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Dendrimer containing 5-aminolevulinic acid and 3-hydroxypyridone, its preparation method and use

A technology of aminolevulinic acid and hydroxypyridine, applied in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve problems that have not been reported

Active Publication Date: 2018-04-20
ZHEJIANG GONGSHANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no report about the research on the dendrimer compound containing ALA and iron chelating agent simultaneously

Method used

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  • Dendrimer containing 5-aminolevulinic acid and 3-hydroxypyridone, its preparation method and use
  • Dendrimer containing 5-aminolevulinic acid and 3-hydroxypyridone, its preparation method and use
  • Dendrimer containing 5-aminolevulinic acid and 3-hydroxypyridone, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, the preparation of dendrimer 10a

[0040] Its synthetic route is shown in Scheme 1:

[0041]

[0042] Its concrete preparation method, carries out following steps successively:

[0043] Tris(3-acetoxypropyl)nitromethane (2): Methylnitrotripropanol (1) (10g, 42mmol) was dissolved in pyridine (50mL), acetic anhydride (25mL) was added, and the mixture was stirred at room temperature for 18h . 50 mL of water was added to the reaction liquid, stirred for 30 min, and then concentrated to about half volume. Dichloromethane (DCM, 100mL) was added to the residual liquid, followed by 5% Na 2 CO 3 The solution (50 mL) was washed with water (50 mL). After drying over anhydrous sodium sulfate, the solution was concentrated to dryness to obtain oily product 2 (14.2 g, 95% yield). 1 H NMR (CDCl 3 ,270MHz)δ:1.53(m,6H,3CH 2 ),1.97(m,6H,3CH 2 ),2.02(s,9H,3COCH 3 ),4.03(m,6H,3CH 2 ); ESI-MS: m / z 362 ([M+H] + ),384([M+Na] + ).

[0044] Three (3-acetoxypropyl) n...

Embodiment 2

[0053] Embodiment 2, the preparation of dendrimer 20a

[0054] Its synthetic route is shown in Scheme2:

[0055]

[0056] Its concrete preparation method, carries out following steps successively:

[0057] Compound 13: Fmoc-β-alanine (2.21g, 7.1mmol), 4-(2-(tert-butoxycarbonyl)ethyl)-4-aminopimelic acid di-tert-butyl ester (amine 12, 3.35g, 8.5mmol), HOBt (1.3g, 8.5mmol), DCC (1.71g, 8.5mmol) were dissolved in anhydrous DMF (30mL), and the mixture was stirred at room temperature overnight. Filtration, the filtrate was concentrated, and the residue was separated and purified by silica gel column chromatography (ethyl acetate / cyclohexane 1:1, V / V), and R f The eluent was 0.42, and the solvent was removed to give the product 13 as a white solid (4.64 g, 92% yield). 1 H NMR (CDCl 3 ,500MHz)δ1.43(s,27H,CH 3 ),1.98(m,6H,CH 2 ),2.21(m,6H,CH 2 ),2.35(m,2H,CH 2 ),3.48(m,2H,CH 2 ),4.21(m,1H,CH),4.35(m,2H,CH 2 ),5.70(br,1H,NH),6.05(s,1H,NH),7.31(m,2H,Ar),7.39(m,2H,Ar),7.60(d...

Embodiment 3

[0066] Embodiment 3, the preparation of dendrimer 25a

[0067] Its synthetic route is shown in Scheme 3:

[0068]

[0069] Its concrete preparation method, carries out following steps successively:

[0070] Compound 21: N-Cbz-L-phenylalanine (10mmol), ALA methyl ester hydrochloride (12mmol), DCC (10mmol), HOBt (10mmol) and [Bmim]Br (10mmol) were dissolved in THF (100mL ). The mixture was stirred at room temperature for 2 hours under nitrogen protection, and then cooled to 0 °C. Diisopropylethylamine (DIPEA) (12 mmol dissolved in 10 mL THF) was added dropwise to the above mixture, and stirred overnight at room temperature. Acetone (100 mL) was added, the precipitate was removed by filtration, and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane (100 mL), washed successively with 5% dilute hydrochloric acid, saturated sodium bicarbonate and water. It was dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to ...

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Abstract

The invention discloses a dendrimer compound containing 5-aminolevulinic acid and 3-hydroxypyridin-4-one, which has the following general structural formula: in the general formula, m≥3 and n≥1. The present invention also discloses the preparation method and application of the above-mentioned dendrimer: it can be used for the preparation of photodynamic therapy drugs, for example, for the preparation and treatment of basal cell carcinoma, squamous cell carcinoma, skin cancer, lung cancer, condyloma acuminatum, breast cancer, Photodynamic therapy agents for oral epidermoid carcinoma.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and relates to a class of dendrimer containing two functional groups of 5-aminolevulinic acid (ALA) and 3-hydroxypyridin-4-one (HPO), its preparation method and application---- As a photodynamic therapy drug. Background technique [0002] Photodynamic therapy (PDT) is a new technology for selective treatment of (vascular) proliferative lesions that came out in the late 1970s, and has become one of the most active research fields in the world's tumor prevention and treatment science. PDT is a new disease treatment method based on the interaction of light, photosensitizer and oxygen; the photosensitizer (photodynamic therapy drug) is injected into the human body, and after a certain period of time, the tumor site is irradiated with light of a specific wavelength. A series of photochemical and photobiological reactions, with the participation of molecular oxygen, produces singlet oxygen and / or free...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/69A61K31/4412A61K31/444A61P35/00A61K41/00
CPCY02P20/55
Inventor 周涛思南·贝托罗伯特·海德亚力山大·麦克罗伯特
Owner ZHEJIANG GONGSHANG UNIVERSITY
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