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SML3379

Sigma-Aldrich

D159687

≥98% (HPLC)

Synonyme(s) :

1-(4-((3′-Chloro-6-methoxy-[1,1′-biphenyl]-3-yl)methyl)phenyl)urea, D 159687, N-[4-[(3′-Chloro-6-methoxy[1,1′-biphenyl]-3-yl)methyl]phenyl]urea, [4-(3′-Chloro-6-methoxy-biphenyl-3-ylmethyl)phenyl]urea, [4-[[3-(3-Chlorophenyl)-4-methoxyphenyl]methyl]phenyl]urea

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About This Item

Formule empirique (notation de Hill):
C21H19ClN2O2
Numéro CAS:
1155877-97-6
Poids moléculaire :
366.84
Numéro MDL:
MFCD26793458
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear (Warmed)

Température de stockage

2-8°C

InChI

1S/C21H19ClN2O2/c1-26-20-10-7-15(12-19(20)16-3-2-4-17(22)13-16)11-14-5-8-18(9-6-14)24-21(23)25/h2-10,12-13H,11H2,1H3,(H3,23,24,25)

Clé InChI

RJJLUTWHJUDZFP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

D159687 is a brain-penetrant, orally available, highly potent and selective negative allosteric modulator (NAM) against phosphodiesterase 4 (PDE4) subtype PDE4D (hPDE4D7 IC50 = 27 nM; PDE4A1/B1/C1 IC50 = 2.50/1.47/6.80 μM; IC50 ≥29 μM against PDE1/2/3/5/7/8/9/10/11 subtypes). Comparing to Rolipram, D159678 offers similar in vivo efficacy on long-term memory formation by novel object recognition test (MED = 3 μg/kg mouse iv., 1 μg/kg rat p.o.), while being more effective in the scopolamine-impaired Y-maze tests (D159678/Rolipram MED = 0.1/1 μg/kg mouse iv. or 30/100 μg/kg mouse p.o.) and much less emetic in shrews/dog/monkeys (by 100-/3000-/500-fold).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Alex B Burgin et al.
Nature biotechnology, 28(1), 63-70 (2009-12-29)
Phosphodiesterase 4 (PDE4), the primary cAMP-hydrolyzing enzyme in cells, is a promising drug target for a wide range of conditions. Here we present seven co-crystal structures of PDE4 and bound inhibitors that show the regulatory domain closed across the active
David J Titus et al.
Neurobiology of learning and memory, 148, 38-49 (2018-01-03)
Traumatic brain injury (TBI) significantly decreases cyclic AMP (cAMP) signaling which produces long-term synaptic plasticity deficits and chronic learning and memory impairments. Phosphodiesterase 4 (PDE4) is a major family of cAMP hydrolyzing enzymes in the brain and of the four
Jane S Sutcliffe et al.
PloS one, 9(7), e102449-e102449 (2014-07-23)
Cyclic adenosine monophosphate (cAMP) signalling plays an important role in synaptic plasticity and information processing in the hippocampal and basal ganglia systems. The augmentation of cAMP signalling through the selective inhibition of phosphodiesterases represents a viable strategy to treat disorders
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

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