Synthesis and application of photosensitizer

A compound and alkyl technology, which is applied in the synthesis of biologically active molecules or pharmaceutical intermediates, can solve the problems of limiting the effect of photosensitizers and reducing the efficiency of singlet oxygen generation, and achieve the goal of simplifying the post-processing process and improving the utilization rate of photosensitizers Effect

Active Publication Date: 2020-09-15
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional photosensitizers are easy to aggregate through π-π stacking, which causes fluorescence quenching and reduces the si

Method used

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  • Synthesis and application of photosensitizer
  • Synthesis and application of photosensitizer
  • Synthesis and application of photosensitizer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] (1) Synthesis of compound 3

[0033] Compound 1 (500mg, 0.83mmol), compound 2 (538mg, 1.21mmol), potassium carbonate (2.5M in H 2 (20, 4mL) was added to tetrahydrofuran, tetrakistriphenylphosphine palladium (80mg) was added under nitrogen protection, and reacted at 60°C for 12 hours. The organic layer was extracted, dried, concentrated, and silica gel column chromatography to obtain compound 3 (560mg, 80.5% ). HRMS calcd.for C 51 h 44 N 3 o 5 S 2 [M+H] + 842.2717, found 842.2730; 1 H NMR (500MHz, CDCl 3 )δ8.10(d, J=8.0Hz, 2H), 8.01(d, J=8.0Hz, 2H), 7.85-7.77(m, 4H), 7.60(d, J=3.5Hz, 1H), 7.21( d,J=8.0Hz,2H),7.17-7.08(m,5H),7.07-7.00(m,3H),6.97(d,J=8.5Hz,2H),6.68(d,J=8.5Hz,2H ),6.65(d,J=8.5Hz,2H),5.11(t,J=6.0Hz,1H),4.55(d,J=4.5Hz,2H),3.75(s,3H),3.74(s,3H ),1.49(s,9H); 13 C NMR (126MHz, CDCl 3 )δ187.4, 158.2, 158.1, 155.5, 153.9 (2C), 152.4, 144.7, 144.1, 142.5, 141.2, 140.8, 138.7, 137.4, 136.2, 135.1, 134.6, 133.8, 132.6 (5C), 1391.6, 13 ,129.2...

Embodiment 2

[0043]

[0044] (1) Synthesis of compound V-4

[0045] Compound V-2 (50mg, 0.05mmoL) and HBTU (38mg, 0.10mmoL) were dissolved in 5mL of dichloromethane, added DIEA (36μL, 0.20mmoL) and stirred at room temperature for 10min, then added N-(2-aminoethyl)malein Imide trifluoroacetate (20mg, 0.08mmoL) was reacted at room temperature for 2h. The reaction solution was extracted with dichloromethane, dried, concentrated, and column chromatographed to obtain compound V-4 (46 mg, 82%). HRMS calcd.for C 63 h 51 N 10 o 6 S 2 [M+H] + 1107.3435,found 1107.3456; 1 H NMR (500MHz, CDCl 3 )δ8.14(d, J=7.5Hz, 2H), 7.86(d, J=7.5Hz, 1H), 7.83-7.76(m, 3H), 7.68-7.55(m, 4H), 7.38(s, 1H ),7.20(d,J=7.5Hz,2H),7.17-7.08(m,5H),7.06-7.00(m,3H),6.97(d,J=8.0Hz,2H),6.73-6.62(m, 6H),6.44(s,1H),4.70-4.58(m,4H),3.75(s,3H),3.75(s,3H),3.64(m,2H),3.41(m,2H),3.09(m ,2H),2.79(m,4H).

[0046] (2) Synthesis of compound V-5

[0047] Intermediate V-4 (20mg, 0.018mmoL) was dissolved in DMSO (0.5mL), peptid...

Embodiment 3

[0049]

[0050] Compound V-3 (15mg), compound 5 (100mg, 0.61mmol) was added to acetonitrile (20mL), oxygen was introduced into the reaction solution, light was irradiated for 3 hours (300W, PerfectLight, China), TLC was monitored and filtered after the reaction was completed. The solid compound V-3 was continued to be used in the next photocatalytic oxidation reaction, and the reaction solution was concentrated under reduced pressure to obtain compound 6, which was directly used for NMR determination. HRMS calcd.for C 11 h 17 o 3 [M+H] + 197.1172, found 197.1157; 1 H NMR (300MHz, CDCl 3 )δ8.56(m,1H),6.76(s,1H),5.24(s,1H),5.08(s,1H),4.53(m,1H),2.90-1.83(m,5H),1.77(s ,3H),1.40-1.20(m,3H); 13 C NMR (75MHz, CDCl 3 )δ200.3, 200.1, 151.0, 150.9, 145.2, 145.0, 135.4, 135.3, 112.4, 112.0, 83.2, 83.0, 44.0, 43.8, 37.6, 37.4, 32.6, 32.5, 18.2, 18.0, 15.6.

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Abstract

The invention relates to the field of organic synthesis and biological medicine, particularly to synthesis of a class of photosensitizers with aggregation-induced emission properties, and applicationof the photosensitizers loaded on a solid-phase material in synthesis of bioactive molecules or medical intermediates and application of the photosensitizers in the medical fields of photodynamic therapy, immunogenic cell death and the like. According to the invention, the photosensitizer can effectively generate singlet oxygen under an illumination condition; compared with the traditional photosensitizer, the photosensitizer of the invention has the following characteristics that the phenomena of aggregation fluorescence quenching and aggregation singlet oxygen generation capacity reduction are avoided; and when the photosensitizer is applied to synthesis of bioactive molecules or medical intermediates, the photosensitizer has the advantages of reusability, simple and convenient post-treatment and the like, and the characteristics are not possessed by traditional photosensitizers.

Description

technical field [0001] The present invention relates to the fields of organic synthesis and biomedicine, and specifically refers to the discovery and synthesis of a class of photosensitizers with aggregation-induced luminescent properties, and the loading of such photosensitizers on solid-phase materials for the production of bioactive molecules or pharmaceutical intermediates. Synthesis; meanwhile, the photosensitizer can also be used in medical fields such as photodynamic therapy and immunogenic cell death. Background technique [0002] singlet oxygen ( 1 o 2 ) is an excited state of oxygen molecules and is an important active oxygen molecule. Due to its high activity, it has broad applications in many fields of physics, chemistry, environment and biomedicine. In organic synthesis, singlet oxygen can react with monoolefins to generate dioxacycloalkanes or hydrocarbon peroxides; it can also undergo Diels-Alder addition reactions with conjugated π bonds to generate intern...

Claims

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Application Information

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IPC IPC(8): C07D417/10C07D417/14C09K11/06A61K41/00A61P35/00C07K5/09C07K5/11C07K7/06
CPCC07D417/10C07D417/14C09K11/06A61K41/0057A61P35/00C07K5/1019C07K5/0817C07K7/06C09K2211/1007C09K2211/1051C09K2211/1092C09K2211/1029C09K2211/1059
Inventor 张崇敬杜恩明
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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