A kind of amino polyol fumagillin and its synthesis method and application

A technology of fumagillin and synthesis method, which is applied in the direction of medical preparations containing active ingredients, pharmaceutical formulas, drug combinations, etc., can solve problems such as poor water solubility, achieve reduced toxicity, non-toxic product solubility, and high product solubility Good results

Inactive Publication Date: 2018-12-18
BEE RES INST CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, it needs to be transformed into fumagillin cyclohexylamine salt (mainly dicyclohexylamine dicyclohexane) to improve water solubility and stability

Method used

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  • A kind of amino polyol fumagillin and its synthesis method and application
  • A kind of amino polyol fumagillin and its synthesis method and application
  • A kind of amino polyol fumagillin and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0028] The present embodiment provides amino polyol fumagillin as shown in formula I:

[0029]

[0030] Its NMR spectrum is shown in figure 1 .

Embodiment 2

[0032] This embodiment provides a method for synthesizing amino polyols, and the synthetic route is as follows:

[0033]

[0034] The specific operation steps are as follows:

[0035] 1.0g KBH 4 Dissolve it in 17ml of sodium hydroxide (0.05M) solution and gradually add it dropwise to a round bottom flask containing 1.0g of glucosamine hydrochloride. During the addition process, a large number of bubbles will appear (if the temperature rises sharply, vigorous stirring is required) , and slowly added). After reacting at room temperature for 2.5 h, the progress of the reaction was detected by TLC. If the reaction was complete, acetic acid was added to quench the reaction.

[0036] After the reaction solution was repeatedly washed with methanol, it was concentrated by distillation to obtain a white solid with a yield of more than 95% and a purity of 98%.

Embodiment 3

[0038] This embodiment also provides a method for synthesizing amine-based polyols. Compared with Example 2, the only difference is that individual operating parameters are different, specifically: adding NaBH 4 , LiAlH 4 or Pd / H 2 Reducing agent to replace KBH 4 .

[0039] The yield of the product obtained in this example is 80%-90%, and the purity is above 95%.

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Abstract

The invention relates to the field of compounds and in particular to amino-polyols substituted fumagillin as well as a synthetic method and application thereof. The amino-polyols substituted fumagillin has a structure as shown in a formula I. A novel derivative of the fumagillin provided by the invention (namely amino-polyols substituted fumagillin or fumagillin amino-polyols) has excellent water solubility and stability. When the preparation disclosed by the invention and common fumagillin bicyclohexane salts are used for treating ill swarm which is nearly consistent with Nosema apis under the equal concentration, the treatment effect of the amino-polyols substituted fumagillin disclosed by the invention is basically consistent with the effect of common fumagillin bicyclohexane salts. Because any bicyclohexane residue does not exist in the amino-polyols substituted fumagillin, the risk of bees and human health is reduced. Moreover, the product is high in solubility and stability. The structural formula is as shown in the specification.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to an amino polyalcohol-substituted fumagillin and its synthesis method and application. Background technique [0002] Fumagillin is a metabolite with various activities isolated from the fermentation broth of Aspergillus fumigatus. This substance has antibiotic activity and angiogenesis-inhibiting effect, thus having a therapeutic effect on tumor growth. In addition, a series of derivatives of fumagillin also have the effect of fighting against malaria parasites and sporozoites. Fumagillin is a very effective drug for the treatment of Nosema apis in beekeeping and has been used for nearly 60 years in countries such as the United States and Canada. It is currently the only drug that can effectively treat microsporidia in bees. However, due to its poor water solubility, it needs to be transformed into fumagillin cyclohexylamine salt (mainly dicyclohexylamine dicyclohexane) to impr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/22C07D301/00A61K31/336A61P33/02
CPCC07D301/00C07D303/22
Inventor 薛晓锋王彤彤吴黎明倪辉王敏王浩鹏赵柳微梁馨文
Owner BEE RES INST CHINESE ACAD OF AGRI SCI
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