1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide

Synonym(s):1,3-Benzoxazol-2-yl-3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide;7-(1,3-Benzoxazol-2-ylsulfanyl)-3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine;7-(2-Benzoxazolylthio)-3-(phenylmethyl)-3H-1,2,3-triazolo[4,5-d]pyrimidine;

CAS NO.：722456-31-7
Empirical Formula: C18H12N6OS
Molecular Weight: 360.39
MDL number: MFCD03407188
Update Date: 2024-11-19 23:02:33

1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide Structural

What is 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide?

Description

VAS-2870 (722456-31-7) is a NAD(P)H oxidase (Nox) inhibitor. Abolishes PDGF-mediated Nox activation and ROS production (100% at 10 μM). Inhibits PMA-induced oxidative burst in HL-60 cells (IC50=2 μM). VAS-2870 enhances TGF-β-induced apoptosis in liver tumor cells.

The Uses of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide

VAS 2870, is a NADPH oxidase (NOX) inhibitor.

The Uses of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide

VAS2870 has been used as a nicotinamide adenine dinucleotide phosphate (NADPH) oxidase (NOX) inhibitor:

to study the importance of NOX-derived reactive oxygen species in cytoskeletal organization, proper localization of E-cadherin and cell motility during zebrafish epiboly
to study the function of Nox2 and Nox4 in lipopolysaccharide (LPS)-induced intestinal injury in high-fat diet (HFD) fed mice
to reduce the reactive oxygen species level and study its influence on inhibiting the induction of trained innate immunity in monocytes

What are the applications of Application

VAS-2870 is a cell permeable specific NADPH oxidase inhibitor

General Description

A cell-permeable thiotriazolopyrimidine compound that acts as an effective NADPH oxidase (NOX) inhibitor (IC₅₀ = 10.6 μM against NOX activity in human neutrophil lysates) and is widely used for studying NOX-dependent cellular ROS formations in various cultures, including oxLDL-treated HUVEC (complete inhibition at 5 μM), PDGF-induced primary rat VSMC (vascular smooth muscle cells; complete inhibition at 10 μM), as well as aortic sections from spontaneously hypertensive rats (SHRs) (72% inhibition at 10 μM). Also shown to inhibit PDGF-BB-induced murine EB (embryonid body) vacularization (74% inhibition at 50 μM) and improve ACh-induced vasorelaxation of isolated rat aortic rings from both SHRs and non-hypertensive rats ex vivo (by 41.7 and 34.5%, respectively, at 10 μM).

Biochem/physiol Actions

VAS2870 is a cell-permeable and specific NADPH oxidase (NOX) inhibitor that effectively suppresses growth factor-mediated ROS liberation in VSMC.

storage

Store at +4°C

References

1) Freyhaus et al. (2006), Novel Nox inhibitor VAS2870 attenuates PDGF-dependent smooth muscle cell chemotaxis, but not proliferation; Cardiovasc. Res. 71 331 2) Stielow et al. (2006), Novel Nox inhibitor of oxLDL-induced reactive oxygen species formation in human endothelial cells; Biochem. Biophys. Res. Commun. 344 200 3) Sancho et al. (2011), The NADPH oxidase inhibitor VAS2870 impairs cell growth and enhances TGF-β-induced apoptosis of liver tumor cells; Biochem. Pharmacol. 81 917

Properties of 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide

Boiling point:	627.0±65.0 °C(Predicted)
Density	1.53±0.1 g/cm3(Predicted)
storage temp.	room temp
solubility	DMSO: ≥5mg/mL
form	Tan solid
pka	0.85±0.30(Predicted)
color	white to beige
Stability:	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Safety information for 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 1,3-benzoxazol-2-yl 3-benzyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl sulfide