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Dokumente

SML3379

Sigma-Aldrich

D159687

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C21H19ClN2O2
CAS-Nummer:
1155877-97-6
Molekulargewicht:
366.84
MDL-Nummer:
MFCD26793458
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear (Warmed)

Lagertemp.

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)

InChIKey

RJJLUTWHJUDZFP-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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