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Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof

A kind of technology of tetraphenyl porphyrin and compound, applied in beta-substituted porphyrin derivatives and the fields of preparation and application thereof, achieving the effects of low cost, mild reaction conditions and good application prospects

Inactive Publication Date: 2017-02-01
WUHAN INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof
  • Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof
  • Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof

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Embodiment 1

[0057] The preparation of β-(2,3-dihydro-naphtho[1,2,e]-m-oxazine) tetraphenylcopper porphyrin, concrete steps are as follows:

[0058] 1. Preparation of 5,10,15,20-tetraphenylporphyrin: In a 250mL three-necked flask equipped with a reflux condenser, add 10.600g (0.1mol) of benzaldehyde and 110mL of propionic acid, and heat to slightly Reflux (about 135°C), and slowly add 6.700g (0.1mol, 7mL) of pyrrole and 25mL of propionic acid mixture dropwise (30min to complete the dropwise addition). Stirring and reflux were continued for 1.5 h at 135°C. Cool down naturally and let stand overnight. After suction filtration, the solid was washed with ethanol until the filtrate was colorless, and dried in vacuo to obtain 2.24 g of the crude product as bright purple crystal 5,10,15,20-tetraphenylporphyrin, with a yield of 14.6%.

[0059] 2. Preparation of 5,10,15,20-tetraphenyl copper porphyrin: In a 250mL round bottom flask equipped with a reflux condenser, add 1.000g (1.6mmol) 5,10,15,20...

Embodiment 2

[0066]The preparation of β-(2,3-dihydro-naphthalene [1,2, e]-m-oxazine) tetraphenyl zinc porphyrin, concrete steps are with embodiment 1, just carry out following adjustment:

[0067] 1) Replace the copper acetate in step 6 with 0.117g (0.64mmol) of zinc acetate, and react β-amino-5,10,15,20-tetraphenylporphyrin with zinc acetate to prepare β-amino-5 , 10,15,20-tetraphenyl zinc porphyrin 0.202g, yield 95%;

[0068] 2) Replace the β-amino-5,10,15,20-tetraphenyl copper porphyrin in step 7 with 0.050g (0.072mmol ), make it react with formaldehyde and 2-naphthol, obtain β-(2,3-dihydro-naphthalene [1,2, e]-m-oxazine) tetraphenyl zinc porphyrin 0.024g, productive rate 38.5%.

Embodiment 3

[0070] The preparation of β-(2,3-dihydro-naphthalene[1,2,e]-m-oxazine) tetraphenylporphyrin, concrete steps are as follows:

[0071] Weigh 0.060g of the final product β-(2,3-dihydro-naphthalene[1,2,e]-m-oxazine)tetraphenylcopper porphyrin prepared in Example 1 and place it in a 50mL single-necked bottle , add 20 mL of chloroform, stir to dissolve at room temperature, add 1 mL of concentrated sulfuric acid, stir for 5 min, pour it into 50 mL of ice-water mixture, add sodium hydroxide solution to neutralize to neutral, wash with water, add anhydrous sodium sulfate to dry. Suction filtration, concentration to saturation, adding hot methanol for recrystallization to obtain 0.046 g of β-(2,3-dihydro-naphtho[1,2,e]-m-oxazine) tetraphenylporphyrin, yield 82% . The infrared spectrum of the obtained target product β-(2,3-dihydro-naphthalene[1,2,e]-m-oxazine) tetraphenylporphyrin is shown in Figure 9 .

[0072] The main product in embodiment 1 and the ultraviolet-visible spectrogram...

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Abstract

The invention discloses beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin of which the structural general formula is disclosed as Formula (I) or Formula (II), and a preparation method and application thereof. The preparation method comprises the following steps: 1) preparing 5,10,15,20-tetraphenyl porphyrin from pyrrole and benzaldehyde, carrying out coordination with copper to obtain 5,10,15,20-tetraphenyl copper porphyrins, carrying out regioselective nitration to obtain beta-nitro-substituted-5,10,15,20-tetraphenyl copper porphyrins, carrying out decoppering and reduction to obtain beta-amino-substituted-5,10,15,20-tetraphenyl porphyrins, and reacting with acetate to obtain beta-amino-substituted-tetraphenyl metalloporphyrins (beta-NH2-MTPP); 2) carrying out condensation reaction on the beta-NH2-MTPP, formaldehyde and 2-naphthol, separating the product by column chromatography to obtain a beta-(2,3-dihydro-1H-naphthyl[1,2,e]-m-oxazinyl)-substituted tetraphenyl porphyrin metal complex; and decoppering to obtain the beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin. The compounds can be used for preparing photodynamic-therapy photosensitizers and antineoplastic drugs with small toxic and side effects and high activity.

Description

[0001] Technical field: [0002] The present invention relates to β-substituted porphyrin derivatives and their preparation and application fields, in particular to β-(2,3-dihydro-naphtho[1,2,e]-m-oxazine) tetraphenylporphyrin Compound, preparation method and application in the field of antitumor drugs. [0003] Background technique: [0004] Porphyrins are a special class of conjugated macrocyclic compounds containing 18 π electrons. Porphyrin compounds are approved as photosensitizers for treating various types of tumors because they can excite singlet oxygen or form active oxygen compounds and deliver them to tumor tissues to treat tumors. In recent years, the research focus of porphyrin photosensitizers has shifted to β-position modification. Due to the three-dimensional interaction between the β-position substituent of pyrrole and the middle-position substituent in the porphyrin molecule, the porphyrin macromolecule tends to be non-planar, thus presenting many new spectr...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/536A61P35/00A61K41/00
CPCA61K41/0076C07D487/22
Inventor 高洪王慧东陈楚珺黄齐茂
Owner WUHAN INSTITUTE OF TECHNOLOGY
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