ChemicalBook Product Catalog Biochemical Engineering Inhibitors Epigenetics Sirtuin Inhibitors 2-Cyano-3-[5-(2,5-dichlorophenyl)-2-furanyl]-N-5-quinolinyl-2-propenamide

2-Cyano-3-[5-(2,5-dichlorophenyl)-2-furanyl]-N-5-quinolinyl-2-propenamide

Product Name2-Cyano-3-[5-(2,5-dichlorophenyl)-2-furanyl]-N-5-quinolinyl-2-propenamide
CAS304896-28-4
MFC23H13Cl2N3O2
MW434.27
EINECS
MOL File304896-28-4.mol

Chemical Properties

Boiling point	675.1±55.0 °C(Predicted)
Density	1.445±0.06 g/cm3(Predicted)
storage temp.	room temp
solubility	DMSO: soluble2mg/mL, clear (warmed)
form	Yellow solid
pka	8.87±0.43(Predicted)
color	White to Yellow to Orange
InChI	1S/C23H13Cl2N3O2/c24-15-6-8-19(25)18(12-15)22-9-7-16(30-22)11-14(13-26)23(29)28-21-5-1-4-20-17(21)3-2-10-27-20/h1-12H,(H,28,29)/b14-11+
InChIKey	SVENPFFEMUOOGK-SDNWHVSQSA-N
SMILES	Clc1ccc(Cl)c(c1)-c2ccc(\C=C(/C#N)C(=O)Nc3cccc4ncccc34)o2

Safety Information

Hazard Codes	Xi
Risk Statements	36
Safety Statements	26
WGK Germany	3
HS Code	2934.99.4400
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

AGK2 is a SIRT2 inhibitor. AGK2 has been used in a study to determine that SIRT2 inhibition induces cell death and decreases the intracellular ATP level. AGK2 also rescues dopamine neurons from α-synuclein toxicity in Parkinson′s disease models.

Definition

ChEBI: 2-cyano-3-[5-(2,5-dichlorophenyl)-2-furanyl]-N-(5-quinolinyl)-2-propenamide is a member of quinolines.

Biological Activity

Selective inhibitor of SIRT2 (IC 50 = 3.5 μ M). Displays no activity at SIRT1 and SIRT3 at concentrations up to 40 μ M. Reduces α -synuclein-mediated toxicity in in vitro and in vivo models of Parkinson's disease.

Biochem/physiol Actions

AGK2 is a SIRT2 inhibitor. AGK2 rescues dopamine neurons from α-synuclein toxicity in Parkinson′s disease models. IC50 for SIRT2 = 3.5 uM. AGK2 is >15-fold more selective for SIRT2 than SIRT1 and SIRT3. AGK2 may be the most selective SIRT2 inhibitor available.

in vivo

AGK2 significantly reduces mortality and decreases levels of cytokines in blood (TNF-α: 298.3±24.6 vs 26.8±2.8 pg/mL, p=0.0034; IL-6: 633.4±82.8 vs 232.6±133.0 pg/mL, p=0.0344) and peritoneal fluid (IL-6: 704.8±67.7 vs 391.4±98.5 pg/mL, p=0.033) compare to vehicle control. AGK2 also suppresses the TNF-α and IL-6 production in the culturing splenocytes (TNF-α: 68.1±6.4 vs 23.9±2.8 pg/mL, p=0.0009; IL-6: 73.1±4.2 vs 49.6±3.0 pg/mL; p=0.0051)^[4].

IC 50

SIRT2: 3.5 μM (IC₅₀); SIRT1: 30 μM (IC₅₀); SIRT3: 91 μM (IC₅₀)

References

[1]. outeiro tf, kontopoulos e, altmann sm, et al. sirtuin 2 inhibitors rescue alpha-synuclein-mediated toxicity in models of parkinson's disease. science, 2007, 317(5837): 516-519.
[2]. scuderi c, stecca c, bronzuoli mr, et al. sirtuin modulators control reactive gliosis in an in vitro model of alzheimer's disease. front pharmacol, 2014, 5: 89.
[3]. rotili d, tarantino d, nebbioso a, et al. discovery of salermide-related sirtuin inhibitors: binding mode studies and antiproliferative effects in cancer cells including cancer stem cells. j med chem, 2012, 55(24): 10937-10947.

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