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PZ0380

Sigma-Aldrich

PF-04447943

≥98% (HPLC)

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Synonym(s):
1,5-Dihydro-6-[(3S,4S)-4-methyl-1-(2-pyrimidinylmethyl)-3-pyrrolidinyl]-1-(tetrahydro-2H-pyran-4-yl)-4H-pyrazolo[3,4-d]pyrimidin-4-one, 6-[(3S,4S)-4-Methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one, PF 4447943
Empirical Formula (Hill Notation):
C20H25N7O2
CAS Number:
1082744-20-4
Molecular Weight:
395.46
MDL number:
MFCD22665724
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

room temp

SMILES string

O=C1C2=C(N(C3CCOCC3)N=C2)N=C([C@H]4[C@H](C)CN(CC5=NC=CC=N5)C4)N1

InChI

1S/C20H25N7O2/c1-13-10-26(12-17-21-5-2-6-22-17)11-16(13)18-24-19-15(20(28)25-18)9-23-27(19)14-3-7-29-8-4-14/h2,5-6,9,13-14,16H,3-4,7-8,10-12H2,1H3,(H,24,25,28)/t13-,16-/m1/s1

InChI key

IWXUVYOOUMLUTQ-CZUORRHYSA-N

Related Categories

Biochem/physiol Actions

PF-04447943 is a potent selective brain penetrant phosphodiesterase PDE9A inhibitor both potency (8 nM) and selectivity (>10 μM versus all the PDEs except PDE1C at >1 μM). It has been investigated for the treatment of cognitive disorders including Alzheimer′s Disease. PF-04447943 increased neurite outgrowth and synapse formation in hippocampal neurons in culture, exhibited synaptic stabilization in an amyloid precursor protein (APP) transgenic mouse model, and improved memory and enhanced attention in several animal models.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Patrick R Verhoest et al.
Journal of medicinal chemistry, 55(21), 9045-9054 (2012-07-12)
6-[(3S,4S)-4-Methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943) is a novel PDE9A inhibitor identified using parallel synthetic chemistry and structure-based drug design (SBDD) and has advanced into clinical trials. Selectivity for PDE9A over other PDE family members was achieved by targeting key residue differences between the
Ryan T Cameron et al.
FEBS open bio, 7(1), 64-73 (2017-01-18)
Phosphodiesterase (PDE) inhibitors are currently under evaluation as agents that may facilitate the improvement of cognitive impairment associated with Alzheimer's disease. Our aim was to determine whether inhibitors of PDEs 4, 5 and 9 could alleviate the cytotoxic effects of
Dávid Nagy et al.
Experimental neurology, 263, 122-131 (2014-10-16)
Several neurophysiological abnormalities have been described in Huntington's disease, including auditory gating deficit, which are considered to reflect impaired brain information-processing. Since transgenic animal models of Huntington's disease capture basic neuropathology of the disorder, auditory gating was studied in BACHD

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