| Identification | Back Directory | [Name]
NLG919 | [CAS]
1402836-58-1 | [Synonyms]
CS-820
NLG919
GDC0919
GDC-0919
GDC 0919
NLG919, >=98%
NLG919;NLG-919
IDO inhibitor 7
NLG-919 analogue
NLG919;NAVOXIMOD
NLG919 USP/EP/BP
NLG919 (GDC-0919)
NLG919(GDC-0919,Navoximod)
5H-Imidazo[5,1-a]isoindole-5-ethanol, α-cyclohexyl-
alpha-Cyclohexyl-5H-imidazo[5,1-a]isoindole-5-ethanol
1-CYCLOHEXYL-2-(5H-IMIDAZO[5,1-A]ISOINDOL-5-YL)ETHANOL
NLG-919; NLG 919; IDO INHIBITOR;GDC-0919;GDC 0919;GDC0919
1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol
5-(2-Cyclohexyl-2-hydroxyethyl)-5H-imidazo[5,1-a]isoindole
1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanol NLG919
NLG919 1-CYCLOHEXYL-2-(5H-IMIDAZO[5,1-A]ISOINDOL-5-YL)ETHANOL | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C18H22N2O | [MDL Number]
MFCD26142661 | [MOL File]
1402836-58-1.mol | [Molecular Weight]
282.38 |
| Chemical Properties | Back Directory | [Melting point ]
143 - 146°C | [Boiling point ]
524.6±33.0 °C(Predicted) | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (up to 15 mg/ml) | [form ]
solid | [pka]
14.85±0.20(Predicted) | [color ]
White | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [InChI]
InChI=1S/C18H22N2O/c21-18(13-6-2-1-3-7-13)10-16-14-8-4-5-9-15(14)17-11-19-12-20(16)17/h4-5,8-9,11-13,16,18,21H,1-3,6-7,10H2 | [InChIKey]
YTRRAUACYORZLX-UHFFFAOYSA-N | [SMILES]
C(O)(C1CCCCC1)CC1C2=C(C=CC=C2)C2=CN=CN21 |
| Hazard Information | Back Directory | [Description]
(±)-NLG-919 is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor (Ki = 7 nM; EC50 = 75 nM).1 (±)-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.2 | [Uses]
NLG919 is a potent indoleamine-2,3-dioxygenase (IDO) pathway inhibitor and is suitable for the treatment of immunosuppression associated with cancer. | [Synthesis]
Sodium borohydride (81 mg, 2.14 mmol) was slowly added to a methanol solution (5 mL) containing 1-cyclohexyl-2-[5H-imidazo[4,3-a]isoindol-5-yl]ethan-1-one (300 mg, 1.07 mmol) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 30 min. Subsequently, the reaction was quenched with deionized water (30 mL) and extracted with ethyl acetate (50 mL x 2). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by fast column chromatography using a solvent mixture of dichloromethane and methanol (1% to 6% gradient) as eluent to afford 1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanol as a colorless oil (250 mg, 83% yield). Mass spectrometry result: m/z = 283.1 [M + H]+. | [target]
IDO pathway | [storage]
Store at -20°C | [References]
1) Mautino?et al.?(2013),?NLG919, a novel indolamine-2,3-dioxygenase (IDO)-pathway inhibitor drug candidate for cancer therapy;?Cancer Res.?73?issue 8 supplement?491
2) Li?et al.?(2014),?The indolamine 2,3-dioxygenase pathway controls complement-dependent enhancement of chemo-radiation therapy against murine glioblastoma;?J. Immunother. Cancer?2?21
3) Meng?et al.?(2017),?Combinatorial antitumor effects of indoleamine 2,3-dioxygenase inhibitor NLG919 and paclitaxel in a murine B16-F10 melanoma model;?Int. J. Immunopathol. Pharmacol.?30?215 |
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