[F18]-2-(2-(4-(2-Fluoroethoxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide

ID: ALA451770

Chembl Id: CHEMBL451770

Cas Number: 958233-09-5

PubChem CID: 23582365

Max Phase: Phase

Molecular Formula: C22H27FN4O2

Molecular Weight: 398.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: [18f]dpa-714 | [18f]dpa-714|DPA-714 F-18|CHEMBL451770|SCHEMBL12373846|0VMV8Z3972|18F-DPA-714|BAY858102|BAY85-8102|958233-09-5|N,N-DIETHYL-(2-(4-(2-(18F)FLUOROETHOXY)PHENYL)-5,7-DIMETHYLPYRAZOLO(1,5-A)PYRIMIDINE-3-YL)ACETAMIDE|J3.034.965B|Q27895632|PYRAZOLO(1,5-A)PYRIMIDINE-3-ACETAMIDE, N,N-DIETHYL-2-(4-(2-(FLUORO-18F)ETHOXY)PHENYL)-5,7-DIMETHYL-

Canonical SMILES:  CCN(CC)C(=O)Cc1c(-c2ccc(OCC[18F])cc2)nn2c(C)cc(C)nc12

Standard 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/i23-1

Standard InChI Key:  FLZZFWBNYJNHMY-VNRZBHCFSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 398.48

Molecular Weight (Monoisotopic): 398.2118

AlogP: 3.77

#Rotatable Bonds: 8

Polar Surface Area: 59.73

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.43

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.77

References

1. Fookes CJ, Pham TQ, Mattner F, Greguric I, Loc'h C, Liu X, Berghofer P, Shepherd R, Gregoire MC, Katsifis A..  (2008)  Synthesis and biological evaluation of substituted [18F]imidazo[1,2-a]pyridines and [18F]pyrazolo[1,5-a]pyrimidines for the study of the peripheral benzodiazepine receptor using positron emission tomography.,  51  (13): [PMID:18557607] [10.1021/jm7014556]

2. Tang D, McKinley ET, Hight MR, Uddin MI, Harp JM, Fu A, Nickels ML, Buck JR, Manning HC..  (2013)  Synthesis and structure-activity relationships of 5,6,7-substituted pyrazolopyrimidines: discovery of a novel TSPO PET ligand for cancer imaging.,  56  (8): [PMID:23521048] [10.1021/jm4001874]

3. Médran-Navarrete V, Damont A, Peyronneau MA, Kuhnast B, Bernards N, Pottier G, Marguet F, Puech F, Boisgard R, Dollé F..  (2014)  Preparation and evaluation of novel pyrazolo[1,5-a]pyrimidine acetamides, closely related to DPA-714, as potent ligands for imaging the TSPO 18kDa with PET.,  24  (6): [PMID:24560538] [10.1016/j.bmcl.2014.01.080]

4. Peyronneau MA, Saba W, Goutal S, Damont A, Dollé F, Kassiou M, Bottlaender M, Valette H..  (2013)  Metabolism and quantification of [(18)F]DPA-714, a new TSPO positron emission tomography radioligand.,  41  (1): [PMID:23065531] [10.1124/dmd.112.046342]

5. Unpublished dataset, 

6. Barresi E, Robello M, Costa B, Da Pozzo E, Baglini E, Salerno S, Da Settimo F, Martini C, Taliani S..  (2021)  An update into the medicinal chemistry of translocator protein (TSPO) ligands.,  209  [PMID:33081988] [10.1016/j.ejmech.2020.112924]

Source

Source(2):

• Scientific Literature
• Clinical Candidates