1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE
- Product Name
- 1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE
- CAS No.
- 4506-66-5
- Chemical Name
- 1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE
- Synonyms
- 1,2,4,5-Benzenetetraamine tetrahydrochloride;Benzene-1,2,4,5-tetraamine tetrahydrochloride;Y15;FAK Inhibitor 14;1,2,4,5-TETRAAMINOBENZENE TETRAHYDROCHLORIDE;Y-15;NSC 667249;Y15 ，S5321;FAK inhibitor Y15;Y15, 10 mM in DMSO
- CBNumber
- CB4137959
- Molecular Formula
- C6H11ClN4
- Formula Weight
- 174.63
- MOL File
- 4506-66-5.mol
1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE Property
- Melting point:
- ≥300 °C(lit.)
- storage temp.
- room temp
- solubility
- H2O: soluble20mg/mL, clear
- form
- powder
- color
- , faint purple to dark brown
- Water Solubility
- water: 14mg/mL
DMSO: 50mg/mL - BRN
- 3701344
- Stability:
- Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
- InChI
- InChI=1S/C6H10N4.ClH/c7-3-1-4(8)6(10)2-5(3)9;/h1-2H,7-10H2;1H
- InChIKey
- BZDGCIJWPWHAOF-UHFFFAOYSA-N
- SMILES
- NC1C=C(N)C(N)=CC=1N.Cl
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H225Highly Flammable liquid and vapour
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242Use only non-sparking tools.
P243Take precautionary measures against static discharge.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
P363Wash contaminated clothing before reuse.
P370+P378In case of fire: Use … for extinction.
P403+P235Store in a well-ventilated place. Keep cool.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 305065
- Product name
- 1,2,4,5-Benzenetetramine tetrahydrochloride
- Purity
- technical grade
- Packaging
- 1g
- Price
- $115
- Updated
- 2025/07/31
- Product number
- 305065
- Product name
- 1,2,4,5-Benzenetetramine tetrahydrochloride
- Purity
- technical grade
- Packaging
- 5g
- Price
- $395
- Updated
- 2025/07/31
- Product number
- 14485
- Product name
- FAK Inhibitor 14
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 14485
- Product name
- FAK Inhibitor 14
- Purity
- ≥95%
- Packaging
- 25mg
- Price
- $115
- Updated
- 2024/03/01
- Product number
- SML0837
- Product name
- FAK Inhibitor 14
- Purity
- ≥95% (HPLC)
- Packaging
- 10mg
- Price
- $75.7
- Updated
- 2025/07/31
1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE Chemical Properties,Usage,Production
Description
FAK inhibitor 14 (4506-66-5) is a selective focal adhesion kinase (FAK) inhibitor that displays no significant activity at a range of other kinases including EGFR, PDGFR and IGF-R.1 Prevents FAK autophosphorylation at Y397 (IC50 = 1 μM), promotes cell detachment and inhibits cell adhesion in vitro. FAK inhibitor 14 exhibits antiproliferative activity in a variety of human tumor cell lines in vitro and in breast cancer cells in vivo. Induces regression of pancreatic tumors2 and glioblastoma3. Displays antiangiogenic activity.4
Uses
FAK Inhibitor 14 directly blocks phosphorylation of focal adhesion kinase (FAK) in a dose- and time-dependent manner and has also shown breast tumor regression in vivo. It has been suggested that targeting the Y397 site of FAK with FAK Inhibitor 14 can be effectively used in cancer therapy.
Uses
FAK Inhibitor 14 has been used in the metastasis assay. It is also used to study its effect on bone morphogenetic protein 7 (BMP-7)-induced cell crawling and adhesion.
General Description
A cell-permeable tetraamine compound that is identified from a computer-aided molecular docking screening based on Fak Y397 interaction and is shown to inhibit FAK (Cat. No. 324876) autophosphorylation as well as its kinase activity toward paxillin phosphorylation both in cell-free kinase assays (IC50<1 μM) and in BT474 breast cancer cultures, while exhibiting little activity against Pyk2 (Cat. No. 662067) autophosphorylation or the kinase activity of c-Raf, c-Src, EGFR, VEGFR-3, IGF-1, Met, PDGFR-α, Pyk2, and PI 3-K (p110δ/p85α). Reported to inhibit BT474 proliferation both in cultures in vitro (IC50 ~10 μM) and in mice in vivo (~25% of no treatment controls on day 23; 30 mg/kg via 5 i.p/wk).
Biological Activity
Selective focal adhesion kinase (FAK) inhibitor that displays no significant activity at a range of other kinases including EGFR, PDGFR and IGF-RI. Prevents FAK autophosphorylation at Y397 (IC 50 = 1 μ M), promotes cell detachment and inhibits cell adhesion in vitro . Exhibits antiproliferative activity in a variety of human tumor cell lines in vitro and in breast cancer cells in vivo .
Biochem/physiol Actions
1,2,4,5-Benzenetetraamine tetrahydrochloride (FAK Inhibitor 14; Y15) is a cell-permeable, selective focal adhesion kinase (FAK) inhibitor. Focal adhesion kinase (FAK) is essential in regulating integrin signaling pathways responsible for cell survival, cell proliferation and motility. Phosphorylation of FAK tyrosine 397 (Y397) forms a high affinity binding site for the SH2 domain of the Src family kinases and PI3 kinase. FAK is overexpressed in a number of human tumors. 1,2,4,5-Benzenetetraamine tetrahydrochloride (FAK Inhibitor 14, Y15) blocks phosphorylation of Y397-FAK, which results in neuroblastoma cell detachment and apoptosis.
Synthesis
4987-96-6
4506-66-5
1. Treat 4,6-dinitro-1,3-phenylenediamine in an inert atmosphere to prevent oxidation. To a 2-gallon autoclave was added 480 g of 1,5-diamino-2,4-dinitrobenzene, 5.5 g of tin powder (T1 grade), and 9.6 g of Degussa F101 Pt/C catalyst. After sealing the autoclave, the system was purged with nitrogen and 2000 mL of ethanol treated with nitrogen injection was added. 2. The autoclave was heated to 70 °C and pressurized with hydrogen to 300 psi. the reaction was held at 80.5 °C and 300 psi for 2 h. 3. After the reaction was complete, the mixture in the autoclave was pushed through a solid filter into a precipitation vessel. After cooling to 15 °C, 1,2,4,5-benzenetetramine tetrahydrochloride was precipitated by the addition of 1400 mL of 12.1 M HCl. 4. The precipitated solid was collected and washed sequentially with 12.1 M HCl and ethanol. The product was partially dried over a filter at 40 °C by nitrogen and vacuum. Eventually 557.3 g of 1,2,4,5-benzenetetramine tetrahydrochloride was obtained in 81% yield.5. For further purification, 1,2,4,5-benzenetetramine tetrahydrochloride can be crystallized from an aqueous solution by means of concentrated hydrochloric acid.
storage
Desiccate at RT
References
[1] VITA M. GOLUBOVSKAYA. A Small Molecule Inhibitor, 1,2,4,5-Benzenetetraamine Tetrahydrochloride, Targeting the Y397 Site of Focal Adhesion Kinase Decreases Tumor Growth[J]. Journal of Medicinal Chemistry, 2008, 51 23: 7405-7416. DOI:10.1021/jm800483v
[2] STEVEN N HOCHWALD. A novel small molecule inhibitor of FAK decreases growth of human pancreatic cancer.[J]. Cell Cycle, 2009, 8 15: 2435-2443. DOI:10.4161/cc.8.15.9145
[3] VITA M GOLUBOVSKAYA. Pharmacologic blockade of FAK autophosphorylation decreases human glioblastoma tumor growth and synergizes with temozolomide.[J]. Molecular Cancer Therapeutics, 2013, 12 2: 162-172. DOI:10.1158/1535-7163.mct-12-0701
[4] MIGUEL A. CABRITA . Focal adhesion kinase inhibitors are potent anti-angiogenic agents[J]. Molecular Oncology, 2011, 5 6: Pages 517-526. DOI:10.1016/j.molonc.2011.10.004
1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE Preparation Products And Raw materials
Raw materials
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View Lastest Price from 1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE manufacturers
- Product
- 1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE 4506-66-5
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%min
- Supply Ability
- 20tons
- Release date
- 2025-09-09
- Product
- Benzol-1,2,4,5-tetramintetrahydrochlorid 4506-66-5
- Price
- US $2.00-5.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-07-08
- Product
- 1,2,4,5-BENZENETETRAMINE TETRAHYDROCHLORIDE 4506-66-5
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-11-15