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Endoperoxide of controlled release singlet oxygen and preparation method and application thereof

A technology of singlet oxygen and peroxide, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of low conversion rate, endoperoxide decomposition, conversion rate reduction, etc., and achieve high conversion rate and broad The effect of applying the foreground

Active Publication Date: 2018-08-28
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In 1956, Schenck and Dunlap reported the use of ethanol as a solvent to oxidize the substrate with oxygen under the action of light and rose red at -100 °C to prepare endoperoxides. However, the reaction required a temperature of -100 °C. The conditions are not easy to realize and control
[0006] In September 2006, David Costa's research team used sodium molybdate to catalyze hydrogen peroxide to prepare endoperoxide, but the conversion rate of this method was low and unstable
[0007] In January 2015, the research team of Prof. Dr. T. Linker irradiated the photosensitizer with a high-power LED lamp (400w), oxidized the substrate, and prepared endoperoxide. However, this method produced serious heat, resulting in endoperoxidation. Decomposition, lower conversion rate

Method used

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  • Endoperoxide of controlled release singlet oxygen and preparation method and application thereof
  • Endoperoxide of controlled release singlet oxygen and preparation method and application thereof
  • Endoperoxide of controlled release singlet oxygen and preparation method and application thereof

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Embodiment 1

[0033] Preparation of pyridine ring endoperoxide

[0034] Using 1,4-bis(bromomethyl)benzene as the original raw material, 1-(azidomethyl)-4(bromomethyl)benzene and 1-(4-( Azidomethyl) benzyl) pyridone two intermediates. The 1-(4-(azidomethyl)benzyl)pyridone intermediate is irradiated with laser light, and a 1,4-addition reaction occurs to obtain a compound with an endo-peroxide bridge, that is, a pyridine ring endoperoxide.

[0035] Specific steps are as follows:

[0036] 1) Add 1,4-bis(bromomethyl)benzene (1.218g, 4.614mmol) and sodium azide (0.3019g, 4.644mmol) into a 100mL round bottom flask, then add 10mL to the mixture to remove water The final DMF was stirred at room temperature for 12 hours; then the reaction process was detected with a thin-layer chromatography silica gel plate, and the reaction reached the maximum, and the reaction was stopped, and the DMF was removed by rotary evaporation on a rotary evaporator to obtain a colorless oily crude product, and then add...

Embodiment 2

[0040] The pyridine ring endoperoxide undergoes a click reaction with the small molecule target drug erlotinib to obtain a novel compound of the erlotinib-pyridine ring endoperoxide type.

[0041] Specific steps are as follows:

[0042] Add about 2mL of acetic acid to the Y2-1 (0.2000 g, 0.7346mmol) system to neutralize the remaining methylene blue in the system, add Erlotinib (0.2981g, 0.7577mmol) to the mixed system, add a small amount of copper sulfate pentahydrate CuSO 4 ·5H 2 O and sodium ascorbate are used as catalysts, the solvent is 8mL tetrahydrofuran (THF), 2mL water, 4mL ethanol, THF dissolves organic matter, water dissolves inorganic salt catalyst, tert-butanol is used to mix THF and water to avoid stratification to make it the same system. Set the temperature of the low-temperature reaction bath to 3°C, react for 12 hours, and then point the plate to detect the reaction progress. When the reaction reaches the maximum, stop the reaction, and distill under reduced ...

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Abstract

The invention discloses endoperoxide of controlled release singlet oxygen and a preparation method and application thereof. The endoperoxide takes 1, 4-di (bromomethyl) benzene as an original raw material, and 1-(nitrine methyl)-4 (bromomethyl) benzene and 1-(4-(nitrine methyl) benzyl) pyridine are obtained through the affinity substitution and affinity addition reaction. Lasers are used for irradiating the 1-(4-(nitrine methyl) benzyl) pyridine, a compound having endoperoxide bridged bond is obtained through 1, 4-addition reaction, the compound is known as pyridine ring endoperoxide for short. The pyridine ring endoperoxide and small molecular target medicines are subjected to click reaction to obtain a novel compound, namely, small molecular target-pyridine ring endoperoxide. The novel compound can control IO2 release, and can be applied to the fields of cancer treatment and environment science application study. The application prospect of the pyridine ring endoperoxide is expanded.

Description

technical field [0001] The invention belongs to the field of design, synthesis and application of organic compounds, and in particular relates to an endoperoxide for controlled release of singlet oxygen and its preparation and application. Background technique [0002] Endoperoxide (Endoperoxide) has an internal peroxygen bridge bond. Under certain conditions, the peroxygen bridge bond is broken to produce singlet oxygen ( 1 o 2 ). [0003] singlet oxygen ( 1 o 2 ) is a reactive form of oxygen molecules, 1 o 2 It is a strong oxidant with strong biological activity, and it is an important factor that causes cell membrane damage and promotes cell apoptosis. 1 o 2 Can react with many biomolecules, including DNA, lipids, free amino acids and proteins, etc. 1 o 2 It can also penetrate mitochondrial membranes or nucleic acids, causing DNA damage. 1 o 2 It can react with residues of cysteine, histidine, tryptophan, methionine and tyrosine, etc. 1 o 2 It can also cause ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/08A61P35/00
CPCA61P35/00C07D498/08
Inventor 薛金萍李冬瑶霍蓓蓓
Owner FUZHOU UNIV
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