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Novel <18>F-marked pyrazolo[1,5-a]pyrimidine compound and preparation and application thereof

A 5-a, pyrazolo technology, applied in organic chemistry, radioactive carriers, etc., to achieve the effect of simple synthesis, short total labeling time, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2011-07-06
BEIJING NORMAL UNIVERSITY
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Problems solved by technology

Although 18 F-labeled pyrazolo[1,5-a]pyrimidines have not been reported as PET tumor imaging agents, but CDK 2 Overexpressed in tumor cells, as a CDK 2 Inhibitors of pyrazolo[1,5-a]pyrimidines 18 After F labeling, it has the potential to become a specific and targeted PET tumor imaging agent

Method used

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  • Novel &lt;18&gt;F-marked pyrazolo[1,5-a]pyrimidine compound and preparation and application thereof
  • Novel &lt;18&gt;F-marked pyrazolo[1,5-a]pyrimidine compound and preparation and application thereof
  • Novel &lt;18&gt;F-marked pyrazolo[1,5-a]pyrimidine compound and preparation and application thereof

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Embodiment

[0079] Prepared according to the following steps is R in formula A 1 = H, R 2 = 2-fluoro 18-4-nitro, n=1 compounds, including labeling precursors (R in formula B 1 = H, R 2 =2-fluoro18-4-nitro, n=1 compound) synthesis and precursor compound 18 F marks two parts.

[0080] 1) labeled precursor (R in formula B 1 = H, R 2 =2-fluoro 18-4-nitro, n=1 compound) synthesis

[0081] 1.1 Synthesis of ethoxymethylene malononitrile, see formula F:

[0082]

[0083] Formula F

[0084] 9.9 g (150 mmol) of malononitrile, 33.3 g (225 mmol) of triethyl orthoformate and 38.4 g (376.5 mmol) of acetic anhydride were added to a 250 ml one-necked flask. After reflux reaction for 6 hours, cool, add activated carbon, heat to reflux for 30 minutes, heat filter, wash the filter cake with hot ethanol, put the filtrate in the refrigerator overnight, and suction filter to obtain light yellow flaky crystals with a yield of 84%.

[0085] The synthesis of 1.23-amino-4-cyanopyrazole, see formula G:

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Abstract

The invention discloses a novel <18>F-marked pyrazolo[1,5-a]pyrimidine compound. The compound is characterized by having a parent structure 3-cyan pyrazolo[1,5-a]pyrimidine, wherein the fifth bit of the compound has substituents R, namely methyl, chloromethyl, (N,N-dimethylamino)methyl, acetoxymethyl, hydroxymethyl and carboxyl; amido on the seventh bit of the compound is connected with fluorine-18 through a carbon chain with n carbon atoms; and the structure of the compound is shown as a formula A. The compound is simple to synthesize and mark with operation easiness. The compound can maintain higher concentration for a longer time in a tumor tissue, and has low absorption rate or high clearing rate in normal tissues and blood. In particular, the compound has very high ratios of tumor to blood ratio and tumor to muscle tissues. The invention also relates to application of the compound serving as a PET (Polyethylene Terephthalate) brain tumor developer. In a formula A of the compound, R=CH3, CH2Cl, CH2N(CH3)2, CH2OCOCH3 and CH2OH; and COOHn=2,3.

Description

Technical field: [0001] The invention relates to a new type of toluenesulfonyloxy group as a leaving group 18 F-labeled pyrazolo[1,5-a]pyrimidine compound, its chemical preparation method and its application as a tumor (especially brain tumor) imaging agent for positron emission tomography (PET). Background technique: [0002] The early diagnosis of tumors is a hot spot in today's medicine, and positron emission tomography (PET) has received great attention as an increasingly popular means, so the breakthrough of early diagnosis of tumors depends on PET tumor imaging agents development. [0003] radionuclide 18 F is very suitable as an imaging nuclide for PET because of its excellent nuclide properties. [0004] Tumor occurrence is directly related to the cell cycle. Cyclin E and cyclin-dependent protein kinase 2 (CyclinE-CDK 2 ) complex in cell cycle G 1 It is directly related to the transition point of / S phase, which is the downstream target gene of various oncogene...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K51/04A61K101/02
Inventor 齐传民刘航许荆立贺勇李桂霞丁瑞王潇冯曼
Owner BEIJING NORMAL UNIVERSITY
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