NLG919

Base Information

• Chemical Name: NLG919
• CAS No.: 1402836-58-1
• Molecular Formula: C₁₈H₂₂N₂O
• Molecular Weight: 282.385
• Mol file: 1402836-58-1.mol

Synonyms:rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole

Chemical Property of NLG919

Chemical Property:

• Melting Point: 143 - 146°C
• Boiling Point: 524.6±33.0 °C(Predicted)
• PKA: 14.85±0.20(Predicted)
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 15 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

NLG919 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: (±)-NLG-919 is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor (Ki = 7 nM; EC50 = 75 nM). (±)-NLG-919 inhibits IDO-induced T cell suppression and restores T cell response during allogenic mixed lymphocyte reactions in vitro (ED50s = 80 and 120 nM, respectively). In vivo, (±)-NLG-919 induces a 95% reduction in tumor volume when administered in conjunction with a pmel-1 T cell vaccine. Formulations containing (±)-NLG-919 are under investigation in clinical trials for treatment of glioblastoma, melanoma, pancreatic, and breast cancers.
• Uses: NLG919 is a potent indoleamine-2,3-dioxygenase (IDO) pathway inhibitor and is suitable for the treatment of immunosuppression associated with cancer.

Technology Process of NLG919

There total 10 articles about NLG919 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: 83.0%

rac-1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone (1402838-89-4) → rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole (1402836-58-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

Reference yield: 79.0%

→ rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole (1402836-58-1)

Guidance literature:

Reference yield:

2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde (1402838-08-7) → rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole (1402836-58-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

1.2: 2.5 h / 20 °C

2.1: acetic acid / methanol / 2 h / 90 °C

3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; sodium hydride; acetic acid; In tetrahydrofuran; methanol;

upstream raw materials:

2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde

rac-1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone

2-formylbenzene boronic acid

dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate

Downstream raw materials:

4-(1-cyclohexyl-2-(5H-imidazo[5,1-α]isoindol-5-yl)ethoxy)-4-oxobutanoic acid

Refernces

• 1、 -. "COMPOUNDS FOR THE INHIBITION OF INDOLEAMINE-2,3-DIOXYGENASE". . . Retrieved 2016/04/09.
• 2、 -. "FUSED IMIDAZOLE DERIVATIVES USEFUL AS IDO INHIBITORS". Page/Page column 121. . Retrieved 2012/11/06.