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Divinyl sulfamide linker as well as preparation and application thereof

A technology of bisethylene sulfonamide and ethylene sulfonamide, which is applied in the field of sulfur-sulfur bonds, can solve the problems of unsatisfactory stability of maleimide compounds and complicated preparation of monosulfone compounds

Active Publication Date: 2017-11-28
SHANGHAI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of monosulfone compounds is cumbersome, while the stability of maleimide compounds is not ideal

Method used

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  • Divinyl sulfamide linker as well as preparation and application thereof
  • Divinyl sulfamide linker as well as preparation and application thereof
  • Divinyl sulfamide linker as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of bisethylenesulfonamide linker 1

[0053]

[0054] Using the general procedure A, add 675.8 mg of p-acetylaniline as the raw material, and add the others in equivalent amount, and react at 0°C for 10 minutes. Add 3ml CH in general step A 2 Cl 2 and 3g 60-100 mesh silica gel, mix well and spin dry. Ethyl acetate / petroleum ether = 1 / 6 was used as the eluent, and 770 mg of the product was obtained by passing through the column.

[0055] 1 H NMR (500MHz, CDCl 3 )δ8.01(d, J=8.5Hz, 2H), 7.38(d, J=8.5Hz, 2H), 7.07(dd, J=16.5, 9.9Hz, 2H), 6.30(d, J=16.6Hz, 2H), 6.18(d, J=9.8Hz, 2H), 2.62(s, 3H)ppm. 13 CNMR (126MHz, CDCl 3 )δ196.95, 138.48, 137.71, 136.07, 131.33, 130.30, 129.62, 26.94ppm. ESI-HRMS calcd for C 12 h 14 NO 5 S 2 [(M+H) + ]: 316.0313, found: 316.0296

Embodiment 2

[0057] Preparation of bisethylenesulfonamide linker 2

[0058]

[0059] Using the general procedure A, add 552.5 mg of p-nitroaniline as the raw material, and add the others in equivalent amounts, and react at 0°C for 1 hour. Add 3ml CH in general step A 2 Cl 2 and 2.5g 60-100 mesh silica gel, mix well and spin dry. Using ethyl acetate / petroleum ether=1 / 6 as eluent, the product was passed through the column to obtain 100 mg.

[0060] 1 H NMR (500MHz, CDCl 3 )δ8.33-8.24 (m, 2H), 7.49-7.42 (m, 2H), 7.07 (dd, J=16.5, 9.8Hz, 2H), 6.31 (dd, J=16.5, 0.9Hz, 2H), 6.22 (dd, J=9.9, 0.9Hz, 2H)ppm. 13 C NMR (126MHz, CDCl 3 )δ148.85, 139.24, 135.86, 132.19, 130.80, 124.90ppm. EI-GCMS calcd forC 10 h 11 N 2 o 6 S 2 (M): 317.9980, found: 218.20

Embodiment 3

[0062] Preparation of bisethylenesulfonamide linker 3

[0063]

[0064] Using the general procedure A, add 1.23 g of p-methoxyaniline as the raw material, and add the others in equivalent amount, and react at 0°C for 10 minutes. Add 10ml CH in general step A 2 Cl 2 and 5g 60-100 mesh silica gel, mix well and spin dry. Using ethyl acetate / petroleum ether = 1 / 6 as eluent, the product was passed through the column to obtain 1.93 g of the product.

[0065] 1 H NMR (500MHz, CDCl 3 )δ7.22-7.14(m, 2H), 7.04(dd, J=16.6, 9.9Hz, 2H), 6.94-6.88(m, 2H), 6.28(d, J=16.6Hz, 2H), 6.13(d , J=9.8Hz, 2H), 3.82(s, 3H)ppm. 13 C NMR (126MHz, CDCl 3 )δ161.17, 136.21, 132.19, 129.70, 125.97, 114.91, 55.67ppm.ESI-HRMScalcd for C 11 h 14 NO 5 S 2 [(M+H) + ]: 304.0313, found: 304.0298

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Abstract

The invention provides a divinyl sulfamide linker as well as preparation and an application thereof. The divinyl sulfamide linker has the structural formula shown in the formula I or the formula II. One end of the novel divinyl sulfamide linker can be coupled with a polypeptide or protein, and the other end can be connected with an affinity tag or a tracing fluorescent substance or an active drug.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals and biotechnology, and specifically relates to a novel linker (linker) and its preparation, and its application to specific coupling of affinity markers, tracer fluorescent substances and active drugs to polypeptides, Methods on accessible sulfur-sulfur bonds in proteins. The linker and the coupling method involved in the present invention can be used to prepare target tracer diagnostic reagents, tumor target therapy drugs, etc., and can control the drug / target ratio (DAR). Background technique [0002] Selective chemical modification of proteins is of great importance in the fields of biochemical and biomedical research. The use of chemical means to develop protein modification methods has been successfully applied in many fields, such as: protein fluorescent labeling, intracellular biological process detection, protein conjugates for treatment, diagnosis, etc. The most popular and important a...

Claims

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Application Information

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IPC IPC(8): C07C311/11C07C303/38C07D213/76C07D295/26C07D495/04C07D405/12C07D491/22C07K1/107
CPCC07C311/11C07D213/76C07D295/26C07D405/12C07D491/22C07D495/04C07K1/1077
Inventor 姜标陈红莉李至宏
Owner SHANGHAI TECH UNIV
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