pilocarpine . It inhibits proliferation, invasion, and inflammatory cytokine expression in cancer cells treated with butaprost.
• Uses: TG4-155 is a pharmacological agent which reduces neurodegeneration in a mouse model status of epilepticus induced by pilocarpine. Inhibits proliferation, inflammatory cytokine expression in cancer cells.

Technology Process of TG4-155

There total 3 articles about TG4-155 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: 85.0%

(E)-3,4,5-trimethoxy-cinnamic acid (20329-98-0,20329-99-1,90-50-6) + 2-(2-methyl-1H-indol-1-yl)ethan-1-amine (883535-89-5) → (2E)-N-[2-(2-methyl-1H-indol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide (1164462-05-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

2-methyl-1H-indole (95-20-5) → (2E)-N-[2-(2-methyl-1H-indol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide (1164462-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 8 h / 20 °C

With dmap; lithium aluminium tetrahydride; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm5000672

Reference yield:

2-(2-methyl-1H-indol-1-yl)acetonitrile (104894-21-5) → (2E)-N-[2-(2-methyl-1H-indol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide (1164462-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 8 h / 20 °C

With dmap; lithium aluminium tetrahydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm5000672

upstream raw materials:

(E)-3,4,5-trimethoxy-cinnamic acid

2-(2-methyl-1H-indol-1-yl)ethan-1-amine

2-(2-methyl-1H-indol-1-yl)acetonitrile

2-methyl-1H-indole