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Tetrathiol-porphyrin compound as well as preparation method and application thereof

A technology of tetramercaptoporphyrin and tetramercapto, applied in organic chemistry, drug combination, pharmaceutical formulations, etc., can solve the problems of poor stability, easy agglomeration, insoluble and water, etc., and achieve the effect of good dispersibility and stability

Inactive Publication Date: 2018-03-06
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the problems existing in the above-mentioned prior art, the object of the present invention is to provide a tetramercaptoporphyrin compound and its preparation method and application. The tetramercaptoporphyrin compound prepared by the method of the present invention has a strong coordination ability. The tetramercaptoporphyrin-modified metal-organic framework (UiO-66) prepared by combining the framework materials, that is, UiO-66-H 2 TPP-(SH) 4 , has very good water solubility, well overcomes the problems that porphyrin molecular compounds in the prior art are not easily soluble in water, easy to agglomerate, and poor in stability, so that the singlet oxygen of porphyrin and its derivatives Quantum yield, fluorescence lifetime, and photosensitivity have been greatly improved

Method used

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  • Tetrathiol-porphyrin compound as well as preparation method and application thereof
  • Tetrathiol-porphyrin compound as well as preparation method and application thereof
  • Tetrathiol-porphyrin compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Tetramercaptoporphyrin H 2 TPP-(SH) 4 Preparation of:

[0077] (1)H 2 TPP-(COOH) 4 Preparation of:

[0078] Methyl p-formylbenzoate (6.9g, 0.042mol) and 100mL propionic acid were heated to 145°C for reaction and reflux to obtain a mixed solution, then 20mL propionic acid and pyrrole (3.0mL, 0.043mol) were added dropwise to the above mixture After the dropwise addition, continue to reflux for 1h. Then, it was naturally cooled to room temperature, and methanol was added to stand for 12h. Finally, filter with suction, wash the filter cake with water and methanol, and obtain the purple powder H 2 TPP-(COOCH 3 ) 4 , its mass is 1.8 g, the amount of substance is 0.0021 mol, and the yield is 20%.

[0079] 1g H 2 TPP-(COOCH 3 ) 4 , 80mL tetrahydrofuran (THF) and 6mL 10mol L -1 KOH and 100mL water were heated to 70°C and refluxed for 6h, then naturally cooled to room temperature. THF was distilled off at atmospheric pressure and filtered. Then the filtrate was adj...

Embodiment 2

[0093] Tetramercaptoporphyrin H 2 TPP-(SH) 4 Preparation of:

[0094] (1)H 2 TPP-(COOH) 4 The preparation method is with embodiment 1.

[0095] (2)H 2 TPP-(SH) 4 Preparation of:

[0096] H 2 TPP-(COOH) 4 (90 mg, 0.11 mmol) was dissolved in 6 mL of dry dichloromethane, and then SOCl 2 (6mL, 0.069mol) was slowly added dropwise to the mixed solution, reacted at 45°C, refluxed for 5h, and evaporated excess SOCl under normal pressure 2 and dichloromethane to obtain tetraacylchlorophenylporphyrin H as a black-green solid 2 TPP-(COCl) 4 . 93mg H 2 TPP-(COCl) 4 Dissolve in 15 mL of dried THF to obtain the first reaction solution.

[0097] 1,2-Dimercaptoethane (672 μL, 8.0 mmol) and triethylamine (40 μL, 0.29 mmol) were dissolved in 25 mL of dry THF to obtain a second reaction solution.

[0098] The first reaction solution was added dropwise to the second reaction solution at room temperature and protected from light at a rate of 3 seconds / drop, and the reaction was sti...

Embodiment 3

[0101] Tetramercaptoporphyrin H 2 TPP-(SH) 4 Preparation of:

[0102] (1)H 2 TPP-(COOH) 4 The preparation method is with embodiment 1.

[0103] (2)H 2 TPP-(SH) 4 Preparation of:

[0104] H 2 TPP-(COOH) 4 (79 mg, 0.10 mmol) was dissolved in 4 mL of dry dichloromethane, and then SOCl 2 (4mL, 0.069mol) was slowly added dropwise to the mixed solution, and after reflux at 43°C for 4.5h, the excess SOCl was distilled off under normal pressure 2 and dichloromethane to obtain tetraacylchlorophenylporphyrin H as a black-green solid 2 TPP-(COCl) 4 . 83mg H 2 TPP-(COCl) 4 Dissolve in 15 mL of dried THF to obtain the first reaction solution.

[0105] 1,2-Dimercaptoethane (504 μL, 6.0 mmol) and triethylamine (40 μL, 0.29 mmol) were dissolved in 13 mL of dry THF to obtain a second reaction solution.

[0106] The first reaction solution was added dropwise to the second reaction solution at room temperature and protected from light at a rate of 3 seconds / drop, and the reaction...

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Abstract

The invention relates to the field of functional coordination compounds and in particular relates to a tetrathiol-porphyrin compound as well as a preparation method and application thereof. Tetrathiol-porphyrin prepared by the method disclosed by the invention has strong coordination ability; when tetrathiol-porphyrin is combined with a UiO-66 framework material, a metal-organic framework material(UiO-66) modified with tetrathiol-porphyrin, namely UiO-66-H2TPP-(SH)4, has excellent water solubility, and the problems existing in the prior art that porphyrin molecular compounds are difficultly dissolved in water and are easy to aggregate and poor in stability are well solved, so that the quantum yield of singlet oxygen, fluorescence lifetime and light sensitive characteristics of porphyrin and derivatives thereof are greatly improved.

Description

technical field [0001] The invention relates to the field of functional complexes, in particular to a tetramercaptoporphyrin compound and its preparation method and application. Background technique [0002] Porphyrin and its derivatives are typical planar π-conjugated macrocyclic molecules, which widely exist in nature and living organisms. As the core part of the compound, the porphyrin ring is composed of a closed and continuous conjugated porphyrin ring formed by connecting four pyrrole rings through methine (-CH=). The periphery of the porphyrin ring can be substituted by various functional groups to form a variety of substituted porphyrins. In porphyrins that exist in nature, the hydrogen on the conjugated porphine ring is usually replaced by other functional groups, while the artificial porphyrins are mainly replaced by four methine groups, that is, the meso-position (middle position). Due to the high synthesis yield and good stability of meso-position (middle posit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C07D487/22A61K41/00A61P35/00
CPCA61K41/0076C07D487/22C08G83/008
Inventor 董育斌姜嫄阚京兰
Owner SHANDONG NORMAL UNIV
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