| Identification | Back Directory | [Name]
6-AMINO-4-(4-PHENOXYPHENYLETHYLAMINO)QUINAZOLINE | [CAS]
545380-34-5 | [Synonyms]
QNZ
EVP4593
EVP-4593
EVP 4593
QNZ (EVP4593)
NF-κB Activation Inhibitor
N4-(4-Phenoxyphenethyl)quinazoline-4,6-diamine
N4-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediaMine
4-N-[2-(4-Phenoxyphenyl)ethyl]quinazoline-4,6-diamine
4,6-Quinazolinediamine, N4-[2-(4-phenoxyphenyl)ethyl]- | [Molecular Formula]
C22H20N4O | [MDL Number]
MFCD06411436 | [MOL File]
545380-34-5.mol | [Molecular Weight]
356.42 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
169-175°C | [storage temp. ]
Refrigerator, Under Inert Atmosphere | [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. | [InChI]
1S/C22H20N4O/c23-17-8-11-21-20(14-17)22(26-15-25-21)24-13-12-16-6-9-19(10-7-16)27-18-4-2-1-3-5-18/h1-11,14-15H,12-13,23H2,(H,24,25,26) | [InChIKey]
IBAKVEUZKHOWNG-UHFFFAOYSA-N | [SMILES]
NC1=CC(C(NCCC2=CC=C(OC3=CC=CC=C3)C=C2)=NC=N4)=C4C=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
QNZ is a novel inhibitor of NFkB which displays potent inhibitory effects on both NFKB transcriptional activation (IC50=11nM) and TNF-a production (IC50=7nM). It dose-dependently inhibited carragenin-induced edema formation in the rat paw model (1m | [Uses]
QNZ is a novel inhibitor of NFkB which displays potent inhibitory effects on both NFKB transcriptional activation (IC50=11nM) and TNF-α production (IC50=7nM). It dose-dependently inhibited carragenin-induced edema formation in the rat paw model (1mg/Kg). A useful tool to explore the role of NFkB in cellular signaling pathways. | [Uses]
QNZ is an inhibitor of NF-κB activation with IC50 of 11 nM. | [Description]
QNZ (545380-34-5) was originally described as a potent inhibitor of NF-κB activation (IC50?= 11 nM) and TNF-α?production (IC50?= 7 nM).1,2?It indirectly inhibits the NF-κB pathway via inhibition of store-operated calcium entry (SOC) and displayed neuroprotective effects in transgenic fly and mouse models of Huntington’s disease.3,4?Its target has been postulated to be heteromeric calcium channels containing TRPC1 as one of the subunits.4?QNZ reduced synaptic neuronal SOC and rescued dendritic spine loss in YAC128 striatal medium spiny neurons.5?QNZ has also been identified as a potent (IC50?= 25 nM complex 1 from?Y.lipolytica; IC50?= 14 nM complex 1 from?Bos Taurus?heart mitochondria) and selective inhibitor of mitochondrial complex I.6?QNZ?decreased PSEN1ΔE9-mediated nSOCE upregulation and rescued mushroom spines in PSEN1ΔE9-expressing neurons, which are linked to familial Alzheimer’s disease.7 | [target]
NF-κB | [IC 50]
NF-κB: 11 nM (IC50, in human Jurkat cells transfected with pNFκB-Luc) | [References]
1) Tobe?et al. (2003),?Discovery of quinazolines as a novel structural class of potent inhibitors of NF-kappa B activation; Bioorg. Med. Chem. Lett,?11?383
2) Tobe?et al.?(2003),?A novel structural class of potent inhibitors of NF-kB activation: structure-activity relationships and biological effects of 6-aminoquinazoline derivatives; Bioorg. Med. Chem. Lett,?11?3869
3) Choi?et al.?(2006),?Nuclear factor-kappaB activated by capacitive Ca2+ entry enhances muscarinic receptor-mediated soluble amyloid precursor protein (sAPPalpha) release in SH-SY5Y cells; J. Biol. Chem.,?281?12722
4) Wu?et al.?(2011),?Neuronal Store-Operated Calcium Entry Pathway as a Novel Therapeutic Target for Huntington’s Disease Treatment; Chem. Biol.,?18?777
5) Wu?et al. (2016),?Enhanced Store-Operated Calcium Entry Leads to Striatal Synaptic Loss in a Huntington’s Disease Mouse Model; J. Neurosci.,?36?125
6) Krishnathas?et al. (2017),?Identification of 4-N-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine as a novel, highly potent and specific inhibitor of mitochondrial complex I; Medchemcomm.?8?657
7) Chernyuk?et al. (2019),?Antagonist of neuronal store-operated calcium entry exerts beneficial effects in neurons expressing PSEN1?E9 mutant linked to familial Alzheimer disease;?Neuroscience,?410?118 |
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