DPA-713

DPA-713
Identifiers
	IUPAC name N,N-diethyl-2-(4-methoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-acetamide;
CAS Number	386297-97-8;
PubChem CID	11595759;
ChemSpider	9770519;
CompTox Dashboard (EPA)	DTXSID001126663 ;
Chemical and physical data
Formula	C21H26N4O2
Molar mass	366.46 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)CC1=C2N=C(C=C(N2N=C1C3=CC=C(C=C3)OC)C)C;
	InChI InChI=1S/C21H26N4O2/c1-6-24(7-2)19(26)13-18-20(16-8-10-17(27-5)11-9-16)23-25-15(4)12-14(3)22-21(18)25/h8-12H,6-7,13H2,1-5H3; Key:ILZWUAWCTNWSFZ-UHFFFAOYSA-N;

DPA-713 or N,N-diethyl-2-(4-methoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-acetamide is a selective ligand for the translocator protein (TSPO).^[1]^[2]

The binding affinity of DPA-713 for TSPO is reported as K_i = 4.7 ± 0.2 nM.^[1]^[2]

DPA-713 has been radiolabelled with carbon-11 as a potential radiotracer for imaging the TSPO using positron emission tomography (PET).^[3]^[4] Radiation dosimetry and biodistribution of [¹¹C]DPA-713 have been assessed in healthy volunteers, indicating that [¹¹C]DPA-713 is a suitable radioatracer for imaging the TSPO in humans.^[5]^[6]

References

^ ^a ^b Selleri S, Bruni F, Costagli C, Costanzo A, Guerrini G, Ciciani G, Costa B, Martini C (2001). "2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands". Bioorg. Med. Chem. 9 (10): 2661–2671. doi:10.1016/S0968-0896(01)00192-4. {{cite journal}}: Cite has empty unknown parameter: |month= (help)
^ ^a ^b Reynolds A, Hanani R, Hibbs D, Damont A, Da Pozzo E, Selleri S, Dollé F, Martini C, Kassiou M (October 2010). "Pyrazolo[1,5-a]pyrimidine acetamides: 4-Phenyl alkyl ether derivatives as potent ligands for the 18 kDa translocator protein (TSPO)". Bioorg. Med. Chem. Lett. 20 (19): 5799–802. doi:10.1016/j.bmcl.2010.07.135. PMID 20727749.
^ Thominiaux C, Dollé F, James ML, Bramoullé Y, Boutin H, Besret L, Grégoire MC, Valette H, Bottlaender M, Tavitian B, Hantraye P, Selleri S, Kassiou M (2006). "Improved synthesis of the peripheral benzodiazepine receptor ligand [¹¹C]DPA-713 using [¹¹C]methyl triflate". Appl. Radiat. Isotopes. 64 (5): 570–573. doi:10.1016/j.apradiso.2005.12.003. {{cite journal}}: Cite has empty unknown parameter: |month= (help)
^ Boutin H, Chauveau F, Thominiaux C, Gregoire MC, James ML, Trebossen R, Hantraye P, Dolle F, Tavitian B, Kassiou M (2007). "¹¹C-DPA-713: A Novel Peripheral Benzodiazepine Receptor PET Ligand for In Vivo Imaging of Neuroinflammation". J. Nucl. Med. 48 (4): 573–581. doi:10.2967/jnumed.106.036764. {{cite journal}}: Cite has empty unknown parameter: |month= (help)
^ Endres CJ, Pomper MG, James M, Uzuner O, Hammoud DA, Watkins CC, Reynolds A, Hilton J, Dannals RF, Kassiou M (2009). "Initial Evaluation of ¹¹C-DPA-713, a Novel TSPO PET Ligand, in Humans". J. Nucl. Med. 50 (8): 1276–1282. doi:10.2967/jnumed.109.062265. {{cite journal}}: Cite has empty unknown parameter: |month= (help)
^ Endres CJ, Coughlin JM, Gage KL, Watkins CC, Kassiou M, Pomper MG (2012). "Radiation Dosimetry and Biodistribution of the TSPO Ligand ¹¹C-DPA-713 in Humans". J. Nucl. Med. 53 (2): 330–335. doi:10.2967/jnumed.111.094565. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

[Selleri1-1] Selleri S, Bruni F, Costagli C, Costanzo A, Guerrini G, Ciciani G, Costa B, Martini C (2001). "2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands". Bioorg. Med. Chem. 9 (10): 2661–2671. doi:10.1016/S0968-0896(01)00192-4. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

[Reynolds_2010-2] Reynolds A, Hanani R, Hibbs D, Damont A, Da Pozzo E, Selleri S, Dollé F, Martini C, Kassiou M (October 2010). "Pyrazolo[1,5-a]pyrimidine acetamides: 4-Phenyl alkyl ether derivatives as potent ligands for the 18 kDa translocator protein (TSPO)". Bioorg. Med. Chem. Lett. 20 (19): 5799–802. doi:10.1016/j.bmcl.2010.07.135. PMID 20727749.

[Thominiaux1-3] Thominiaux C, Dollé F, James ML, Bramoullé Y, Boutin H, Besret L, Grégoire MC, Valette H, Bottlaender M, Tavitian B, Hantraye P, Selleri S, Kassiou M (2006). "Improved synthesis of the peripheral benzodiazepine receptor ligand [¹¹C]DPA-713 using [¹¹C]methyl triflate". Appl. Radiat. Isotopes. 64 (5): 570–573. doi:10.1016/j.apradiso.2005.12.003. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

[Boutin1-4] Boutin H, Chauveau F, Thominiaux C, Gregoire MC, James ML, Trebossen R, Hantraye P, Dolle F, Tavitian B, Kassiou M (2007). "¹¹C-DPA-713: A Novel Peripheral Benzodiazepine Receptor PET Ligand for In Vivo Imaging of Neuroinflammation". J. Nucl. Med. 48 (4): 573–581. doi:10.2967/jnumed.106.036764. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

[Endres1-5] Endres CJ, Pomper MG, James M, Uzuner O, Hammoud DA, Watkins CC, Reynolds A, Hilton J, Dannals RF, Kassiou M (2009). "Initial Evaluation of ¹¹C-DPA-713, a Novel TSPO PET Ligand, in Humans". J. Nucl. Med. 50 (8): 1276–1282. doi:10.2967/jnumed.109.062265. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

[Endres2-6] Endres CJ, Coughlin JM, Gage KL, Watkins CC, Kassiou M, Pomper MG (2012). "Radiation Dosimetry and Biodistribution of the TSPO Ligand ¹¹C-DPA-713 in Humans". J. Nucl. Med. 53 (2): 330–335. doi:10.2967/jnumed.111.094565. {{cite journal}}: Cite has empty unknown parameter: |month= (help)

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See also

References