868072-17-7

Basic information

• Product Name: 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide
• Synonyms: 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide
• CAS NO: 868072-17-7
• Molecular Weight: 352.436
• Mol File: 868072-17-7.mol

Chemical Properties

• CAS DataBase Reference: 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide(868072-17-7)
• EPA Substance Registry System: 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide(868072-17-7)

Safety Data

• Hazardous Substances Data: 868072-17-7(Hazardous Substances Data)

Upstream product

• 884504-22-7 3-(4-isopropoxyphenyl)-3-oxopropanenitrile 
• 1384517-65-0 2-[3-amino-5-(4-isopropoxyphenyl)-1H-pyrazol-4-yl]-N,N-diethylacetamide 
• 1384517-66-1 2-[2-(4-isopropoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 
• 35826-59-6 methyl 4-isopropoxybenzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 2315-36-8 2-Chloro-N,N-diethylacetamide 
• 1384517-64-9 3-cyano-N,N-diethyl-4-(4-isopropoxyphenyl)-4-oxobutanamide 
• 123-54-6 acetylacetone 
• 122488-52-2 ethyl 4-isopropoxybenzoate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 386298-19-7 2-[3-amino-5-(4'-methoxyphenyl)-1H-pyrazol-4-yl]-N,N-diethylacetamide 
• 386298-14-2 N,N-diethyl-[3-cyano-4-(4-methoxyphenyl)-4-oxo]butanamide 
• 3672-47-7 3-oxo-3-(4'-methoxyphenyl)propanenitrile 
• 121-98-2 methyl 4-methoxybenzoate 

Downstream Products

• 958233-17-5 2-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenoxy)ethyl 4-methylbenzenesulfonate 
• 1353642-17-7 3-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenoxy)propyl but-2-ynoate 
• 1353642-15-5 C₂₇H₃₄N₄O₄ 
• 1353642-16-6 C₂₆⁽¹³⁾CH₃₄N₄O₄ 
• 1009080-27-6 N,N-diethyl-2-(2-(4-(3-hydroxypropoxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide 
• 1254174-27-0 2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 
• 1454618-50-8 tert-butyl 2-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[l,5-a]pyrimidin-2-yl)phenoxy)ethylcarbamate 

Relevant articles and documents

Efficient tritiation of the translocator protein (18kDa) selective ligand DPA-714

DPA-714 (N,N-diethyl-2-(2-(4-(2-fluoroethoxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide) is a recently discovered fluorinated ligand of the translocator protein 18 kDa (TSPO). Labelled with the short-lived positron emitter fluorine-18, th

Targeting Mitochondria in Tumor-Associated Macrophages using a Dendrimer-Conjugated TSPO Ligand that Stimulates Antitumor Signaling in Glioblastoma

Mitochondria mediate critical cellular processes, including proliferation, apoptosis, and immune responses; as such, their dysfunction is pathogenic in many neurodegenerative disorders and cancers. In glioblastoma, targeted delivery of mitochondria-focuse

Radioactive molecular probe taking TSPO as target point as well as preparation method and application thereof

The invention discloses a small molecular organic compound with a specific targeting TSPO (Transfer Protein). The structure of the small molecular organic compound comprises a benzene ring, pyrazolo imidazole and a diethyl acetamide structure. The P-tolue

[18F] DPA-714 (N, N-diethyl-2-(2-(4-(2-[18]F-fluoroethyoxy)phenyl)-5, 7-dimethylpyrazolo[1, 5-a]pyrimidin-3-yl)aceamide) derivative and preparation and application methods thereof

The invention discloses a [18F] DPA-174 derivative. The [18F] DPA-174 derivative is prepared by modifying the benzene ring structure of or prolonging the carbon chain structure of a [18]F DPA-174 imaging agent. The invention also discloses preparation and application methods of the [18F] DPA-174 derivative. The [18F] DPA-174 derivative is simple in preparation, easy to implement, high in labellingyield and good in repeatability and can help in real time observe and in vivo monitor the status of intracerebral neuroinflammation of an animal model as well as the changes of the major organs and tissues of the animal model; the prepared imaging agents can achieve imaging effects on neuroinflammation; the [18F] DPAF imaging agent can achieve a high signal-to-noise ratio on neuroinflammation lesions to provide possibility for further monitoring and assessing the diagnosis and treatment effects on neuroinflammation..

Synthesis and evaluation of novel potent TSPO PET ligands with 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamide

Translocator protein (TSPO) expression is closely related with neuroinflammation and neuronal damage which might cause several central nervous system diseases. Herein, a series of TSPO ligands (11a–c and 13a–d) with a 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamide structure were prepared and evaluated via an in vitro binding assay. Most of the novel ligands exhibited a nano-molar affinity for TSPO, which was better than that of DPA-714. Particularly, 11a exhibited a subnano-molar TSPO binding affinity with suitable lipophilicity for in vivo brain studies. After radiolabeling with fluorine-18, [18F]11a was used for a dynamic positron emission tomography (PET) study in a rat LPS-induced neuroinflammation model; the inflammatory lesion was clearly visualized with a superior target-to-background ratio compared to [18F]DPA-714. An immunohistochemical examination of the dissected brains confirmed that the uptake location of [18F]11a in the PET study was consistent with a positively activated microglia region. This study proved that [18F]11a could be employed as a potential PET tracer for detecting neuroinflammation and could give possibility for diagnosis of other diseases, such as cancers related with TSPO expression.

TSPO ligands for cancer imaging and treatment

Embodiments of the present invention relates to compounds of the following formula: as well as compositions, methods of imaging and methods of treating subjects comprising the use of the compound, wherein the variables are defined herein.

Ether analogues of DPA-714 with subnanomolar affinity for the translocator protein (TSPO)

Sixteen new phenyl alkyl ether derivatives (12, 14-28) of the 5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylacetamide (DPA) class were synthesized and evaluated in a competition binding assay against [3H]PK11195 using 18 kDa translocator protein (TSPO) derived from rat kidney mitochondrial fractions. All analogues showed superior binding affinities for TSPO compared to DPA-713 (5) and DPA-714 (6). Picomolar affinities were observed for this class of TSPO ligands in this assay for the first time, with phenethyl ether 28 showing the greatest affinity (Ki Combining double low line 0.13 nM). Additionally, all analogues increased pregnenolone biosynthesis (134-331% above baseline) in a rat C6 glioma cell steroidogenesis assay.

Synthesis and structure-activity relationships of 5,6,7-substituted pyrazolopyrimidines: Discovery of a novel TSPO PET ligand for cancer imaging

Focused library synthesis and structure-activity relationship development of 5,6,7-substituted pyrazolopyrimidines led to the discovery of 2-(5,7-diethyl-2-(4-(2-fluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-N, N-diethylacetamide (6b), a novel transl

Synthesis and characterization of an MRI Gd-based probe designed to target the translocator protein

DPA-713 is the lead compound of a recently reported pyrazolo[1,5-a] pyrimidineacetamide series, targeting the translocator protein (TSPO 18 kDa), and as such, this structure, as well as closely related derivatives, have been already successfully used as p

A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7- dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands

A practical, multigram approach to the 2-(2-(4-alkoxyphenyl)-5,7- dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of ligands targeting the translocator protein (TSPO) is described. This synthetic route offers several improvements over all previously described sequences, including the isolation of intermediates without resort to chromatography. The common precursor to the DPA class of high affinity TSPO ligands, N,N-diethyl-2-(2-(4- hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide, was produced in 40% yield over six steps, and was cleanly alkylated to give multigram quantities of several DPA analogues in 90-96% yield after recrystallization.