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Glutamine boron trifluoride analogue with elongated carbon chain

A technology of amide derivatives and compounds, which is applied in the field of nuclear medicine diagnosis and treatment, can solve the problems of insufficient stability of glutamic acid probes, and achieve the effects of improving pharmacokinetic characteristics, prolonging the half-life of drug activity, and excellent stability

Active Publication Date: 2019-05-21
PEKING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the problem of insufficient stability of glutamic acid probes in the prior art, a new reagent for tumor PET imaging diagnosis and / or BNCT precision medicine is provided, specifically providing a carbon chain-extended glutamine boron trifluoride analogs

Method used

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  • Glutamine boron trifluoride analogue with elongated carbon chain
  • Glutamine boron trifluoride analogue with elongated carbon chain
  • Glutamine boron trifluoride analogue with elongated carbon chain

Examples

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Embodiment 1

[0054] This embodiment provides a carbon chain-extended glutamine boron trifluoride molecular probe, and the reaction process for its preparation is as follows:

[0055]

[0056] Concrete synthetic steps are:

[0057] The 1st step, the synthesis of compound 1:

[0058] Dissolve monomethyl adipate (1eq) with tritylamine (1qe), O-benzotriazole-N,N,N',N'-tetramethyluronium tetrafluoroboric acid (TBTU, 1eq) In dichloromethane, react overnight at room temperature. The reaction was quenched by adding water, extracted with ethyl acetate, dried and the solvent was removed under reduced pressure. Column chromatography separated to obtain the corresponding tribenzamide compound, namely compound 1.

[0059] NMR results of compound 1: 1H NMR (400MHz, CDCl3, ppm): δ7.35–7.08(m,15H),6.58(s,1H),3.65(s,3H),2.45–2.23(m,4H), 1.75–1.44 (m, 4H).

[0060] The 2nd step, the synthesis of compound 2:

[0061] Dissolve compound 1 (1eq) in tetrahydrofuran, add lithium borohydride (2qe), and re...

experiment example 1

[0079] Experimental Example 1 Stability Detection

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Abstract

The invention relates to a glutamine boron trifluoride analogue with an elongated carbon chain. The glutamine boron trifluoride analogue has a structure as shown in formula I, wherein Ca is S configuration or R configuration; F is 18F or 19F, and n is integer from 4 to 10. The invention further provides a corresponding preparation method and an application thereof. The compound can be used for preparing a PET imaging agent; the compound has the advantages of being high in stability, low in background shooting, high in contrast ratio, and high in tumor-muscle ratio when being used for PET imaging; the compound can be used for preparing boron neutron capture therapy medicine due to small toxicity and high enrichment efficiency, and the compound has comparatively high integrated application prospect in PET diagnosis and BNCT therapy.

Description

technical field [0001] The invention belongs to the field of nuclear medicine diagnosis and treatment, and specifically relates to a reagent for tumor PET imaging diagnosis and / or BNCT precision medicine, in particular to a boron trifluoride glutamine analogue with carbon chain extension. Background technique [0002] Tumor is still a serious threat to human health. Timely and effective diagnosis and identification of tumors are very important in the treatment of tumors. Positron Emission Tomography (PET) is a molecular imaging technique based on radioactive molecular probes. The basis of PET technology is the detection of paired photons emitted by positron annihilation, which can accurately locate and quantify the distribution of radioactivity in the body. After computer reconstruction, a three-dimensional PET image of the human body can be obtained. [0003] The basic feature of tumor cells is rapid growth and division, which requires the intake of a large amount of basic...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07B59/00A61K31/69A61K51/04A61K41/00A61P35/00A61K101/02
Inventor 刘志博陈俊艺
Owner PEKING UNIV
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