N2,N4-dibenzylquinazoline-2,4-diamine

Base Information

• Chemical Name: N2,N4-dibenzylquinazoline-2,4-diamine
• CAS No.: 177355-84-9
• Molecular Formula: C₂₂H₂₀N₄
• Molecular Weight: 340.428
• European Community (EC) Number: 695-484-9
• DSSTox Substance ID: DTXSID3040936
• Nikkaji Number: J3.311.374I
• Wikidata: Q72463690
• ChEMBL ID: CHEMBL1624459
• Mol file: 177355-84-9.mol

Synonyms:DBeQ cpd;N2,N4-dibenzylquinazoline-2,4-diamine

Chemical Property of N2,N4-dibenzylquinazoline-2,4-diamine

Chemical Property:

• Melting Point: 149 °C
• Boiling Point: 573.1±52.0 °C(Predicted)
• PKA: 7.78±0.30(Predicted)
• PSA: 56.30000
• Density: 1.259±0.06 g/cm3(Predicted)
• LogP: 3.69780
• Storage Temp.: room temp
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 340.16879665
• Heavy Atom Count: 26
• Complexity: 403

Purity/Quality:

99% ^*data from raw suppliers

DBeQ ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC2=NC(=NC3=CC=CC=C32)NCC4=CC=CC=C4
• Description: DBeQ (177355-84-9) is a potent, selective and reversible inhibitor of the AAA-ATPase p97 (ATPase associated with diverse cellular activities). Ki=3.2 μM. DBeQ blocks ubiquitin-dependent protein clearance pathways. Cell permeable.
• Uses: The ATPase p97 is an ubiquitin-selective chaperone known to play a critical role in the degradation of misfolded membrane and secretory proteins and has been linked to various cellular processes that require unfolding and disassembly of protein complexes. DBeQ is a selective, reversible, and ATP-competitive inhibitor of the ATPase p97 (Ki = 3.2 μM; IC50 = 1.5 μM). It does not exhibit activity when tested against a panel 170 protein kinases at concentrations as high as 15 μM. At 10 μM it blocks endoplasmic reticulum-associated degradation, impairing the autophagy pathway and promoting the activation of caspase-3 and -7 in cancer cells.[Cayman Chemical] HeLa cells were treated with DBeQ and the effects on in vivo ubiquitination and protein dislocation were studied by live cell imaging.

Technology Process of N2,N4-dibenzylquinazoline-2,4-diamine

There total 2 articles about N2,N4-dibenzylquinazoline-2,4-diamine 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: 23.0%

benzylamine (100-46-9) + (4-Amino-chinazolin-2-yl-thio)-essigsaeureethylester (146381-60-4) → N2,N4-dibenzylquinazoline-2,4-diamine (177355-84-9)

Guidance literature:

for 11h; Heating;

DOI:10.1002/prac.19963380144

Reference yield:

[(2-cyanophenyl)aminocarbonylmethyl]chloride (71993-21-0) → N2,N4-dibenzylquinazoline-2,4-diamine (177355-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 2 h / Heating

2: 23 percent / 11 h / Heating

DOI:10.1002/prac.19963380144

upstream raw materials:

benzylamine

(4-Amino-chinazolin-2-yl-thio)-essigsaeureethylester

[(2-cyanophenyl)aminocarbonylmethyl]chloride

Refernces