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Dihydroporphyrin derivatives and preparation method and application

A technology of chlorin and its derivatives, which is applied in the field of medicine, can solve problems such as limiting the structure and derivatization of chlorin, and achieve the effects of cheap and easy-to-obtain catalysts, high fluorescence quantum efficiency, and long absorption wavelengths

Active Publication Date: 2019-12-13
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a large amount of raw materials can be obtained from natural extraction to prepare chlorinated porphyrins, it severely limits the structure and derivatization of chlorinated chlorinated porphyrins, and the other two ways are the breakthroughs for everyone to find new chlorinated chlorinated derivatives

Method used

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  • Dihydroporphyrin derivatives and preparation method and application
  • Dihydroporphyrin derivatives and preparation method and application
  • Dihydroporphyrin derivatives and preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048]

[0049] Take a 50mL round bottom flask, dissolve 0.05mmol of 5,15-di-p-methylphenyl-2,3-dihydrozinc porphyrin (1a) and 0.27mmol of p-toluidine (1a) in freshly distilled In 30mL of dichloromethane solvent, place the round-bottomed flask at room temperature and stir, add NaAuCl to the reaction vessel 4 2H 2 O (0.08mmol), react for about 1min, until the reaction of 1a is complete, quench the reaction with a solution of sodium borohydride (0.26mmol) in methanol (2mL), stir at room temperature for half an hour, then extract with water and dichloromethane, until The aqueous layer becomes colorless, the organic phases are combined, dried with anhydrous potassium carbonate, filtered, rotary evaporated, and the solvent is removed to obtain a mixture containing 10, 10' bilateral amination, 20, 20' directly coupled compound 3a, and then The product 3a was separated and purified by column chromatography with a yield of 68%.

[0050] 1 H NMR (600MHz, CDCl 3 )δ8.85(d, J=4.8Hz...

Embodiment 2

[0052]

[0053] 1a and 2b were used as reactants, and the rest were the same as in Example 1 to obtain the product 10, the 20-position double-sided amination of 5a, with a yield of 60%.

[0054] 1 H NMR (600MHz, CDCl 3 )δ8.77(d, J=4.2Hz, 1H), 8.58(d, J=4.2Hz, 1H), 8.50(d, J=4.2Hz, 1H), 8.36(d, J=4.2Hz, 1H) ,8.31(d,J=4.2Hz,1H),8.02(d,J=4.2Hz,1H),7.89(d,J=7.2Hz,2H),7.67(d,J=5.4Hz,2H),7.44 (d,J=7.2Hz,4H),6.94(s,4H),6.62(s,4H),4.26(m,1H),4.12(m,3H),4.05(s,3H),3.82(s, 3H), 2.62(s,3H), 2.60(s,3H), 2.23(s,3H), 2.21(s,3H)ppm; HR-MS (MALDI) calculated value C 50 h 44 N 6 Zn[M]+792.2919, the actual value is 792.2918.

Embodiment 3

[0056]

[0057] 1a and 2c were used as reactants, and the rest were the same as in Example 1 to obtain product 5b with a yield of 45%.

[0058] 1 H NMR (600MHz, CDCl 3 )δ8.76(d, J=4.2Hz, 1H), 8.56(d, J=4.8Hz, 1H), 8.48(d, J=4.8Hz, 1H), 8.34(d, J=4.2Hz, 1H) ,8.29(d,J=4.2Hz,1H),8.01(d,J=4.8Hz,1H),7.88(m,2H),7.66(m,2H),7.43(m,4H),6.59(m, 6H),6.49(m,2H),4.21(m,1H),4.09(m,3H),4.03(s,3H),3.78(s,3H),3.56(s,3H),3.50(s,3H ), 2.62(s,3H), 2.58(s,3H)ppm; HR-MS(MALDI) calculated value [M]+C 50 h 44 N 6 o 2 Zn 824.2817, theoretical value 824.2818.

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Abstract

The invention relates to a dihydroporphyrin derivative and a preparation method and an application. The dihydroporphyrin is porphyrin hydrogenated at sites 2 and 3. The meso-N substituted dihydroporphyrin compound derivatization prepartaio method is simple and feasible, and the catalyst is cheap and easily available, so that the preparation method is an environment-friendly preparation method. According to the dihydroporphyrin derivative, by introducing nitrogen atoms into the molecular structure, the conjugated system of the target compound is further enhanced, and the target compound has a relatively long absorption wavelength and a relatively high fluorescence quantum yield. Through a phototoxic experiment, the applicant verifies that the dihydroporphyrin derivative has photosensitive activity and lays a solid foundation of being developed to a novel photosensitizer.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a chlorinated porphyrin derivative, a preparation method and an application thereof, in particular to a method for preparing a chlorinated porphyrin derivative by oxidation-controlled meso position-selective amination of chlorinated porphyrin. Background technique [0002] Tumor photodynamic therapy (Photodynamic Therapy, PDT) is an emerging minimally invasive or non-invasive treatment method for tumors. It kills tumor cells by administering a photosensitizer that has a selective aggregation effect on tumor tissue, and then irradiating the lesion with a light source of a specific wavelength to trigger photodynamic oxidative damage in the lesion. It has attracted people's attention because of its targeting, reproducibility and synergy. In the past two decades, PDT has been formally approved by the governments of various countries to enter the clinic, and has become a routine t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07D519/00A61K41/00A61P35/00
CPCA61K41/0071C07D487/22C07D519/00
Inventor 欧阳勤程琦陈应春
Owner ARMY MEDICAL UNIV
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