N-[[4-[(pyridin-2-ylamino)methyl]phenyl]methyl]pyridin-2-amine

Base Information

• Chemical Name: N-[[4-[(pyridin-2-ylamino)methyl]phenyl]methyl]pyridin-2-amine
• CAS No.: 55778-02-4
• Molecular Formula: C18H18N4
• Molecular Weight: 290.36
• European Community (EC) Number: 694-750-1
• ChEMBL ID: CHEMBL237830
• DSSTox Substance ID: DTXSID10468697
• Nikkaji Number: J1.819.277B
• Wikidata: Q82296039
• Mol file: 55778-02-4.mol

Synonyms:N,N'-di-2-pyridinyl-1,4-benzenedimethanamine;WZ 811;WZ-811;WZ811 cpd

Chemical Property of N-[[4-[(pyridin-2-ylamino)methyl]phenyl]methyl]pyridin-2-amine

Chemical Property:

• Melting Point: 192-194℃ (methanol )
• Boiling Point: 493.2±35.0 °C(Predicted)
• PKA: 6.55±0.10(Predicted)
• PSA: 49.84000
• Density: 1.229±0.06 g/cm3(Predicted)
• LogP: 3.84680
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥7mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 290.153146591
• Heavy Atom Count: 22
• Complexity: 272

Purity/Quality:

98% min ^*data from raw suppliers

WZ 811 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)NCC2=CC=C(C=C2)CNC3=CC=CC=N3
• Description: The CXC chemokine receptor-4 (CXCR4) is a G protein-coupled receptor that is specific for stromal cell-derived factor-1 (SDF-1/ CXCL12). Activation of CXCR4 promotes homing of hematopoietic stem cells, chemotaxis and quiescence of lymphocytes, and growth and metastasis of certain cancer cell types. Moreover, CXCR4 on CD4+ T-cells is used by CXCR4-selective HIV forms as a gateway for T-cell infection. WZ811 is a potent inhibitor of binding of an SDF-1 peptide mimic to CXCR4 (EC50 = 0.3 nM). It prevents SDF-1/CXCL12-mediated modulation of cAMP (EC50 = 1.2 nM) in cells and blocks SDF-1-induced Matrigel? invasion by MDA-MB-231 human breast adenocarcinoma cells (EC50 = 5.2 nM). The effectiveness of WZ811 in animals remains to be elucidated.
• Uses: N1,N4-di-2-Pyridinyl-1,4-benzenedimethanamine acts as an inhibitor for the chemokine receptor CXCR4.

Technology Process of N-[[4-[(pyridin-2-ylamino)methyl]phenyl]methyl]pyridin-2-amine

There total 6 articles about N-[[4-[(pyridin-2-ylamino)methyl]phenyl]methyl]pyridin-2-amine 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: 56.0%

2-aminopyridine (504-29-0) + terephthalaldehyde, (623-27-8) → WZ811 (55778-02-4)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; for 5h;

DOI:10.1021/jm070679i

Reference yield: 55.0%

2-aminopyridine (504-29-0) + p-xylylene glycol (589-29-7) → WZ811 (55778-02-4)

Guidance literature:

With potassium tert-butylate; copper diacetate; In 1,4-dioxane; at 130 ℃; for 96h; Inert atmosphere;

DOI:10.1016/j.tet.2011.02.075

Reference yield: 55.0%

1-{[4-(pyridin-1-ium-pyridin-2-ylaminomethyl)benzyl]pyridin-2-ylamino}pyridinium dibromide → WZ811 (55778-02-4)

Guidance literature:

With formic acid; triethylamine; platinum on activated charcoal; In acetonitrile; for 4h; Heating;

DOI:10.1016/S0040-4020(02)00901-8

upstream raw materials:

2-aminopyridine

terephthalaldehyde,

1,4-bis(bromomethyl)benzene

(pyridin-1-iumyl)[(pyridin-2-yl)aminide]

Refernces

• 1、 Martínez-Asencio, Ana,Ramón, Diego J.,Yus, Miguel. "N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: Scope and mechanistic considerations". experimental part. p. 3140 - 3149. Retrieved 2011/05/06.
• 2、 -. "CXCR4 ANTAGONISTS FOR THE TREATMENT OF HIV INFECTION". Page/Page column 61. . Retrieved 2008/06/13.