Preparation method of protoporphyrin disodium

A technology of disodium porphyrin and porphyrin diester, applied in directions such as organic chemistry, can solve the problems of difficult separation of products, low final yield, and many reaction steps, and achieve the effects of easy operation, improved purity, and improved yield

Inactive Publication Date: 2018-11-06
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The total synthesis method generally has problems such as complex process, many reaction steps, low final yield, and difficult separation of products.

Method used

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  • Preparation method of protoporphyrin disodium
  • Preparation method of protoporphyrin disodium
  • Preparation method of protoporphyrin disodium

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[0029] The invention provides a kind of preparation method of disodium protoporphyrin, comprising the following steps:

[0030] (1) Protoporphyrin, anhydrous methanol and concentrated sulfuric acid undergo an alkyd reaction under ultrasonic conditions to obtain a protoporphyrin diester;

[0031] (2) Saponifying the protoporphyrin diester, NaOH methanol solution and toluene obtained in the step (1) under ultrasonic conditions to obtain disodium protoporphyrin.

[0032] In the invention, protoporphyrin, anhydrous methanol and concentrated sulfuric acid undergo alkyd reaction under ultrasonic conditions to obtain protoporphyrin diester. In the present invention, the ultrasonic frequency of the ultrasonic condition is preferably (0,80]KHz, more preferably [20,60]KHz. In the present invention, the power of the ultrasonic condition is preferably 0-400W, more preferably 100-400W.

[0033] In the present invention, the dosage ratio of the protoporphyrin, anhydrous methanol and conce...

Embodiment 1

[0064] Add hemin and acetic anhydride at a mass ratio of 1:45, measure acetic anhydride into an Erlenmeyer flask, then slowly add 1 mL of concentrated hydrochloric acid dropwise in a cold water bath, add 0.1 g of hemin and perform ultrasonic treatment, After reacting in a 40KHz, 250W ultrasonic reactor for 10 minutes, add 0.08 g of ferrous sulfate, and continue the ultrasonic reaction for 1 hour. After the reaction is over, add 4mol / L sodium hydroxide solution dropwise to adjust the pH of the solution to 5, take the precipitate after centrifugation, wash the precipitate twice with weakly acidic deionized water with a pH value of 4, and then continue to wash 3 times with deionized water . The crude product was purified by recrystallization with hot acetone and dried to obtain protoporphyrin.

[0065] Dissolve 0.1 g of protoporphyrin in 30 mL of anhydrous methanol, transfer them to a conical flask, add 0.7 mL of concentrated sulfuric acid, and sonicate at an ultrasonic frequenc...

Embodiment 2

[0069] Same as Example 1, the only difference is that the ultrasonic frequencies in the preparation process of protoporphyrin diester are 0, 20, 60, 80 KHz respectively.

[0070] The protoporphyrin diester that embodiment 1~2 makes carries out infrared spectrum research, and the result is as follows Figure 1~3 as shown, figure 1 Infrared wavelength 4000 ~ 400cm -1 Infrared spectrum, figure 2 Infrared wavelength 2000~1400cm -1 Infrared spectrum, image 3 Infrared wavelength 4000~2400cm -1 infrared spectrum. Depend on Figure 1~3 It can be seen that the protoporphyrin diesters prepared by the present invention are at 1697~1722cm -1 Weak peaks appear in the range, and the absorption peak in this band corresponds to the characteristic peak of C=O in the ester group. Affected by factors such as the synthesis method of the sample and its own purity, the same functional group will shift. 1600~1650cm -1 The existence of the characteristic peak of C=C at 1 shows that during...

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Abstract

The invention provides a preparation method of protoporphyrin disodium, and belongs to the field of synthesis of organic compounds. The method comprises the following steps: ensuring that protoporphyrin, absolute methanol and concentrated sulfuric acid are subjected to alcohol acid reaction in an ultrasound condition, so as to obtain protoporphyrin diester; ensuring that the protoporphyrin diester, a NaOH methanol solution and methylbenzene are subjected to saponification reaction in an ultrasound condition, so as to obtain the protoporphyrin disodium. The method has the advantages that assistance of ultrasonic wave is adopted to replace high-temperature reflux, so as to form the protoporphyrin disodium, hydrogen chloride gas is not required to be prepared during preparation, the adoptionof strong-toxicity reagents, such as chloroform, is further avoided, a high-temperature condition is not required to be use, the technology is simplified, and the whole process is easy to operate.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a preparation method of disodium protoporphyrin. Background technique [0002] Protoporphyrin disodium, as a member of the large family of porphyrin compounds, is composed of a porphyrin macrocycle composed of four pyrrole links, two groups of vinyl groups connected around the ring and two groups of sodium propionate, with a molecular weight of 607. Protoporphyrin disodium was first used in the clinical treatment of patients with liver dysfunction because of its hepatoprotective and hepatoprotective effects. At present, studies have also proved that disodium protoporphyrin has anti-hepatitis B and hepatitis C virus effects. In addition, disodium protoporphyrin also has the unique property of porphyrin compounds - photosensitization, porphyrin with abnormal affinity for some tumor cells will selectively gather around tumor cells, and then stimulated by specific...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
Inventor 靳国锋何立超马素敏金永国马美湖任景乐
Owner HUAZHONG AGRI UNIV
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