386298-14-2Relevant academic research and scientific papers
Novel ligand SXH 1001 of transport protein TSPO, 18kDa as well as preparation method and application of novel ligand
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, (2017/07/21)
The invention relates to a novel ligand SXH 1001 of a transport protein TSPO, 18kDa as well as a preparation method and application of the novel ligand. The novel ligand is prepared by the following steps: synthesizing 4-methoxy benzoyl acetonitrile, namely dissolving 4-methoxy methyl benzoate in anhydrous acetonitrile, adding sodium methylate, performing a reflux reaction, performing vacuum evaporation to eliminate a solvent, adding water and ethyl acetate into residues, performing stirring fully, separating a water layer, adjusting the pH value to 8 with concentrated hydrochloric acid, performing extraction with ethyl acetate, and drying an organic layer with anhydrous sodium sulfate, and performing concentration and column chromatography to obtain a nearly white solid product 1 containing 4-methoxy benzoyl acetonitrile; synthesizing an intermediate product 2; synthesizing an intermediate product 3; synthesizing an intermediate product 4; synthesizing a final product 6. The application is that a molecular imaging probe for PET development is prepared by using 11C or 18F markers. The novel ligand has the advantages of high yield, high blood brain barrier pass rate, small noise and clear images.
TSPO ligands for cancer imaging and treatment
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Page/Page column 69; 70, (2016/10/24)
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.
Synthesis and structure-activity relationships of 5,6,7-substituted pyrazolopyrimidines: Discovery of a novel TSPO PET ligand for cancer imaging
Tang, Dewei,McKinley, Eliot T.,Hight, Matthew R.,Uddin, Md. Imam,Harp, Joel M.,Fu, Allie,Nickels, Michael L.,Buck, Jason R.,Manning, H. Charles
supporting information, p. 3429 - 3433 (2013/06/05)
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
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
Banister, Samuel D.,Wilkinson, Shane M.,Hanani, Raphy,Reynolds, Aaron J.,Hibbs, David E.,Kassiou, Michael
scheme or table, p. 3780 - 3783 (2012/09/10)
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.
Pyrazolo[1,5-a]pyrimidine acetamides: 4-Phenyl alkyl ether derivatives as potent ligands for the 18 kDa translocator protein (TSPO)
Reynolds, Aaron,Hanani, Raphy,Hibbs, David,Damont, Annelaure,Pozzo, Eleonora Da,Selleri, Silvia,Dollé, Frédéric,Martini, Claudia,Kassiou, Michael
supporting information; experimental part, p. 5799 - 5802 (2011/01/05)
Herein, we report the synthesis of four new phenyl alkyl ether derivatives (7, 9-11) of the pyrazolo[1,5-a]pyrimidine acetamide class, all of which showed high binding affinity and selectivity for the TSPO and, in the case of the propyl, propargyl, and bu
Microwave-assisted organic synthesis of a high-affinity pyrazolo-pyrimidinyl TSPO ligand
Tang, Dewei,Buck, Jason R.,Hight, Matthew R.,Manning, H. Charles
supporting information; experimental part, p. 4595 - 4598 (2010/09/18)
We herein report a dramatically improved total synthesis of the high-affinity translocator protein (TSPO) ligand DPA-714, featuring microwave-assisted organic synthesis (MAOS). Compared with previously described approaches, our novel MAOS method dramatica
2-ARYLPYRAZOLO[L,5-α]PYRIMIDIN-3-YL ACETAMIDE DERIVATIVES AS LIGANDS FOR TRANSLOCATOR PROTEIN (18 KDA)
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, (2008/06/13)
The invention provides compounds of formula (I) radiolabelled with 18F, 123I, 76Br, 124I or75Br and salts thereof, and a method of imaging translocator protein (18kDa) (TSPO) in a subject comprising a
Synthesis and in vivo evaluation of a novel peripheral benzodiazepine receptor PET radioligand
James, Michelle L.,Fulton, Roger R.,Henderson, David J.,Eberl, Stefan,Meikle, Steven R.,Thomson, Sally,Allan, Robin D.,Dolle, Frederic,Fulham, Michael J.,Kassiou, Michael
, p. 6188 - 6194 (2007/10/03)
The novel pyrazolopyrimidine ligand, N,N-diethyl-2-[2-(4-methoxyphenyl)-5, 7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-yl]-acetamide 1 (DPA-713), has been reported as a potent ligand for the peripheral benzodiazepine receptor (PBR) displaying an affinity of Ks
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands
Selleri,Bruni,Costagli,Costanzo,Guerrini,Ciciani,Costa,Martini
, p. 2661 - 2671 (2007/10/03)
A new class of N,N-diethyl-(2-arylpyrazolo[1,5-a]pyrimidin-3-yl)acetamides (3f-y), as azaisosters of Alpidem, was prepared following a novel synthetic method and their affinities for both the peripheral (PBR) and the central (CBR) benzodiazepine receptors were evaluated. Binding assays were carried out using both [3H]PK 11195 and [3H]Ro 5-4864 as radioligands for PBR, whereas [3H]Ro 15-1788 was used for CBR, in rat kidney and rat cortex, respectively. The tested compounds exhibited a broad range of binding affinities from as low as 0.76 nM to inactivity and most of them proved to be high selective ligands for PBR. The preliminary SAR studies suggested some of the structural features required for high affinity and selectivity; particularly the substituents on the pyrimidine moiety seemed to play an important role in PBR versus CBR selectivity. A subset of the highest affinity compounds was also tested for their ability to stimulate steroid biosynthesis in C6 glioma rat cells and some of these were found to increase pregnenolone formation with potency similar to Ro 5-4864 and PK 11195.
