DPA-713

DPA-713
Identifiers
	IUPAC name N,N-diethyl-2-(4-methoxyphenyl)-5,7-dimethylpyrazolopyrimidine-3-acetamide;
CAS Number	386297-97-8;
PubChem CID	11595759;
ChemSpider	9770519;
UNII	PQF723MLIV;
Chemical and physical data
Formula	C21H26N4O2
Molar mass	366.465 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-dimethylpyrazolopyrimidine-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]^[5] Radiation dosimetry and biodistribution of DPA-713 have been assessed in healthy volunteers, indicating that DPA-713 is a suitable radiotracer for imaging the TSPO in humans.^[6]^[7]

References

^ ^a ^b Selleri S, Bruni F, Costagli C, Costanzo A, Guerrini G, Ciciani G, Costa B, Martini C (2001). "2-Arylpyrazolopyrimidin-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.
^ ^a ^b Reynolds A, Hanani R, Hibbs D, Damont A, Da Pozzo E, Selleri S, Dollé F, Martini C, Kassiou M (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): 5799–802. doi:10.1016/j.bmcl.2010.07.135. PMID 20727749.
^ James ML, Fulton RR, Henderson DJ, Eberl S, Meikle SR, Thomson S, Allan RD, Dolle F, Fulham MJ, Kassiou M (November 2005). "Synthesis and in vivo evaluation of a novel peripheral benzodiazepine receptor PET radioligand". Bioorganic & Medicinal Chemistry. 13 (22): 6188–94. doi:10.1016/j.bmc.2005.06.030. PMID 16039131.
^ 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 (May 2006). "Improved synthesis of the peripheral benzodiazepine receptor ligand DPA-713 using methyl triflate". Applied Radiation and Isotopes. 64 (5): 570–3. doi:10.1016/j.apradiso.2005.12.003.
^ 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.
^ Endres CJ, Pomper MG, James M, Uzuner O, Hammoud DA, Watkins CC, Reynolds A, Hilton J, Dannals RF, Kassiou M (August 2009). "Initial evaluation of 11C-DPA-713, a novel TSPO PET ligand, in humans". Journal of Nuclear Medicine. 50 (8): 1276–82. doi:10.2967/jnumed.109.062265. PMC 2883612. PMID 19617321.
^ Endres CJ, Coughlin JM, Gage KL, Watkins CC, Kassiou M, Pomper MG (February 2012). "Radiation dosimetry and biodistribution of the TSPO ligand 11C-DPA-713 in humans". Journal of Nuclear Medicine. 53 (2): 330–5. doi:10.2967/jnumed.111.094565. PMC 3274766. PMID 22241913.

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[Selleri1-1] Selleri S, Bruni F, Costagli C, Costanzo A, Guerrini G, Ciciani G, Costa B, Martini C (2001). "2-Arylpyrazolopyrimidin-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.

[Reynolds_2010-2] Reynolds A, Hanani R, Hibbs D, Damont A, Da Pozzo E, Selleri S, Dollé F, Martini C, Kassiou M (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): 5799–802. doi:10.1016/j.bmcl.2010.07.135. PMID 20727749.

[3] James ML, Fulton RR, Henderson DJ, Eberl S, Meikle SR, Thomson S, Allan RD, Dolle F, Fulham MJ, Kassiou M (November 2005). "Synthesis and in vivo evaluation of a novel peripheral benzodiazepine receptor PET radioligand". Bioorganic & Medicinal Chemistry. 13 (22): 6188–94. doi:10.1016/j.bmc.2005.06.030. PMID 16039131.

[Thominiaux1-4] 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 (May 2006). "Improved synthesis of the peripheral benzodiazepine receptor ligand DPA-713 using methyl triflate". Applied Radiation and Isotopes. 64 (5): 570–3. doi:10.1016/j.apradiso.2005.12.003.

[Boutin1-5] 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.

[Endres1-6] Endres CJ, Pomper MG, James M, Uzuner O, Hammoud DA, Watkins CC, Reynolds A, Hilton J, Dannals RF, Kassiou M (August 2009). "Initial evaluation of 11C-DPA-713, a novel TSPO PET ligand, in humans". Journal of Nuclear Medicine. 50 (8): 1276–82. doi:10.2967/jnumed.109.062265. PMC 2883612. PMID 19617321.

[Endres2-7] Endres CJ, Coughlin JM, Gage KL, Watkins CC, Kassiou M, Pomper MG (February 2012). "Radiation dosimetry and biodistribution of the TSPO ligand 11C-DPA-713 in humans". Journal of Nuclear Medicine. 53 (2): 330–5. doi:10.2967/jnumed.111.094565. PMC 3274766. PMID 22241913.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

v t e Translocator protein modulators
Agonists	Alpidem DAA-1097 DAA-1106 DBI 17-50 fragment Deuterated etifoxine Dithranol (anthralin) Diazepam Diazepam binding inhibitor (DBI) DPA-713 DPA-714 Emapunil Etifoxine FGIN-1-27 FGIN-1-43 GML-1 Olesoxime Ro5-4864 SSR-180,575 W-18 YL-IPA08
Antagonists	PK-11195

Identifiers

IUPAC name N,N-diethyl-2-(4-methoxyphenyl)-5,7-dimethylpyrazolopyrimidine-3-acetamide
CAS Number	386297-97-8
PubChem CID	11595759
ChemSpider	9770519
UNII	PQF723MLIV
Chemical and physical data
Formula	C₂₁H₂₆N₄O₂
Molar mass	366.465 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

See also

References