6-Amino-4-(4-phenoxyphenylethylamino)quinazoline

Base Information

• Chemical Name: 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline
• CAS No.: 545380-34-5
• Molecular Formula: C22H20N4O
• Molecular Weight: 356.42
• Hs Code.: 2933990090
• Mol file: 545380-34-5.mol

Synonyms:4,6-quinazolinediamine, N⁴-[2-(4-phenoxyphenyl)ethyl]-;

Chemical Property of 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.9E-14mmHg at 25°C
• Melting Point: 169-175°C
• Refractive Index: 1.713
• Boiling Point: 602 °C at 760 mmHg
• Flash Point: 317.9 °C
• PSA: 73.06000
• Density: 1.275 g/cm³
• LogP: 5.31310
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO: soluble15mg/mL, clear

Purity/Quality:

99% ^*data from raw suppliers

6-Amino-4-(4-phenoxyphenylethylamino)quinazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• 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 QNZ is an inhibitor of NF-κB activation with IC50 of 11 nM.

Technology Process of 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline

There total 9 articles about 6-Amino-4-(4-phenoxyphenylethylamino)quinazoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.3%

6-nitro-4-(4-phenoxyphenylethylamino)quinazoline (545380-35-6) → NF-kB Activation Inhibitor (545380-34-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 5h;

Reference yield:

4-chloro-6-nitro-quinazoline (19815-16-8) → NF-kB Activation Inhibitor (545380-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 403 mg / Et₃N / propan-2-ol / 1 h / 20 °C

2: 77 percent / Fe / ethanol; H₂O; acetic acid / 0.5 h / Heating

With iron; triethylamine; In ethanol; water; acetic acid; isopropyl alcohol;

DOI:10.1016/S0968-0896(02)00440-6

Reference yield:

6-nitroquinazolone (6943-17-5) → NF-kB Activation Inhibitor (545380-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂; DMF / 3 h / Heating

2: 403 mg / Et₃N / propan-2-ol / 1 h / 20 °C

3: 77 percent / Fe / ethanol; H₂O; acetic acid / 0.5 h / Heating

With thionyl chloride; iron; triethylamine; N,N-dimethyl-formamide; In ethanol; water; acetic acid; isopropyl alcohol;

DOI:10.1016/S0968-0896(02)00440-6

upstream raw materials:

6-nitro-4-(4-phenoxyphenylethylamino)quinazoline

4-chloro-6-nitro-quinazoline

6-nitroquinazolone

2-amino-5-nitrobenzamide

Refernces

• 1、 Shi, Hailong,Li, Yan,Ren, Xiaorong,Zhang, Yaohong,Yang, Zhen,Qi, Chenze. "A novel quinazoline-based analog induces G2/M cell cycle arrest and apoptosis in human A549 lung cancer cells via a ROS-dependent mechanism". . p. 314 - 320. Retrieved 2017/04/04.