1402837-77-7

Basic information

• Product Name: IDO-IN-8
• Synonyms: IDO-IN-8;5H-Imidazo[5,1-a]isoindole-5-ethanol, 6-fluoro-α-(trans-4-hydroxycyclohexyl)-, (αS,5R)-
• CAS NO: 1402837-77-7
• Molecular Formula: C₁₈H₂₁FN₂O₂
• Molecular Weight: 316.3699432
• Mol File: 1402837-77-7.mol

Chemical Properties

• Boiling Point: 555.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• PKA: 14.66±0.20(Predicted)
• CAS DataBase Reference: IDO-IN-8(CAS DataBase Reference)
• NIST Chemistry Reference: IDO-IN-8(1402837-77-7)
• EPA Substance Registry System: IDO-IN-8(1402837-77-7)

Safety Data

• Hazardous Substances Data: 1402837-77-7(Hazardous Substances Data)

Upstream product

• 1402838-09-8 2-fluoro-6-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde 
• 871126-15-7 (3-fluoro-2-formylphenyl)boronic acid 
• 158009-09-7 4-(tert-butyl-dimethyl-silyloxy)cyclohexanecarboxylic acid ethyl ester 

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.

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.