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:

• General Description: NLG919 is an IDO1 inhibitor whose stereochemistry significantly influences its pharmacological activity, with the S configuration at the C5 position being essential for optimal inhibitory effects, while the stereochemistry at the C2’ position plays a lesser role. NLG919's optically pure stereoisomers were successfully resolved and characterized, confirming the importance of chiral specificity for its biological function.

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:

1-cyclohexyl-2-(5H-imidazo[5,1-α]isoindol-5-yl)ethyl acetate

1-cyclohexyl-2-(5H-imidazo[5,1-α]isoindol-5-yl)ethyl phenylcarbamate

1-cyclohexyl-2-[5H-imidazo[4,3-a]isoindol-5-yl]ethan-1-amine

(E)-5-(2-cyclohexylvinyl)-5H-imidazo[5,1-α]isoindole

Refernces

Chiral resolution, absolute configuration determination, and stereo-activity relationship study of IDO1 inhibitor NLG919

10.1016/j.tet.2018.05.005

The research focuses on the development of an effective method to prepare optically pure stereoisomers of the IDO1 inhibitor NLG919. The study involves the chiral resolution of the racemic intermediate 2 using di-p-toluoyl-L-tartaric acid (L-7) in a dichloromethane and n-pentane solvent system. The absolute configurations of the stereoisomers were determined through electronic circular dichroism (ECD) spectra, quantum-chemical calculations, and transition metal methods. The pharmacological evaluation revealed that the S configuration at the C5 position is crucial for the IDO1 inhibitory activity, while the stereochemistry at the C2’ position has less impact.

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