1402838-89-4

Basic information

• Product Name: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone
• Synonyms: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone
• CAS NO: 1402838-89-4
• Molecular Formula: C₁₈H₂₀N₂O
• Molecular Weight: 280.3642
• EINECS: -0
• Mol File: 1402838-89-4.mol

Chemical Properties

• Boiling Point: 521.5±33.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 6.12±0.40(Predicted)
• CAS DataBase Reference: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone(1402838-89-4)
• EPA Substance Registry System: 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone(1402838-89-4)

Safety Data

• Hazardous Substances Data: 1402838-89-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone is used as a potential pharmaceutical compound for its unique structure and functional groups. The presence of the imidazoisoindolyl group may contribute to its biological activity, warranting further research into its applications in drug development.
Used in Organic Synthesis:
In the field of organic synthesis, 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone serves as a valuable intermediate or building block for the creation of more complex molecules. Its specific structural features and functional groups can be leveraged to synthesize a variety of organic compounds with diverse applications.

Upstream product

• 40138-16-7 2-formylbenzene boronic acid 
• 96797-15-8 N-trityl-4⁽⁵⁾-iodoimidazole 
• 1402838-08-7 2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde 
• 58009-66-8 dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 80783-98-8 N-methoxy-N-methylcyclohexanecarboxamide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 823-76-7 Cyclohexyl methyl ketone 
• 3289-28-9 ethyl cyclohexanecarboxylate 

Downstream Products

• 1402836-82-1 1-cyclohexyl-2-[5H-imidazo[4,3-a]isoindol-5-yl]ethan-1-amine 
• 1402837-18-6 (E)-5-(2-cyclohexylvinyl)-5H-imidazo[5,1-α]isoindole 
• 1402836-58-1 rac-5-(2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole 
• 1402837-22-2 (R)-5-((S)-2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole 
• 1402837-21-1 (R)-5-((R)-2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole 
• 1402837-23-3 (S)-5-((S)-2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole 
• 1402837-24-4 (S)-5-((R)-2-hydroxyl(cyclohexylethyl))-5H-imidazo[5,1-a]isoindole 
• 1402836-79-6 (Z)-1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one oxime 

Relevant articles and documents

Discovery of clinical candidate (1 R,4 r)-4-((R)-2-((S)-6-Fluoro-5 H-imidazo[5,1-A[isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a potent and selective inhibitor of indoleamine 2,3-dioxygenase 1

A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.

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

NLG919 (1) with two chiral carbon atoms on its chemical structure is a potent indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor. We developed an effective way to prepare all stereoisomers of 1, the key step being the chiral resolution of racemic intermediate 2. The optimal resolution solvent system was identified as dichloromethane and n-pentane or petroleum ether. Using (?)-di-p-toluoyl-D-tartaric acid as resolution reagent, optical pure (R)-2 (e.e. > 99%, yield = 70%) was obtained. The mechanism of chiral resolution was clarified through single-crystal X-ray diffraction of the diastereomeric salt. The absolute configurations of four stereoisomers of 1 were established through electronic circular dichroism spectra, quantum chemical calculation and transition metal method. Their IDO1 inhibitory activity was assessed by pharmacological experiments in vitro and in mouse, demonstrating that S configuration of C5 played an important role on the inhibition of IDO1, while the stereochemistry on C2′ exerted little effect on the IDO1 inhibitory activity in mouse.

Discovery of imidazoleisoindole derivatives as potent IDO1 inhibitors: Design, synthesis, biological evaluation and computational studies

Indoleamine-2,3-dioxygenase-1 (IDO1) is an attractive target for cancer immunotherapy. Herein, a series of novel imidazoleisoindole derivatives were prepared and evaluated for their ability to inhibit IDO1. Among these, derivative 11r was the most active compound with nanomolar potency in the Hela cell-based assay, while showed negligible cellular toxicity. UV-visible spectra study demonstrated that compounds 11p and 11r bound to IDO1 and coordinated with the heme iron. Furthermore, they could significantly promote T cell proliferation, increase IFN-γ production, and reduce the numbers of Foxp3+ regulatory T cells. Finally, induced fit docking (IFD) and quantum mechanics/molecular mechanics (QM/MM) calculation were performed to understand the interactions of these compounds to IDO1 protein, which provided a comprehensive guide for further structural modification and optimization.

Imidazo isoindole IDO1 inhibitor as well as preparation method and application thereof

The invention belongs to the field of medicine, and particularly relates to an imidazo isoindole IDO1 compound with structural characteristics of the formula (I) shown in the description as well as a three-dimensional isomer or a pharmaceutically acceptable salt thereof, a preparation method thereof and application thereof as an indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor. An experiment result shows that the compound of the invention has a significant inhibition effect for the activity of IDO1, can effectively promote the proliferation of cells T, prevents initial cells T from being differentiated into adjustable cells T, can invert IDO1 mediating immunosuppression, can be used for treating relevant diseases with pathological features of an IDO1 mediating kynurenine metabolic way including cancers, virus infection, neurodegenerative diseases, cataracts, organ transplant rejection, depression, autoimmune diseases and the like.

COMPOUNDS FOR THE INHIBITION OF INDOLEAMINE-2,3-DIOXYGENASE

The present invention relates to compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of IDO, and for the treatment of IDO-related disorders.

A deuterated of the IDO inhibitor and its preparation and use (by machine translation)

The invention provides a deuterated of the IDO inhibitor and its preparation and use, as shown in formula I provide compound or its crystalline form, a pharmaceutically acceptable salt, hydrate or solvate. The preparation of the compound or its crystalline form, a pharmaceutically acceptable salt, hydrate or solvate, can be regarded as the IDO inhibitor, can be used for the treatment of IDO related diseases, in particular cancer, viral infection, depression, neurodegenerative disease, trauma, age-related cataract, organ transplant rejection and autoimmune diseases. (by machine translation)

FUSED IMIDAZOLE DERIVATIVES USEFUL AS IDO INHIBITORS

Presently provided are IDO inhibitors and pharmaceutical compositions thereof, useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated inimunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.