133406-29-8

Basic information

• Product Name: ST034307
• Synonyms: ST034307;6-chloro-2-(trichloromethyl)-4H-chromen-4-one
• CAS NO: 133406-29-8
• Molecular Formula: C10H4Cl4O2
• Molecular Weight: 297.94956
• Mol File: 133406-29-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 329.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.674±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 6 mg/ml)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: ST034307(CAS DataBase Reference)
• NIST Chemistry Reference: ST034307(133406-29-8)
• EPA Substance Registry System: ST034307(133406-29-8)

Safety Data

• Hazardous Substances Data: 133406-29-8(Hazardous Substances Data)

Usage

Description

ST-034307 (133406-29-8) is a?novel selective adenylyl cyclase 1 (AC1) inhibitor, IC50=2.3 μM . Inhibits calcium2+-stimulated cAMP accumulation in HEK cells stably transfected with AC11. It was also shown to inhibit AC1 stimulated by forskolin- and Gαs-coupled receptors in HEK-AC1 cells. ?It enhanced μ-opioid receptor-mediated inhibition of AC1 but it blocked heterologous sensitization of AC1 caused by chronic μ-opioid receptor activation.1,3?Displays analgesic properties in a mouse model of inflammatory pain.1?A useful tool for exploring the involvement of AC1 in cellular signalling.2

Uses

ST 034307 is a useful intermediate.

References

1) Brust?et al.?(2017),?Identification of a selective small-molecule inhibitor of type 1 adenylyl cyclase activity with analgesic properties; Sci. Signal,?10?eaah5381 2) Jiang?et al,?(2018),?Cyclic-Nucleotide- and HCN-Channel-Mediated Phototransduction in Intrinsically Photosensitive Retinal Ganglion Cells;. Cell?175?652 3) Watts (2018),?Selective Adenylyl Cyclase Type 1 Inhibitors as Potential Opioid Alternatives For Chronic Pain;?Neuropsychopharmacology?43?215

Upstream product

• 69693-00-1 6-chloro-2-methyl-4H-chromen-4-one 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 288087-81-0 (Z)-3-Amino-4,4,4-trichloro-1-(5-chloro-2-hydroxy-phenyl)-but-2-en-1-one 

Downstream Products

• 19484-57-2 6-chloro-4-hydroxycoumarin 

Relevant articles and documents

Condensation of 2-hydroxyacetophenones with trichloroacetonitrile as a route to 2-trichloromethylchromones and 4-hydroxycoumarins

Condensation of 2-hydroxyacetophenones with trichloroacetonitrile in the presence of N-methylanilinomagnesium bromide affords hydroxyaryl β-amino-β-trichloromethylvinyl ketones, which are converted into 2-trichloromethylchromones upon treatment with concentrated HCl. The resulting compounds react with alcoholic solutions of NH3 or KOH to form 3-amino-1-(2-hydroxyaryl)-4,4,4-trichlorobut-2-en-1-ones and 4-hydroxycoumarins, respectively.