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DPA-714

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Chemical compound Pharmaceutical compound
DPA-714
Identifiers
IUPAC name
  • N,N-diethyl-2--5,7-dimethylpyrazolopyrimidine-3-acetamide
CAS Number
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H27FN4O2
Molar mass398.482 g·mol
3D model (JSmol)
SMILES
  • CCN(CC)C(=O)Cc1c(nn2c1nc(cc2C)C)c3ccc(cc3)OCCF
InChI
  • InChI=1S/C22H27FN4O2/c1-5-26(6-2)20(28)14-19-21(17-7-9-18(10-8-17)29-12-11-23)25-27-16(4)13-15(3)24-22(19)27/h7-10,13H,5-6,11-12,14H2,1-4H3
  • Key:FLZZFWBNYJNHMY-UHFFFAOYSA-N

DPA-714 or N,N-diethyl-2--5,7-dimethylpyrazolopyrimidine-3-acetamide is a selective ligand for the translocator protein (TSPO) currently under evaluation for several clinical applications. For this reason, a practical, multigram synthetic route for its preparation has been described.

The binding affinity of DPA-714 for TSPO is reported as Ki = 7.0 ± 0.4 nM.

DPA-714 is currently under investigation as a potential radiopharmaceutical for imaging TSPO in living systems using positron emission tomography (PET). DPA-714, along with other members of the DPA class of TSPO ligands, has been shown to decrease microglial activation and increase neuronal survival in a quinolinic acid rat model of excitotoxic neurodegeneration, suggesting potential neuroprotective effects.

See also

References

  1. Reynolds A, Hanani R, Hibbs D, Damont A, Da Pozzo E, Selleri S, et al. (October 2010). "Pyrazolopyrimidine acetamides: 4-Phenyl alkyl ether derivatives as potent ligands for the 18 kDa translocator protein (TSPO)". Bioorganic & Medicinal Chemistry Letters. 20 (19): 5799–5802. doi:10.1016/j.bmcl.2010.07.135. PMID 20727749.
  2. Banister SD, Wilkinson SM, Hanani R, Reynolds AJ, Hibbs DE, Kassiou M (2012). "A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolopyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands". Tetrahedron Letters. 53 (29): 3780–3783. doi:10.1016/j.tetlet.2012.05.044.
  3. James ML, Fulton RR, Vercoullie J, Henderson DJ, Garreau L, Chalon S, et al. (May 2008). "DPA-714, a new translocator protein-specific ligand: synthesis, radiofluorination, and pharmacologic characterization". Journal of Nuclear Medicine. 49 (5): 814–822. doi:10.2967/jnumed.107.046151. PMID 18413395.
  4. Damont A, Hinnen F, Kuhnast B, Schöllhorn-Peyronneau MA, James M, Luus C, Tavitian B, Kassiou M, Dollé F (2008). "Radiosynthesis of DPA-714, a selective radioligand for imaging the translocator protein (18 kDa) with PET". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (7): 286–292. doi:10.1002/jlcr.1523.
  5. Leaver KR, Reynolds A, Bodard S, Guilloteau D, Chalon S, Kassiou M (February 2012). "Effects of translocator protein (18 kDa) ligands on microglial activation and neuronal death in the quinolinic-acid-injected rat striatum". ACS Chemical Neuroscience. 3 (2): 114–119. doi:10.1021/cn200099e. PMC 3369788. PMID 22860181.
Translocator protein modulators
Agonists
Antagonists
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