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B8279

Sigma-Aldrich

4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one

solid

Synonym(s):

Ro 20-1724

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About This Item

Empirical Formula (Hill Notation):
C15H22N2O3
CAS Number:
29925-17-5
Molecular Weight:
278.35
MDL number:
MFCD00077397
UNSPSC Code:
41106305
PubChem Substance ID:
24278195
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (HPLC)

form

solid

solubility

ethanol: 7 mg/mL
H2O: insoluble

storage temp.

room temp

SMILES string

CCCCOc1cc(CC2CNC(=O)N2)ccc1OC

InChI

1S/C15H22N2O3/c1-3-4-7-20-14-9-11(5-6-13(14)19-2)8-12-10-16-15(18)17-12/h5-6,9,12H,3-4,7-8,10H2,1-2H3,(H2,16,17,18)

InChI key

PDMUULPVBYQBBK-UHFFFAOYSA-N

Gene Information

human ... LITAF(9516) , PDE4B(5142) , PRKAR1A(5573) , PRKAR1AP(5574) , PRKAR1B(5575) , PRKAR2A(5576) , PRKAR2B(5577)
rat ... Pde4a(25638)

Application

4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one has been used:
  • as a cyclic adenosine monophosphate (cAMP) phosphodiesterase inhibitor to treat cells for the determination of intracellular cAMP levels
  • as a component of serum-free medium
  • as phosphodiesterase inhibitor in order to study the effects of protease-activated receptor-1 (PAR-1) activation on cAMP levels

Biochem/physiol Actions

Inhibitor of cAMP phosphodiesterase. IC50 33 μM in vascular smooth muscle of the aorta.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B Huang et al.
Circulation research, 85(9), 848-855 (1999-10-26)
Three weeks after myocardial infarction (MI) in the rat, remodeled hypertrophy of noninfarcted myocardium is at its maximum and the heart is in a compensated stage with no evidence of heart failure. Our hemodynamic measurements at this stage showed a
Farhan A Khawaja et al.
Hippocampus, 17(12), 1143-1148 (2007-09-21)
The entorhinal cortex (EC), located in the medial temporal lobe (MTL) of the brain, plays an important functional role in the MTL memory circuit. Medial EC (MEC) Layer II stellate cells (SCs) serve as one of the most prominent target
Chien-Chung Chen et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 35(7), 1605-1617 (2010-03-20)
The mossy fiber synapses onto hippocampal CA3 neurons show unique molecular features and a wide dynamic range of plasticity. Although acute stress has been well recognized to alter bidirectional long-term synaptic plasticity in the hippocampal CA1 region and dentate gyrus
Regulation of sleep by the short neuropeptide F (sNPF) in Drosophila melanogaster
Chen W, et al.
Insect Biochemistry and Molecular Biology, 43(9), 809-819 (2013)
Protease-activated receptor-1 stimulates Ca2+-dependent Cl- secretion in human intestinal epithelial cells
Buresi MC, et al.
American Journal of Physiology: Gastrointestinal and Liver Physiology, 281(2), G323-G332 (2001)
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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