55778-02-4

Basic information

• Product Name: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine
• Synonyms: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine;WZ 811;N,N'-Di-2-pyridinyl-1,4-benzenedimethanamine;N,N'-(1,4-phenylenebis(methylene))bis(pyridin-2-amine);1,4-Benzenedimethanamine, N1,N4-di-2-pyridinyl-;N1,N4-di-2-pyridinyl-1,4-benzenedimethanamine WZ811;WZ 811 N,N'-Di-2-pyridinyl-1,4-benzenedimethanamine;WZ 811, >=98%
• CAS NO: 55778-02-4
• Molecular Formula: C18H18N4
• Molecular Weight: 290.36232
• EINECS: 200-256-5
• Product Categories: Inhibitors
• Mol File: 55778-02-4.mol

Chemical Properties

• Melting Point: 192-194℃ (methanol )
• Boiling Point: 493.2±35.0 °C(Predicted)
• Appearance: white to tan/
• Density: 1.229±0.06 g/cm3(Predicted)
• Storage Temp.: Store at -20°C
• Solubility: DMSO: ≥7mg/mL
• PKA: 6.55±0.10(Predicted)
• CAS DataBase Reference: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine(55778-02-4)
• EPA Substance Registry System: N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine(55778-02-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 55778-02-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine is used as an inhibitor for the chemokine receptor CXCR4 for its ability to block the binding of SDF-1 peptide mimic to CXCR4 (EC50 = 0.3 nM). This inhibition 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), making it a potential therapeutic agent for cancer treatment.
Used in HIV Treatment:
N1,N4-Di-2-pyridinyl-1,4-benzenedimethanamine is used as an inhibitor for CXCR4 on CD4+ T-cells, as it prevents the use of this receptor by CXCR4-selective HIV forms as a gateway for T-cell infection. This application could potentially contribute to the development of new strategies for HIV treatment and prevention.
The effectiveness of WZ811 in animals and its potential applications in other industries remain to be further investigated and elucidated.

references

[1] zhan w, liang z, zhu a, et al. discovery of small molecule cxcr4 antagonists. journal of medicinal chemistry, 2007, 50(23): 5655-5664.[2] choi w t, duggineni s, xu y, et al. drug discovery research targeting the cxc chemokine receptor 4 (cxcr4). journal of medicinal chemistry, 2011, 55(3): 977-994.

Upstream product

• 504-29-0 2-aminopyridine 
• 589-29-7 p-xylylene glycol 
• 46224-49-1 (pyridin-1-iumyl)[(pyridin-2-yl)aminide] 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 623-27-8 terephthalaldehyde, 

Relevant articles and documents

Pyridinium N-(2′-azinyl)aminides: Regioselective synthesis of N-(2-pyridyl) substituted polyamines

The regioselective alkylation of pyridinium-N-(2′-pyridyl)aminide with alkyl dihalides under mild conditions, followed by N-N bond reduction of the corresponding bis-salts, allowed an easy preparation of N,N′-bis(2-pyridyl)diamines. The same methodology h

N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: Scope and mechanistic considerations

Copper(II) acetate is a versatile, cheap and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, phosphinamides, sulfonamides, and phosphazenes, using in all cases primary alcohols as initial source of the electrophiles, through a hydrogen autotransfer process. In the case of sulfonamides, the monoalkylation process followed by a naphthalene-catalyzed reductive deprotection gives primary amines, which is an indirect alternative to the direct monoalkylation of ammonia. A study of the reaction using deuterium labelled reagents was performed, indicating that the dehydrogenation and hydrogenation steps do not take placed on the same copper-atom coordination sphere, with the condensation step occurring out of the dehydrogenating catalytic species.

Discovery of small molecule CXCR4 antagonists

In light of a proposed molecular mechanism for the C-X-C chemokine receptor type 4 (CXCR4) antagonist 1 (AMD3100), a template with the general structure 2 was designed, and 15 was identified as a lead by means of an affinity binding assay against the liga

CXCR4 ANTAGONISTS FOR THE TREATMENT OF HIV INFECTION

The invention provides compounds, pharmaceutical compositions and methods of use of certain compounds that are antagonists of the chemokine CXCR4 receptor, and in particular to inhibit viral entry of certain viruses. Certain compounds in particular can reduce entry of immunodeficiency virus (HIV) into a cell while not reducing the capacity of stem cells to proliferate, and therefore can be useful for long term treatment regimes. The compounds are useful in particular in the treatment or prevention of HIV infections.