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Biosynthesis method and application of N-methyl-o-carborane-L-propionamide

A methyl-o-carborane, biosynthesis technology, applied in the directions of drug combinations, chemical instruments and methods, medical preparations containing active ingredients, etc., to achieve the effects of increasing cell affinity, solving technical bottlenecks, and increasing polarity

Active Publication Date: 2021-04-16
南京艾斯特医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But BPA has a disadvantage: once the BPA level in tumor cells rises, it will be excreted through the "anti-transport" mechanism, which makes BNCT somewhat limited

Method used

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  • Biosynthesis method and application of N-methyl-o-carborane-L-propionamide
  • Biosynthesis method and application of N-methyl-o-carborane-L-propionamide
  • Biosynthesis method and application of N-methyl-o-carborane-L-propionamide

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Embodiment 1～3

[0021] Embodiment 1~3 is the preparation embodiment of L-propionamide hydrochloride

Embodiment 1

[0023] Add 10 grams of D,L-alanine and 50 grams of 25% ammonia water into a 250 ml single-necked flask, add 60 grams of water for dilution, and then stir while the temperature of the system rises to 35-37 ° C, add 0.1 grams of laccase, React for 16-18 hours. After the reaction is complete, filter out the laccase and keep it frozen for future use. The filtrate was directly passed through hydrogen chloride until the pH value of the system reached 4.3-4.5 to precipitate a solid, which was filtered and dried to obtain 8.4 g of L-propionamide hydrochloride. The yield is 84% ​​based on the mass of D,L-alanine.

Embodiment 2

[0025] Add 10 grams of D,L-alanine and 50 grams of 25% ammonia water into a 250 ml single-necked flask, add 60 grams of water for dilution, and then stir while the temperature of the system rises to 38-40 °C, add 0.1 grams of laccase, React for 16-18 hours. After the reaction is complete, filter out the laccase and keep it frozen for future use. The filtrate was directly passed through hydrogen chloride until the pH value of the system reached 4.3-4.5 to precipitate a solid, which was filtered and dried to obtain 9.2 g of L-propionamide hydrochloride. The yield is 92% based on the mass of D,L-alanine.

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Abstract

The invention discloses a biosynthesis method of N-methyl-o-carborane-L-propionamide, which comprises the following steps: 1, synthesizing L-propionamide by using D,L-alanine and ammonia water as raw materials and laccase as a catalyst, filtering the reaction product to remove the laccase, and introducing hydrogen chloride gas to generate L-propionamide hydrochloride; 2, in an organic solvent or ionic liquid, reacting with 1-bromomethyl-o-carborane under an alkaline condition to obtain the corresponding o-carborane derivative. According to the invention, through the degradation characteristics of laccase on amines and alcohols, it is accidentally found that laccase has the function of synthesizing the L-propylamine amide, and has the characteristics of high yield, safety, no pollution and the like. Therefore, by chemically synthesizing and modifying o-carborane and a relatively hydrophilic group L-propionamide, the purpose of increasing the polarity and cell affinity of the compound is achieved, so that the technical effect of targeted enrichment and high concentration of boron ions in tumor cells is achieved.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, in particular to a biosynthetic method of N-methyl-o-carborane-L-propionamide and its application. Background technique [0002] L-propionamide hydrochloride is a white crystal, which is easily soluble in water, soluble in ethanol, and insoluble in ether or n-butanol. The chemical formula of L-alaninamide hydrochloride is: C3H8N2O·HCl, molecular weight: 124.57. It is a widely used amino acid derivative, mainly used in the field of medicine. With the development of some downstream products, L-alaninamide hydrochloride The demand for salt is getting wider and wider, but the preparation of L-propionamide hydrochloride is through chemical synthesis. The industrial production of isopropylamine mainly has the following methods: [0003] Dissolve L-alanine in methanol, add an appropriate amount of chloride catalyst to carry out esterification reaction, the chloride is thionyl chlori...

Claims

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Application Information

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IPC IPC(8): C07F5/05C12P13/02A61K41/00A61P35/00
CPCY02P20/54
Inventor 张红夺金峰金涛王雯金成福李仙洛
Owner 南京艾斯特医药科技有限公司
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