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Sulfonyl fluoride compound and application thereof

A sulfonyl fluoride-based compound technology, applied in the field of sulfonyl fluoride-based compounds, can solve the problems of unfavorable clinical transformation and harsh labeling conditions, and achieve the effects of high yield, high affinity and simple labeling conditions

Active Publication Date: 2021-10-26
首都医科大学脑重大疾病研究中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

18 F-labeled radioactive molecular probes usually require an activated ester nucleophilic heating reaction with a high energy barrier, and the labeling conditions are usually harsh, which is not conducive to clinical transformation

Method used

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  • Sulfonyl fluoride compound and application thereof
  • Sulfonyl fluoride compound and application thereof
  • Sulfonyl fluoride compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0033] Example 1 (S)-2-amino-3-(4-((fluorosulfonyl)oxy)phenyl)propionic acid

[0034] The structural formula is as follows:

[0035]

[0036] The synthetic route is as follows:

[0037]

[0038] (1) Synthesis of (S)-2-(((tert-butoxycarbonyl)amino)tert-butyl-3-(4-((fluorosulfonyl)oxy)phenyl)propionate

[0039] Compound (S)-2-amino-3-(4-((fluorosulfonyl)oxy)phenyl)propionic acid (0.5g, 1.48mmol) was dissolved in 20mL of dichloromethane, in ice water, and then Add triethylamine (0.59mL, 5.93mmol), SO 2 A balloon of ClF gas was inserted under the liquid and reacted overnight. Afterwards, the reaction solution was added to water, dried over anhydrous sodium sulfate, concentrated, and column chromatographed to obtain the product (0.36 g, 58.4%). 1H NMR (300MHz, CDCl3) δ7.30(s, 4H), 5.09(d, J=4.9Hz, 1H), 4.47(d, J=5.5Hz, 1H), 3.09(s, 2H), 1.42(d ,J=7.2Hz,18H).13C NMR(75MHz,CDCl3)δ170.46,155.03,148.97,137.66,131.43,120.67,82.52,79.72,77.44,77.02,76.59,54.67,38.13,28.25,28Sc...

example 2

[0042] Example 2 (2S, 4S)-2,5-diamino-4-(4-((fluorosulfonyl)oxy)benzyl)-5-oxopentanoic acid

[0043] The structural formula is as follows:

[0044]

[0045] The synthetic route is as follows:

[0046]

[0047] (1) Synthesis of tert-butyl (2S, 4S)-2-(((tert-butoxycarbonyl)amino)-4-(4-((fluorosulfonyl)oxy)benzyl)-5-oxo-5 -((2,4,5-Trimethoxybenzyl)amino)pentanoate

[0048]The compound (2S, 4S)-2-(((tert-butoxycarbonyl)amino)-4-(4-hydroxybenzyl)-5-oxo-5-((2,4,5-trimethoxybenzyl Base) amino) tert-butyl valerate (0.2g, 0.34mmol) was dissolved in 20mL of dichloromethane, as in ice water, then added triethylamine (0.13mL, 1.3mmol), SO 2 A balloon of ClF gas was inserted under the liquid and reacted overnight. Afterwards, the reaction solution was added to water, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to obtain the product (0.13 g, 56.2%). 1 H NMR (300MHz, CDCl3) δ7.09(d, J=6.1Hz, 2H), 6.92(d, J=6.6Hz, 2H), 5.94(s, 2H), 5.19...

example 3

[0051] Example 3 2-amino-3-(4-((fluorosulfonyl)oxy)phenyl)-2-methylpropionic acid

[0052] The structural formula is as follows:

[0053]

[0054] The synthetic route is as follows:

[0055]

[0056] (1) Synthesis of tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-((fluorosulfonyl)oxy)phenyl)-2-methylpropionate

[0057] The compound 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)-2-methylpropanoic acid tert-butyl ester (0.2 g, 0.56 mmol) was dissolved in 20 mL of dichloromethane, as After adding triethylamine (2.2mL, 2.27mmol) to ice water, the SO 2 A balloon of ClF gas was inserted under the liquid and reacted overnight. Afterwards, the reaction solution was added to water, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to obtain the product (0.15 g, 63.4%). HRMS calcd for; C19H28FNO7S 433.1571found, 434.1689[M+H] + .

[0058] (2) Synthesis of 2-amino-3-(4-((fluorosulfonyl)oxy)phenyl)-2-methylpropionic acid

[0059] Th...

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Abstract

The invention discloses a sulfonyl fluoride compound. Compared with reported PET imaging agents for targeted amino acid transporter, fibroblast activating protein, vesicular monoamine transporter 2, serotonin receptor and prostate specific membrane antigen protein change related diseases, the series of sulfonyl fluoride compounds designed and synthesized by the invention have the advantages of simple labeling conditions, high yield and high affinity. The invention belongs to the technical field of radiopharmaceutical chemistry and nuclear medicine.

Description

technical field [0001] The invention belongs to the technical field of radiopharmaceutical chemistry and nuclear medicine, and specifically relates to a sulfonyl fluoride compound and its application. Background technique [0002] Positron tomography (PET) can non-invasively, quantitatively and dynamically provide molecular and physiological information of different cancerous sites in vitro, and has high sensitivity, strong specificity, good safety, and whole-body imaging. It is a powerful tool for clinical diagnosis of cardiovascular and cerebrovascular diseases. Two important conditions to realize PET imaging: PET instrument and molecular probe. The research of specific imaging probe is the current emphasis and difficulty. Finding effective targets related to diseases, designing molecules that specifically bind to them, developing ideal radioactive molecular imaging probes, and developing new PET imaging drugs are important ways to solve early diagnosis of related diseas...

Claims

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Application Information

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IPC IPC(8): C07C305/26C07D401/12C07D455/06C07K5/062A61K51/04A61K51/08A61K101/02
CPCC07C305/26C07D401/12C07D455/06C07K5/06026A61K51/04A61K51/0455A61K51/0459A61K51/08C07B2200/07
Inventor 吴泽辉吉训明孙雨丽陈华龙程雪波蒋增郑伟杨庭钰于子越
Owner 首都医科大学脑重大疾病研究中心
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