Water-soluble carboxyl N-dislocation porphyrin as well as preparation method and application thereof
A water-soluble, porphyrin-based technology, applied in pharmaceutical formulations, medical preparations containing active ingredients, organic chemistry, etc., can solve the harmful effects of human tissue and achieve the effect of reducing burns
Pending Publication Date: 2021-08-27
YICHUN UNIVERSITY
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[0003] At present, porphyrin is mainly used as a photosensitizer for cancer treatment. Through clinical research, it has been found that the light required by the existing photosensitizer is 650nm, but the light of 650nm is harmful to human tissues.
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Embodiment 1
[0049] refer to Figure 1-2 , Step 1: Synthesis of methyl benzoate group substituted N-dislocation porphyrin
[0050] S1: Take a 1000mL reactor, add 500mL dichloromethane, 5mmoL pyrrole and 5mmoL methyl 4-formylbenzoate in sequence, and add 3.5mmoL methanesulfonic acid after magnetic stirring to dissolve;
[0051] S2: After stirring for 30 minutes at room temperature, add 14mmol of triethylamine and stir for 1 minute, then add 5mmol of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), stir and react for one hour, then rotate Evaporation to a small amount of solvent remained followed by chromatography on alumina and filtration to obtain a solid product.
[0052]Step 2: Separation and detection of methyl benzoate substituted N-dislocation porphyrin
[0053] S3: After soaking 20g of alumina for chromatography with an appropriate amount of n-hexane and stirring evenly, add it to the chromatography column in stages to a height of about 9cm;
[0054] S4: Dissolve the solid product...
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The invention discloses water-soluble carboxyl N-dislocation porphyrin as well as a preparation method and application thereof, and relates to the technical field of porphyrin synthesis. The molecular formula of the water-soluble carboxyl N-dislocated porphyrin is C48H30N4O8; and the preparation method comprises the following steps: reacting an alkali solution of methyl benzoate substituted N-dislocation porphyrin in a mixed solution of methanol and tetrahydrofuran at 60-80 DEG C for 12-24 hours, removing an organic solvent, adjusting the pH value to 3, filtering, and drying to obtain the water-soluble carboxyl N-dislocation porphyrin. According to the method, the yield of the synthesis reaction of the water-soluble carboxylic acid N-dislocation porphyrin is calculated through the liquid chromatograph-mass spectrometer, and the optimal process condition is obtained by adopting a single-factor experiment and an orthogonal experiment, so that the yield of the water-soluble carboxylic acid N-dislocation porphyrin can reach 95% or above.
Description
technical field [0001] The invention relates to the technical field of porphyrin synthesis, in particular to a water-soluble carboxyl N-dislocation porphyrin and its preparation method and application. Background technique [0002] Porphyrin is a highly conjugated system containing 18 π electrons. In recent years, porphyrin compounds have been widely used in medical and industrial fields due to their large surface area and easy modification. N-dislocation porphyrin is an isomer of porphyrin, which is a cyclic compound with a conjugated structure of 18 π electrons. Compared with ordinary porphyrin molecules, N-misplaced porphyrins have lower symmetry, higher reactivity, and unique tautomerism due to one of the pyrrole rings of N-misplaced porphyrins being flipped outwards . Compared with porphyrin molecule, N-dislocation porphyrin has wider application prospect. [0003] At present, porphyrin is mainly used as a photosensitizer for cancer treatment. It has been found thro...
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IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCC07D487/22A61K41/0076A61P35/00
Inventor 彭素红张秋雨李文姝徐文浩晋霄鹏凌允华谭少魁陈雨晴李管琳杨喜恒王新陈璐娄喻李蔡莎莎肖慧庆赵欣彤
Owner YICHUN UNIVERSITY