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Method for modifying amino in molecule by using imidazoline quaternary ammonium salt and application thereof

A technology of quaternary ammonium salt and amino group, applied in the field of biochemistry, can solve problems such as coupling reaction of oxazoline quaternary ammonium salt and amino acid residue not involved

Active Publication Date: 2020-10-20
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of these studies involved the coupling reaction of the oxazoline quaternary ammonium salt with amino acid residues.

Method used

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  • Method for modifying amino in molecule by using imidazoline quaternary ammonium salt and application thereof
  • Method for modifying amino in molecule by using imidazoline quaternary ammonium salt and application thereof
  • Method for modifying amino in molecule by using imidazoline quaternary ammonium salt and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of embodiment 1 compound 2-1

[0060]

[0061] With substituted or unsubstituted 2-chloroquinolone or 2-chloroisoquinoline compounds as raw materials, refer to literature (Li Bo (LiBo) et al., Discovery of N-substituted 3-arylisoquinolone derivatives asantitumor agents originating from O-substituted 3 2-(2,2-Dimethoxyethoxy base) quinoline, 2-(2,2-dimethoxyethylthio)quinoline or 2-(2,2-dimethoxyethylselenyl)quinoline (0.13mmol), then dissolved in dry Keep it dry in ether hydrochloride (5ml), react overnight, and spin dry the excess ether hydrochloride to obtain intermediate 1. a) directly dissolve the obtained intermediate 1 in n-butanol or water (10ml), and add the amine nucleophile 2-amino-N-methylacetamide hydrochloride (0.26mmol); or b) the obtained Intermediate 1 was added to the amine nucleophile 2-amino-N-methylacetamide hydrochloride (0.26 mmol) in n-butanol or aqueous solution. Then add or not add triethylamine or potassium phosphate (0.26...

Embodiment 2

[0062] The preparation of embodiment 2 compound 2-2

[0063]

[0064] Except that the nucleophile was replaced with (S)-2-amino-N-methylpropionamide hydrochloride, the preparation method was the same as in Example 1 to obtain compound 2-2 with a yield of 92%. 1 H NMR (600MHz, CDCl 3 )δ7.80(d, J=8.8Hz, 1H), 7.67(d, J=8.3Hz, 1H), 7.59(d, J=7.9Hz, 1H), 7.53(t, J=7.3Hz, 1H) ,7.27–7.21(m,1H),7.10(s,1H),6.61(d,J=8.8Hz,1H),5.28(d,J=5.9Hz,1H),4.72(p,J=6.7Hz, 1H), 2.78(d, J=4.9Hz, 3H), 1.52(d, J=7.0Hz, 3H). 13 C NMR (150MHz, CDCl 3 ) δ 174.3, 155.8, 147.4, 137.6, 129.7, 127.5, 126.1, 123.6, 122.6, 112.0, 50.7, 26.1, 18.1. HRMS (ESI): C 13 h 16 N 3 O[M+H] + Calculated value: 230.1288, measured value: 230.1288.

Embodiment 3

[0065] The preparation of embodiment 3 compound 2-3

[0066]

[0067] Except that the nucleophile was replaced with 2-amino-N,3,3-trimethylbutanamide hydrochloride, the preparation method was the same as that of Example 1 to obtain compound 2-3 with a yield of 66%. 1 H NMR (400MHz, CDCl 3 )δ7.82(d, J=8.9Hz, 1H), 7.69(d, J=8.4Hz, 1H), 7.61(s, 1H), 7.57–7.52(m, 1H), 7.25(t, J=8.0 Hz,1H),6.70(d,J=8.9Hz,1H),6.44(s,1H),5.68(s,1H),4.50(d,J=7.8Hz,1H),2.80(d,J=4.9 Hz,3H),1.14(s,9H). 13 CNMR (125MHz, CDCl 3 ) δ 172.6, 156.3, 147.1, 137.8, 129.7, 127.5, 125.7, 123.6, 122.5, 112.0, 34.4, 27.0, 26.1. HRMS (ESI): C 16 h 22 N 3 O[M+H] + Calculated: 272.1757, Found: 272.1756.

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Abstract

The present invention relates to a method for modifying or labeling amino in a molecule. An imidazoline quaternary ammonium salt represented by a following formula 1 is used to modify or label amino in a molecule, and the molecule includes an amino acid ester, an amino amide, or a peptide / protein. The method has the advantages of economy and site selectivity, and has a huge potential application value in the fields of drug molecule synthesis, probe molecule and diagnostic marker reagent development, and the like.

Description

technical field [0001] This application belongs to the field of biochemistry, and in particular relates to a method and application of using oxazoline quaternary ammonium salt (or zolinium, zolinium) to modify or label amino groups in molecules. Background technique [0002] Quaternary ammonium salts (quaternary ammonium salts) are compounds in which all four hydrogen atoms in ammonium ions are replaced by hydrocarbon groups. The four hydrocarbon groups can be the same or different; the anions are mostly halogen anions (F, Cl, Br, I), or acid radicals (such as HSO 4 - 、RCOO - wait). Quaternary ammonium salt compounds are widely used in medicine, chemical industry and other fields, such as fungicides, disinfectants, soft antistatic agents, flocculant demulsifiers, drilling fluids, VES fracturing fluids, drag reducers, enhancers, etc. Thickener, anionic synergist, phase transfer catalyst, etc. [0003] Among quaternary ammonium salts, azole quaternary ammonium salts are v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38C07D401/12C07D217/22C07K1/113C07K1/13
CPCC07D215/38C07D401/12C07D217/22C07K1/113C07K1/13C07B2200/07C07K1/1077C07K5/06052C07K5/0812C07K7/06C07K5/06139
Inventor 李波刘鹏孙海国奚萌宇徐志建张勇朱维良
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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