CAS Number545380-34-5
SynonymsN-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediamine; 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline; N-[2-(4-Phenoxyphenyl)ethyl]quinazoline-4,6-diamine; QNZ; N4-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediamine; EVP4593
Molecular FormulaC22H20N4O
Molecular Weight356.42
Purity≥98 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point602.0±55.0 °C at 760 mmHg
Melting Point169-175ºC
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 545380-34-5 |
| Catalog No. | 2A-9079935 |
| Chinese Name | QNZ (EVP4593) |
| Synonyms | N-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediamine; 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline; N-[2-(4-Phenoxyphenyl)ethyl]quinazoline-4,6-diamine; QNZ; N4-[2-(4-Phenoxyphenyl)ethyl]-4,6-quinazolinediamine; EVP4593 |
| Molecular Formula | C22H20N4O |
| Molecular Weight | 356.42 |
| Purity | ≥98 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 602.0±55.0 °C at 760 mmHg |
| Melting Point | 169-175ºC |
| Appearance | solid |
| Water Solubility | DMSO: soluble15mg/mL, clear |
| Storage Condition | Refrigerator, Under Inert Atmosphere |
| Application | QNZ strongly inhibits NF-κB transcriptional activation and TNF-α production with IC50 of 11 and 7 nM, respectively. QNZ is a neuroprotective inhibitor of store-operated calcium channels (SOC). |
| HTC | 2933990090 |
| PubChem ID | 810701 |
| MDL Number | MFCD06411436 |
| SMILES | N(CCc3ccc(cc3)Oc4ccccc4)c1ncnc2c1cc(cc2)N |
| 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) |
| InChI Key | IBAKVEUZKHOWNG-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/79935_1_545380_34_5.pdf |
| Bioactivity | QNZ shows strong inhibitory effects on NF-κB transcriptional activation and TNF-α production with IC50s of 11 and 7 nM, respectively. EVP4593 is a neuroprotective inhibitor of SOC channel. Related Catalog Signaling Pathways >> NF-κB >> NF-κB Signaling Pathways >> Apoptosis >> TNF Receptor Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease Target NF-κB:11 nM (IC50, in human Jurkat cells transfected with pNFκB-Luc) TNF-α:7 nM (IC50, in murine splenocytes stimulated with LPS) In Vitro QNZ (Compound 11q) has a suppressing effect of the NF-κB mediated-inflammatory response. QNZ inhibits edema formation dose-dependently[1]. QNZ (EVP4593) reduces the number of lysosomes/autophagosomes and store-operated channel (SOC) currents in Huntington's disease (HD). Normalization of calcium transport within neurons in response to QNZ is expect to reduce pathology manifestation. A number of lysosomes/autophagosomes are evaluated in HD and WT neurons treated with QNZ using transmission electron microscopy (TEM). Incubation with QNZ reduces the number of lysosomes/autophagosomes in HD GABAergic medium spiny (GABA MS)-like neurons (GMSLNs) by almost two-fold (from 0.41±0.04 to 0.23±0.04; p<0.05), while WT neurons are not affected. This observation is confirmed by examining lysosome content by flow cytometry (FC) analysis. The median fluorescence intensity is reduced by 34±6 % in HD GMSLNs upon QNZ treatment (p<0.05)[2]. Cell Assay iPSHD22 cells are cultured in K-4 medium in a 96-well black plates with clear flat bottom. Next, cells are treated with chemical compounds (e.g., QNZ 100 nM) for 24 h prior to analysis. Fluorescent assay MultiTox-Fluor Multiplex Cytotoxicity Assay is used to measure simultaneously the relative number of live (viability) and dead (cytotoxicity) cells in each well. Fluorescence is detected by DTX 880 Multimode Microplate Reader. To evaluate the level of cell death (LoCD), the following equation is employed: ([cytotoxicity in a well with cells]-[cytotoxicity in a well without cells])/([viability in a well with cells]-[viability in a well without cells])[2]. References [1]. Tobe M, et al. Discovery of quinazolines as a novel structural class of potent inhibitors of NF-kappa B activation. [2]. Nekrasov ED, et al. Manifestation of Huntington's disease pathology in human induced pluripotent stem cell-derived neurons. Mol Neurodegener. 2016 Apr 14;11:27. [3]. Wu J, et al. Enhanced Store-Operated Calcium Entry Leads to Striatal Synaptic Loss in a Huntington's Disease Mouse Model. J Neurosci. 2016 Jan 6;36(1):125-41. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 602.0±55.0 °C at 760 mmHg Melting Point 169-175ºC Molecular Formula C22H20N4O Molecular Weight 356.420 Flash Point 317.9±31.5 °C Exact Mass 356.163696 PSA 73.06000 LogP 4.57 Vapour Pressure 0.0±1.7 mmHg at 25°C Index of Refraction 1.714 InChIKey IBAKVEUZKHOWNG-UHFFFAOYSA-N SMILES Nc1ccc2ncnc(NCCc3ccc(Oc4ccccc4)cc3)c2c1 Storage condition Refrigerator, Under Inert Atmosphere Water Solubility DMSO: soluble15mg/mL, clear |
| Use of | QNZ shows strong inhibitory effects on NF-κB transcriptional activation and TNF-α production with IC50s of 11 and 7 nM, respectively. EVP4593 is a neuroprotective inhibitor of SOC channel. Properties Name 4-N-[2-(4-phenoxyphenyl)ethyl]quinazoline-4,6-diamine Synonym More Synonyms QNZ (EVP4593) Biological Activity Description QNZ shows strong inhibitory effects on NF-κB transcriptional activation and TNF-α production with IC50s of 11 and 7 nM, respectively. EVP4593 is a neuroprotective inhibitor of SOC channel. Related Catalog Signaling Pathways >> NF-κB >> NF-κB Signaling Pathways >> Apoptosis >> TNF Receptor Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease NF-κB:11 nM (IC50, in human Jurkat cells transfected with pNFκB-Luc) TNF-α:7 nM (IC50, in murine splenocytes stimulated with LPS) References [1]. Tobe M, et al. Discovery of quinazolines as a novel structural class of potent inhibitors of NF-kappa B activation. [2]. Nekrasov ED, et al. Manifestation of Huntington's disease pathology in human induced pluripotent stem cell-derived neurons. Mol Neurodegener. 2016 Apr 14;11:27. [3]. Wu J, et al. Enhanced Store-Operated Calcium Entry Leads to Striatal Synaptic Loss in a Huntington's Disease Mouse Model. J Neurosci. 2016 Jan 6;36(1):125-41. Chemical & Physical Properties Molecular Formula C22H20N4O Exact Mass 356.163696 PSA 73.06000 Index of Refraction 1.714 InChIKey IBAKVEUZKHOWNG-UHFFFAOYSA-N Storage condition Refrigerator, Under Inert Atmosphere |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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