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A carbon chain-extended glutamine boron trifluoride analog

A technology of amide derivatives and compounds, applied in the field of nuclear medicine diagnosis and treatment, can solve problems such as insufficient stability of glutamic acid probes, and achieve the effects of improving pharmacokinetic characteristics, improving stability, and improving lipophilicity

Active Publication Date: 2020-12-18
PEKING UNIV
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  • Summary
  • 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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  • A carbon chain-extended glutamine boron trifluoride analog
  • A carbon chain-extended glutamine boron trifluoride analog
  • A carbon chain-extended glutamine boron trifluoride analog

Examples

Experimental program
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Embodiment 1

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

[0055]

[0056]The specific synthesis steps are:

[0057]Step 1. Synthesis of compound 1:

[0058]Take monomethyl adipate (1eq) and tritylamine (1qe), O-benzotriazole-N,N,N',N'-tetramethylurea tetrafluoroborate (TBTU, 1eq) and dissolve React overnight in dichloromethane 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 is 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]Step 2. Synthesis of compound 2:

[0061]Dissolve compound 1 (1eq) in tetrahydrofuran, add lithium borohydride (2qe), and react at room temperature overnight. The reaction was quench...

experiment example 1

[0079]Experimental example 1 stability test

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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 medical treatment, and in particular to a glutamine boron trifluoride analog with extended carbon chain.Background technique[0002]Tumor is still a serious threat to human health. Effective diagnosis and character identification of tumors in a timely manner is very important in the process of tumor treatment. Positron Emission Tomography (PET) is a molecular imaging technique that relies 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, and then reconstruct it by computer to obtain a three-dimensional PET image of the human body.[0003]The basic feature of tumor cells is rapid growth and division, which requires a large amount of ...

Claims

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Application Information

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