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Benzene sulfonamide hydroxyl derivative and intermediate thereof as well as preparation method and application thereof

A benzenesulfonamide, imine-based technology, applied in the field of new compounds and their preparation, can solve the problem of blanks in molecular imaging research, and achieve good carbonic anhydrase inhibitory activity, less non-specific absorption, and strong hydrophilicity. Effect

Active Publication Date: 2009-11-25
SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] As a marker of tumor hypoxia, CAIX has a close relationship with the therapeutic effect of tumors, so it is a promising target for molecular imaging diagnosis of tumors. The current molecular biology and medical research on CA IX A lot of important progress has been made, but the molecular imaging research targeting CA IX is still almost blank at home and abroad

Method used

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  • Benzene sulfonamide hydroxyl derivative and intermediate thereof as well as preparation method and application thereof
  • Benzene sulfonamide hydroxyl derivative and intermediate thereof as well as preparation method and application thereof
  • Benzene sulfonamide hydroxyl derivative and intermediate thereof as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0055] Example 1 Synthesis of 4-[(4-chloro-6(2--hydroxyethoxy)-1,3,5-triazine-2-imino]benzenesulfonamide (compound 4)

[0056] Dissolve compound 3 (1.6g, 5mmol), NaOH (0.2g, 5mmol) in 8ml of ethylene glycol, stir at a constant temperature of 45°C, follow the reaction with TCL, developer: V (ethyl acetate): V (petroleum ether) = 2: 1, until the reaction of compound 3 is complete, add 10ml of water, cool, the solid precipitates out, filter the solid to obtain a white solid powder, dry in a vacuum oven, separate through a silica gel column (the eluent is pure ethyl acetate, collect Rf= 0.30 component), the solvent was removed by rotary evaporation, and vacuum-dried to obtain 0.95 g of white solid powder with a yield of 55.2%.

[0057] Result identification

[0058] 1 HNMR (DMSO-d6) δ: 10.92 (m, 1H, NH), 7.810-7.757 (d, 4H, aromatic), 7.252 (s, 2H, NH 2 ), 4.940-4-913 (m, 1H, OH), 4.364-4.453 (t, 2H, CH 2 ), 3.709-3.62 (q, 2H, CH 2 ).

[0059] MS m / z (%): 344.0 (M + -H, 100...

Embodiment 2

[0061] Example 2 Synthesis of 4-[(4-chloro-6(2--hydroxyethoxy)-1,3,5-triazine-2-imino]benzenesulfonamide (compound 4)

[0062] Dissolve compound 3 (1.6g, 5mmol), KOH (0.34g, 6mmol) in 13ml of ethylene glycol, stir at a constant temperature of 30°C, follow the reaction with TCL, developer: V (ethyl acetate): V (petroleum ether) = 2: 1, until the reaction of compound 3 is complete, add 10ml of water, cool, the solid precipitates out, filter the solid to obtain a white solid powder, dry in a vacuum oven, separate through a silica gel column (the eluent is pure ethyl acetate, collect Rf= 0.30 component), the solvent was removed by rotary evaporation, and vacuum-dried to obtain 0.62 g of white solid powder with a yield of 36.0%.

Embodiment 3

[0063] Example 3 Synthesis of 4-[(4-chloro-6(2--hydroxyethoxy)-1,3,5-triazine-2-imino]benzenesulfonamide (compound 4)

[0064] Dissolve compound 3 (1.6g, 5mmol), NaOH (0.22g, 5.5mmol) in 11ml of ethylene glycol, stir at a constant temperature of 50°C, follow the reaction with TCL, developing solvent: V (ethyl acetate): V (petroleum ether )=2:1, until compound 3 has reacted, add 10ml of water, cooling, solid precipitation, filter solid, obtain white solid powder, dry in a vacuum oven, separate through silica gel column (eluent is pure ethyl acetate, collect Rf =0.30 component), the solvent was removed by rotary evaporation, and vacuum-dried to obtain 0.85 g of white solid powder with a yield of 49.4%.

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Abstract

The invention discloses a benzene sulfonic amide hydroxyl derivative as shown in a formula 5 and a preparation method thereof as well as the application of a compound 5 of F as a PET imaging molecular probe. The compound has favorable suppressive activity of carbonic anhydrase, stronger hydrophilicity and little collection and little nonspecific absorption in a digestive system of a human body. The preparation method of the compound adopts simply and easily obtained raw materials and simple preparation method and has no particular requirements for high-temperature, high-pressure or sensitive reagents. The invention also discloses a intermediate compound as shown in a formula 4 used in the preparation method of the compound and the preparation method thereof.

Description

technical field [0001] The present invention relates to a kind of new compound and its preparation method and application, as well as its intermediate and the preparation method of intermediate, specifically relate to a kind of benzenesulfonamide compound and its preparation method and application, as well as its intermediate and the preparation of intermediate method. Background technique [0002] Tumor hypoxia is commonly found in a variety of solid tumors, and is considered to be one of the main factors leading to the failure of radiotherapy and chemotherapy. Tumor hypoxia will affect the efficacy of tumor radiotherapy. Therefore, it is necessary to find a reliable, non-invasive and convenient Tumor hypoxia detection technology has important practical significance and application value. Positron emission tomography (PET) is the most advanced non-invasive high-quality imaging diagnosis technology, which enables human beings to realize molecular level research in vivo for ...

Claims

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Application Information

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IPC IPC(8): C07D251/52A61K51/04A61K101/02
Inventor 张岚武明星郭飞虎施玲丽汪勇先尹端沚
Owner SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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