Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

SML2121

Sigma-Aldrich

A-33

≥98% (HPLC)

Synonym(s):

2-(4-{[2-(5-Chlorothiophen-2-yl)-5-ethyl-6-methylpyrimidin-4-yl]amino}phenyl)acetic acid, 2-[4-[[2-(5-Chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]acetic acid, 4-[[2-(5-Chloro-2-thienyl)-5-ethyl-6-methyl-4-pyrimidinyl]amino]-benzeneacetic acid, A33

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C19H18ClN3O2S
CAS Number:
915082-52-9
Molecular Weight:
387.88
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(O)CC1=CC=C(NC2=NC(C3=CC=C(Cl)S3)=NC(C)=C2CC)C=C1

Biochem/physiol Actions

A-33 (A33) is a potent and selective catalytic site-targeting PDE4B inhibitor (IC50 = 15 nM/PDE4B vs. 1.7 μM/PDE4D) that effectively prevents PDE4B-medicated cellular cAMP hydrolysis (150%/320% increased cAMP level with 100 nM/1 μM A-33 pre-treament in murine hippocampal HT-22 cells following 10 nM isoproterenol stimulation) in vitro and inhibits LPS-induced TNF-α production in mice in vivo (ID50 = 14 mg/kg p.o.). When administered via intraperitoneal injection, A-33 improves cognitive function in a rat model of traumatic brain injury (0.3 mg/kg i.p.) and exhibits antidepressant property in mice (0.3-1 mg/kg i.p.) in vivo.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Timothy J Hagen et al.
Bioorganic & medicinal chemistry letters, 24(16), 4031-4034 (2014-07-08)
In this study we report a series of triazine derivatives that are potent inhibitors of PDE4B. We also provide a series of structure activity relationships that demonstrate the triazine core can be used to generate subtype selective inhibitors of PDE4B
David J Titus et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 36(27), 7095-7108 (2016-07-08)
Learning and memory impairments are common in traumatic brain injury (TBI) survivors. However, there are no effective treatments to improve TBI-induced learning and memory impairments. TBI results in decreased cAMP signaling and reduced cAMP-response-element binding protein (CREB) activation, a critical
David Fox et al.
Cellular signalling, 26(3), 657-663 (2013-12-24)
Phosphodiesterase-4B (PDE4B) regulates the pro-inflammatory Toll Receptor -Tumor Necrosis Factor α (TNFα) pathway in monocytes, macrophages and microglial cells. As such, it is an important, although under-exploited molecular target for anti-inflammatory drugs. This is due in part to the difficulty
Kenji Naganuma et al.
Bioorganic & medicinal chemistry letters, 19(12), 3174-3176 (2009-05-19)
In this study the first PDE4B selective inhibitor is described. Optimization of lead 2-arylpyrimidine derivatives afforded a series of potent PDE4B inhibitors with >100-fold selectivity over the PDE4D isozyme. With a good pharmacokinetic profile, a selected compound exhibited potent anti-inflammatory
Chong Zhang et al.
Scientific reports, 7, 40115-40115 (2017-01-06)
Inhibition of cyclic AMP (cAMP)-specific phosphodiesterase 4 (PDE4) has been proposed as a potential treatment for a series of neuropsychological conditions such as depression, anxiety and memory loss. However, the specific involvement of each of the PDE4 subtypes (PDE4A, 4B

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service