A 205804 Property

Melting point:

198-199℃

Boiling point:

581.3±45.0 °C(Predicted)

Density 

1.40±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

≥30 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

pka

15.12±0.30(Predicted)

form 

powder to crystal

color 

White to Orange to Green

Safety

HS Code 

2934.99.9001

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

A 205804 Chemical Properties,Usage,Production

Description

A-205804 is a potent inhibitor of E-selectin and ICAM-1 expression in human vascular endothelial cells stimulated with TNF-α (IC₅₀s = 20 and 25 nM, respectively). It does not block expression of VCAM-1 (IC₅₀ > 1,000 nM).

Uses

4-[(4-Methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide is a reagent used in the preparation of selective inhibitors of cell adhesion molecule expression in human endothelial cells.

Definition

ChEBI: 4-[(4-methylphenyl)thio]-2-thieno[2,3-c]pyridinecarboxamide is an aryl sulfide.

Biological Activity

Selective inhibitor of E-selectin and ICAM-1 expression (IC 50 values are 20, 25 and > 1000 nM for TNF- α -induced E-selectin, ICAM-1 and VCAM-1 expression respectively). Effective inhibitor of cell-cell adhesion in an in vitro flow experiment.

storage

Store at +4°C

References

[1]. stewart, a.o., et al., discovery of inhibitors of cell adhesion molecule expression in human endothelial cells. 1. selective inhibition of icam-1 and e-selectin expression. j med chem, 2001. 44(6): p. 988-1002.
[2]. chang, c.z., et al., valproic acid attenuates intercellular adhesion molecule-1 and e-selectin through a chemokine ligand 5 dependent mechanism and subarachnoid hemorrhage induced vasospasm in a rat model. j inflamm (lond), 2015. 12: p. 27.
[3]. zhu, g.d., et al., selective inhibition of icam-1 and e-selectin expression in human endothelial cells. 2. aryl modifications of 4-(aryloxy)thieno[2,3-c]pyridines with fine-tuning at c-2 carbamides. j med chem, 2001. 44(21): p. 3469-87.
[4]. zhu, g.d., et al., synthesis and mode of action of (125)i- and (3)h-labeled thieno[2,3-c]pyridine antagonists of cell adhesion molecule expression. j org chem, 2002. 67(3): p. 943-8.