10537-47-0

Basic information

• Product Name: TYRPHOSTIN A9
• Synonyms: ALPHA-CYANO-(3,5-DI-T-BUTYL-4-HYDROXY)CINNAMONITRILE;TYRPHOSTIN A9 \ SELECTIVE PDGF TYROSINE;TYRPHOSTIN A9 99+%;Malonobene;2-(3,5-di-tert-butyl-4-hydroxybenzylidene)Malononitrile;Tyrphostin 9 (SF 6847);2,6-Di-tert-butyl-4-(2,2-dicyanovinyl)phenol;3,5-di-tert-Butyl-4-hydroxybenzylidenemalonitrile
• CAS NO: 10537-47-0
• Molecular Formula: C₁₈H₂₂N₂O
• Molecular Weight: 282.38
• Product Categories: Inhibitors
• Mol File: 10537-47-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 141-143℃ (ethanol )
• Boiling Point: 424.99°C (rough estimate)
• Flash Point: 187.7 ºC
• Appearance: yellow/solid
• Density: 1.0741 (rough estimate)
• Vapor Pressure: 1.55E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Store at RT
• Solubility: ethanol: 20 mg/mL
• PKA: 7.55±0.40(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• CAS DataBase Reference: TYRPHOSTIN A9(CAS DataBase Reference)
• NIST Chemistry Reference: TYRPHOSTIN A9(10537-47-0)
• EPA Substance Registry System: TYRPHOSTIN A9(10537-47-0)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: OO3737000
• HazardClass: 6.1
• Hazardous Substances Data: 10537-47-0(Hazardous Substances Data)

Usage

Description

Tyrphostin 9 (10537-47-0) inhibits PDGF receptor tyrosine kinase (IC50?= 1.2 μM)1and is a potent (10 nM) inhibitor of oxidative phosphorylation2. Inhibits cell growth by disrupting mitochondria.3 Tyrphostin 9 perturbs the golgi complex and blocks proliferation of vascular smooth muscle cells.4

Uses

Different sources of media describe the Uses of 10537-47-0 differently. You can refer to the following data:
1. Tyrphostin A9 can be used for inhibiting tyrosine kinase functions in C2C12 cells. It has also been used to disrupt membrane potential in mammalian cells.
2. SF 6847 is an inhibitor of EGFR with IC50 of 460 μM.
3. Selective inhibitor of PDGF receptor tyrosine kinase

General Description

A selective, cell-permeable, reversible, and substrate competitive inhibitor of the platelet-derived growth factor receptor tyrosine kinase (IC50 = 500 nM). Anti-proliferative agent. Uncoupler of oxidative phosphorylation. Induces apoptosis in vitro and cell growth arrest in NHL cell lines.

Biological Activity

Potent uncoupler of oxidative phosphorylation.

Biochem/physiol Actions

Cell permeable: yes

References

1) Bilder?et al. (1991),?Tyrphostins inhibit PDGF-induced DNA synthesis and associated early events in smooth muscle cells; Am. J. Physiol.,?260?C721 2) Terada?et al. (1981),?The interaction of highly active uncouplers with mitochondria; Biochim. Biophys. Acta,?639?225 3) Burger?et al. (1995),?Tyrphostin AG17, [3,5-Ditert-butyl-4-hydroxybenzylidene)-malononitrile], inhibits cell growth by disrupting mitochondria; Cancer Res.,?55?2794 4) Thyberg?et al. (1998),?Tyrphostin A9 and wortmannin perturb the Golgi complex and block proliferation of vascular smooth muscle cells; Eur. J. Cell Biol.,?76?33

InChI:InChI=1/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3

Synthetic route

malononitrile (109-77-3) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → malonoben (10537-47-0)

Conditions	Yield
With ammonium acetate In ethanol at 50 - 80℃;	95%
In N,N-dimethyl-formamide for 10h; Knoevenagel reaction; Heating;	83%
With piperidine In ethanol at 50 - 60℃; for 4h;	75.7%

phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone (6125-26-4) + malonoben (10537-47-0) → 2-(1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxo-2-phenylethyl)malononitrile

Conditions	Yield
With sodium dihydrogenphosphate; 1-hydroxy-1,2-benzodioxol-3-(1H)-one In dichloromethane at 20℃; for 8h; Inert atmosphere; Irradiation;	88%

malonoben (10537-47-0) + valinomycin (2001-95-8) → C54H90N6O18*C18H21N2O(1-)*K(1+) (83746-99-0)

Conditions	Yield
With potassium hydroxide In water at 20℃; for 0.166667h;

Upstream product

• 109-77-3 malononitrile 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 

Downstream Products

• 83746-99-0 C₅₄H₉₀N₆O₁₈*C₁₈H₂₁N₂O^(1-)*K⁽¹⁺⁾ 

Related news

TYRPHOSTIN A9 (cas 10537-47-0) improves blastocyst development in porcine embryos through induction of dynamin-related protein 1-dependent mitochondrial fission08/07/2019

Mitochondrial dynamics are associated with the development of porcine embryos. However, little is known about the effects of mitochondrial dynamics-related genes (Drp1 and pDrp1-Ser616) on early porcine embryo development. Here, we investigated the effect of Drp1-dependent mitochondrial fission ...detailed

Relevant articles and documents

METHODS AND COMPOSITIONS FOR TREATING OBESITY, PREVENTING WEIGHT GAIN, PROMOTING WEIGHT LOSS, PROMOTING SLIMMING, OR TREATING OR PREVENTING THE DEVELOPMENT OF DIABETES

The present invention relates to compositions and kits including a chemical uncoupler, such as tyrphostin 9 or precursor or a salt thereof, and compositions including a chemical uncoupler, such as tyrphostin 9 in combination with one or more therapeutic agents, for example, L-carnitine, which are useful, for example, in treating obesity, preventing weight gain, promoting weight loss/slimming, and/or treating or preventing the development of diabetes.

Tyrphostins I: Synthesis and Biological Activity of Protein Tyrosine Kinase Inhibitors

A novel class of low molecular weight proteine kinase inhibitors is described.These compounds consitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain.These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor.The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 102-103 higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases.These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors.The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth.These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases.We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.