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Dihydroporphin compound as well as preparation method and application thereof

A compound and hydrate technology, applied in the field of medicine, can solve the problems of uncontrollable quality, different physiological activities, unclear configuration, etc., and achieve the effects of less toxic and side effects, good safety and good application prospects.

Active Publication Date: 2021-10-01
SOUTHWEST JIAOTONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008]However, in the structure of compound HPPH and 2-(1-n-hexyloxy)ethyl chlorin f sodium salt, the 1' position is an asymmetric carbon, which is an external Racemic compounds, because the efficacy and toxicity of drugs are closely related to their three-dimensional configuration, the two enantiomers of racemic drugs are often absorbed in different ways in the body, thus showing different physiological activities. The configuration is not clear, resulting in uncontrollable quality

Method used

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  • Dihydroporphin compound as well as preparation method and application thereof
  • Dihydroporphin compound as well as preparation method and application thereof
  • Dihydroporphin compound as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0106] The preparation of embodiment 1,3-hexyloxymethyl-3-devinyl chlorin e4

[0107] (1) Synthesis of chlorin e4 dimethyl ester

[0108] Weigh 10.0g (18.12mmol) of chlorin e4 (CAS No.550-52-7), dissolve in 200mL of methanol and toluene (1:1 volume ratio) mixed solution, slowly drop (3eq ) 27.3mL trimethylsilyldiazomethane in n-hexane solution (concentration is 2mol / L), stirred at room temperature for 3h. TLC check, after the reaction is complete, add 0.5mL glacial acetic acid and stir for 10min to quench the reaction. The solvent was distilled off under reduced pressure and extracted with ethyl acetate and water (1:1, v / v). The ethyl acetate layer was concentrated under reduced pressure to obtain a crude product. The crude product was subjected to normal-phase silica gel column chromatography and gradient elution with petroleum ether-ethyl acetate (volume ratio: 50:1 to 1:1), and a total of 9.5 g of dark green chlorin e4 dimethyl ester was obtained. The yield was 90.3%. H...

Embodiment 2

[0129] Embodiment 2, Preparation of 3-hexyloxymethyl-3-desvinyl chlorin e4 disodium salt

[0130] Weigh 160 mg (0.25 mmol) of 3-hexyloxymethyl-3-desvinyl chlorin e4, dissolve it in 100 mL of acetone-methanol (20:1 by volume) mixed solution, and then slowly add A slight excess of 1mol / L sodium hydroxide-methanol solution, after the dark green solid is completely precipitated, it is filtered to obtain 3-hexyloxymethyl-3-desvinyl chlorin e4 disodium salt (CEFO), the purity (HPLC): 99.86%. The compound structure is as follows:

[0131]

Embodiment 3-4

[0132] Embodiment 3-4: adopt the same method as embodiment 2, wherein respectively use potassium hydroxide and ammonia water instead of sodium hydroxide to prepare corresponding potassium salt and ammonium salt, other reaction conditions are the same.

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Abstract

The invention provides a dihydroporphin compound as well as a preparation method and application thereof, and relates to the technical field of medicines. The dihydroporphin compound is a compound represented by a formula I, or a salt thereof, or a stereoisomer thereof, or a hydrate thereof, or a solvate thereof, or a prodrug thereof. The compound disclosed by the invention has a good effect when being used as a photosensitizer for photodynamic tumor treatment or a sound-sensitive agent for sonodynamic tumor treatment, and can be used for preparing medicines for treating tumors. Meanwhile, the compound disclosed by the invention is good in safety and small in toxic and side effects, and has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a chlorin compound and its preparation method and application. Background technique [0002] Cancer is one of the most stubborn diseases in the world today, and scientists have been looking for safe and reliable treatments for it. Photodynamic therapy (PDT) is a new technology for cancer treatment developed in the past 30 years. Since it entered clinical research in the 1970s, it has made breakthroughs in the treatment of tumors. It is limited to the treatment of malignant tumors, and it also shows good prospects in the treatment of many other diseases. [0003] PDT is the use of photodynamic effects of photosensitizers for disease treatment, currently mainly used for the treatment and diagnosis of malignant tumors and some precancerous lesions and benign lesions. Photodynamic therapy consists of two elements: a photosensitizer and a matching light source of a specific wavelen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K31/409A61P35/00A61P29/00A61P19/02A61P27/02A61P17/00
CPCC07D487/22A61P35/00A61P29/00A61P19/02A61P27/02A61P17/00Y02P20/55C07F1/005C07F1/04
Inventor 周先礼黄帅高峰陈琳
Owner SOUTHWEST JIAOTONG UNIV
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