BP-1-102

BP-1-102 Property

Boiling point:

749.2±70.0 °C(Predicted)

Density 

1.474±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO:15.0(Max Conc. mg/mL);23.9(Max Conc. mM)

form 

A crystalline solid

pka

3.15±0.10(Predicted)

color 

White to off-white

InChIKey

WNVSFFVDMUSXSX-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(N(CC2=CC=C(C3CCCCC3)C=C2)C(CN(C)S(C2=C(F)C(F)=C(F)C(F)=C2F)(=O)=O)=O)C=C1O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

BP-1-102 Chemical Properties,Usage,Production

Uses

BP-1-102 is a potent and selective STAT3 inhibitor. STAT3 is a cytoplasmic transcription factor that induces the expression of genes related to tumorigenesis. BP 1-102 exhibits antitumor activity against Waldenstrom macroglobulinemia, a rare form of B cell non-Hodgkin lymphoma.

Biological Activity

Primary Target
Stat3

Synthesis

General method: Benzyl-protected salicylic acid (1 eq.) was dissolved in a stirred solvent mixture of methanol/tetrahydrofuran (1:1, v/v, 0.1 M). After thorough degassing, 10% palladium/carbon catalyst (10 mg/mmol) was cautiously added. The solution was bubbled with hydrogen gas for 5 minutes, followed by continuous stirring of the reaction under hydrogen atmosphere for 3 hours. Upon completion of the reaction, the hydrogen was removed, the palladium catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure.

in vivo

IC 50

STAT3: 6.8 μM (IC₅₀)

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5605 - 5609
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1102 - 1107
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 18, p. 7190 - 7200