Tailed porphyrin compound modified by N1-substituted 3, 4-dihydropyrimidine-2-ketone and preparation method thereof

A technology of porphyrin compound and dihydropyrimidine, which is applied in the field of new photosensitizer and preparation, and achieves the effects of easy raw materials, simple synthesis method and mild reaction conditions

Inactive Publication Date: 2012-11-21
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no relevant research on introducing it into porphyrin molecules

Method used

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  • Tailed porphyrin compound modified by N1-substituted 3, 4-dihydropyrimidine-2-ketone and preparation method thereof
  • Tailed porphyrin compound modified by N1-substituted 3, 4-dihydropyrimidine-2-ketone and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] a. Weigh 5-p-hydroxyphenyl-10,15,20-triphenylporphyrin (0.63g, 1.0mmol) in a round bottom flask, add N,N-dimethylformamide (8.0mL, 0.1mol ), so that it just dissolves completely;

[0021] b. Add N1-(4-bromobutyl)-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-one (2.0mmol ,0.79g), 5.0g of anhydrous potassium carbonate and 40mL of acetone, stirred at room temperature for 15 hours, TLC traced the complete reaction;

[0022] c. After that, the acetone was evaporated under reduced pressure, and then distilled water was added. After filtering and drying, column chromatography was performed with 300-400 mesh silica gel. First use the mixed solvent of dichloromethane and sherwood oil with a volume ratio of 2.5:1 as the eluent to elute the monohydroxyporphyrin, and then use a mixed solvent of ethyl acetate and sherwood oil with a volume ratio of 1:5 to carry out Elution, collect the third point. After precipitation and drying, a purple solid was obtained with a yi...

Embodiment 2

[0026] Using substantially the same process as in Example 1, the raw material was changed to N1-(4-bromopentyl)-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-one , the dosage was 2.5 mmol, and a purple solid was obtained with a yield of 85%.

[0027] The spectral characterization data of the product are as follows: 1 H NMR (CDCl 3 ,500MHz)δ:-2.74(s,2H,pyrrole-NH),1.17(t,3H,J=7.5Hz,ester-CH 3 ),1.58-1.97(m,6H,3×CH 2 ),2.59(s,3H,CH 3 ),3.67-3.73(m,1H,NCH 2 ),3.99-4.05(m,1H,NCH 2 ),4.11(q,2H,J=7Hz,OCH 2 ), 4.17(t,2H,J=6Hz,ester-CH 2 ),5.39(s,1H,CH),5.56(br s,1H,NH,exchanged with D 2 O),7.23(d,2H,J=8.5Hz,5-phenyl),7.27-7.34(m,5H,DHPM-phenyl),7.71-7.74(m,9H,phenyl),8.10(d,2H,5 -phenyl), 8.21 (d, 6H, phenyl), 8.84 (s, 6H, β-pyrrole), 8.89 ((s, 2H, β-pyrrole)). 13 C NMR (126MHz, CDCl 3)δ:166.21,158.92,153.64,148.69,143.54,142.28,135.65,134.60,134.49,128.77,127.92,127.72,126.70,126.33,120.19,120.11,119.99,112.77,104.78,99.99,67.99,60.27,54.16,42.70 , 29.77, 29....

Embodiment 3

[0029] Using substantially the same process as in Example 1, the raw material was changed to N1-(4-bromohexyl)-4-phenyl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-one, The dosage was 2.5 mmol, and a purple solid was obtained with a yield of 83%.

[0030] The spectral data of the product are as follows: 1 H NMR (CDCl 3 ,500MHz)δ:-2.74(s,2H,pyrrole-NH),1.16(t,3H,J=7Hz,ester-CH 3 ),1.59-1.93(m,8H,4×CH 2 ),2.58(s,3H,CH 3 ),3.62-3.67(m,1H,NCH 2 ),3.96-3.99(m,1H,NCH 2 ),4.09(q,2H,J=7Hz,OCH 2 ), 4.18(t,2H,J=6Hz,ester-CH 2 ),5.38(s,1H,CH),5.56(br s,1H,NH,exchangedwith D 2 O),7.22(d,2H,J=5Hz,5-phenyl),7.26-7.32(m,5H,DHPM-phenyl),7.72(br,9H,phenyl),8.09(d,2H,5-phenyl) , 8.21 (br, 6H, phenyl), 8.84 (s, 6H, β-pyrrole), 8.88 ((s, 2H, β-pyrrole)). 13 C NMR (126MHz, CDCl 3 )δ:166.21,158.98,153.53,148.74,143.55,142.29,135.65,134.60,134.44,128.75,127.90,127.71,126.70,126.33,120.23,120.11,119.98,112.77,104.71,68.08,60.24,54.15,42.72,29.92 , 29.45, 26.97, 26.72, 26.05, 16.24, 1...

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Abstract

The invention provides a tailed porphyrin compound modified by N1-substituted 3, 4-dihydropyrimidine-2-ketone and a preparation method thereof. N1-substituted 3, 4-dihydropyrimidine-2-ketone small molecular compounds with biological activity are introduced to porphyrin molecules to form the novel porphyrin compound. The preparation method includes: fully dissolving monohydroxy porphyrin, adding the N1-substituted 3, 4-dihydropyrimidine-2-ketone, anhydrous potassium carbonate and acetone, and stirring at normal temperature; and removing the acetone after full reaction, adding water, filtering, drying and separating to obtain the tailed porphyrin compound. The tailed porphyrin compound modified by N1-substituted 3, 4-dihydropyrimidine-2-ketone prepared by the method can be easily dissolved in the acetone, so that use of the porphyrin compound is facilitated. The preparation method is simple, mild in reaction conditions, easy in raw material recycling, and simple and safe to operate, and accordingly a production method of novel photosensitizers is provided for photodynamic therapies.

Description

technical field [0001] The invention relates to a novel photosensitizer for medicine and a preparation method, in particular to a modified tail porphyrin compound and a preparation method. Background technique [0002] Porphyrins is a general term for homologues and derivatives with substituents on the outer ring of porphine. Porphine is a planar molecule with a large π system composed of 18 atoms and 18 electrons, and has aromaticity. Due to the existence of the large π-conjugated skeleton, porphyrin compounds have strong absorption in the ultraviolet-visible region. Studies have shown that porphyrin can not only absorb visible light energy, but also has good sensitivity to light. Due to these properties of porphyrins, they are widely used as photosensitizers in photodynamic therapy, and most of the photosensitizers that have been approved for use and are being clinically tested are porphyrin compounds. At present, one of the research hotspots of porphyrin-based photosen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00
Inventor 曾荣今沈鹏飞刘传磊唐沙
Owner HUNAN UNIV OF SCI & TECH
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