CN114195840B - Method for identifying structure of macrolide compound - Google Patents

Method for identifying structure of macrolide compound Download PDF

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Publication number
CN114195840B
CN114195840B CN202111559130.5A CN202111559130A CN114195840B CN 114195840 B CN114195840 B CN 114195840B CN 202111559130 A CN202111559130 A CN 202111559130A CN 114195840 B CN114195840 B CN 114195840B
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ivermectin
ethyl
single crystal
furfural
ester derivative
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CN114195840A (en
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张辉
赵国富
徐海菊
冯尚坤
陈正冬
吴春艳
马子宾
韩露
鲍若晗
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Taizhou Vocational College of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
    • G01N23/20—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials
    • G01N23/20008—Constructional details of analysers, e.g. characterised by X-ray source, detector or optical system; Accessories therefor; Preparing specimens therefor
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
    • G01N23/20—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials
    • G01N23/207—Diffractometry using detectors, e.g. using a probe in a central position and one or more displaceable detectors in circumferential positions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Saccharide Compounds (AREA)

Abstract

The invention provides a method for preparing a macrolide compound into furfural ester, and then carrying out single crystal culture and crystal testing on the furfural ester to determine the crystal configuration of the macrolide compound. The method is reported for the first time, and single crystals of furfuryl ester derivatives after furyl ester formation are well cultivated, which is favorable for structural identification of macrolide compounds and has very important effect on development of the medicines.

Description

Method for identifying structure of macrolide compound
Technical Field
The invention relates to a preparation method of a macrolide compound furfural ester derivative and an application thereof in structural identification of the compound.
Background
According to the guidelines of chemical drug raw material preparation and structure validation research, all the monomers extracted from synthetic, semi-synthetic and natural materials and the main components in the drug components should be validated to confirm the chemical structure (including configuration). The basic principle is to provide sufficient experimental data and patterns, and to analyze correctly, so as to verify the structure of the drug molecule.
The content of the structure validation study mainly includes: planar structure, configuration, water of crystallization/crystallization solvent and crystalline form, and the like. The method for confirming the structure mainly adopts a spectrum analysis method, which comprises infrared, ultraviolet, nuclear magnetism and mass spectrum, and combines classical physicochemical analysis and element analysis. Other methods such as differential thermal analysis, thermogravimetric analysis, powder X-ray diffraction, etc. should be added as needed. The configuration of chiral medicine may be determined by single crystal X-ray diffraction, optical spectrum, circular dichroism and chemical method. Among them, single crystal X-ray diffraction is the most effective method in the structural identification of compounds. The premise of single crystal X-ray diffraction is that a suitable single crystal is grown, and thus, the growth of obtaining a single crystal of a related compound is very important.
Currently, single crystal X-ray diffraction can be performed by directly growing single crystals using the compound to be tested and determining the structure thereof is only a few. Macrolide compounds are very important, wherein the number of avermectin and milbemycins is tens of patent medicine compounds, and the 25-ethyl ivermectin which is an antibiotic heterozygous for the pharmaceutical and toxicological advantages is developing new pesticides and veterinary medicines. Many of these macrolides cannot grow single crystals, indirectly increasing the difficulty of drug development. For some macrolides which are difficult to directly culture single crystals, the derivatives are obtained by modification of the compounds, and then single crystal culture and X-ray diffraction are better methods for the derivatives.
The invention provides a method for preparing a macrolide compound into furfural ester, and then carrying out single crystal culture and crystal testing on the furfural ester to determine the crystal configuration of the macrolide compound. The method is reported for the first time, and after furfural ester is formed, single crystals are well cultivated, so that the method has very important effect on the development of the medicines.
Disclosure of Invention
The invention aims to provide a preparation method of a macrolide compound furfural ester derivative and an application thereof in structural identification of the compound.
The invention relates to a method which is characterized in that a macrolide compound is prepared into a furfural ester derivative, and then single crystal culture and crystal test are carried out on the derivative to determine the structure of the macrolide compound. Among them, macrolide compounds are required to have a hydroxyl group which reacts with furoyl chloride.
The macrolide compounds include avermectin compounds and milbemycin compounds. Some of these two classes of compounds are very difficult to crystallize, but have hydroxyl groups that react with furoyl chloride. The compound reacts with furfural chloride to obtain furfural ester derivative, and single crystals of the derivative are easier to culture.
The invention relates to structural identification of macrolides.
One embodiment relates to the structural determination of 25-ethylivermectin. The 25-ethyl ivermectin is reacted with furfural chloride to obtain 4', 5-biffuraldehyde and 25-ethyl ivermectin, the derivative is crystallized in methanol at low temperature to obtain crystals capable of carrying out single crystal diffraction, and the configuration of the crystals is finally determined.
Another embodiment relates to the structural determination of milbemycin A4. Milbemycin A4 is reacted with furfural chloride to obtain 5-furfural milbemycin A4, the derivative is crystallized in n-heptane at low temperature to obtain crystals capable of single crystal diffraction, and the configuration of the crystals is finally determined.
Due to the specificity of the chirality of the microbial product, one of the compounds is structurally defined and the remaining analogues are similarly configured to the defined compound.
Drawings
FIG. 1 is a diagram of the structure of a furfural ester of 25-ethylivermectin;
FIG. 2 is a diagram of the structure of the furfural ester of milbemycins A4.
Detailed Description
The following examples are further illustrative of the invention but are not intended to be limiting thereof. All other embodiments, based on the embodiments of the invention, which are apparent to those of ordinary skill in the art without undue burden are within the scope of the invention
Example 1
Determination of 25-ethyl ivermectin Single Crystal Structure
Into a dry and clean 250ml four-necked flask, methylene chloride and 8.72g (0.01 mol) of 25-ethylivermectin were charged and dissolved by stirring. Under the protection of nitrogen, 2.42g (0.024 mol) of triethylamine is added, the temperature is reduced to-5 ℃ to 0 ℃, a mixed solution of 2.74g (0.021 mol) of freshly distilled furoyl chloride and 10ml of dichloromethane is added dropwise, the dropwise is completed in about 30 minutes, and after 10 minutes, the TLC detection of the raw material point is basically disappeared.
The reaction was quenched by adding 50ml of saturated aqueous sodium bicarbonate, stirred for 15 minutes, allowed to stand for separation, the aqueous layer was back-extracted once with 50ml of dichloromethane, the organic layers were combined and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate to dryness gave 9.1g of the product, which was then subjected to column chromatography (Shimadzu LC-8A device, SIL-10AP autosampler,SPD-20A dectector and FRC-10A fraction collector;Shimadzu PRC-ODS,5 μm,25020mm i.d;20ml/min;210nm; shimadzu, japan) eluting with mobile phase methanol/water (80:20, volume ratio), and the desired fractions were collected and concentrated to dryness to give a colorless powder of 4', 5-biffuraldehyde, 25-ethylivermectin.
Dissolving the powder in methanol, cooling in a refrigerator for crystallization, obtaining a proper single crystal, then performing single crystal X-ray diffraction test to obtain the crystal structure of 4', 5-biffuraldehyde and 25-ethyl ivermectin, and determining the structure of the 25-ethyl ivermectin.
Example 2
Determination of the Single Crystal Structure of milbemycins A4
Into a dry and clean 250ml four-necked flask, methylene chloride and 8.0g of milbemycins A4 were charged and dissolved by stirring. Under the protection of nitrogen, 1.21g of triethylamine is added, the temperature is reduced to-5 ℃ to 0 ℃, a mixed solution of 1.4g of freshly distilled furoyl chloride and 5ml of dichloromethane is added dropwise, the dropwise is completed for about 30 minutes, and after 10 minutes, the TLC detects that the raw material point is basically disappeared.
The reaction was quenched by adding 30ml of saturated aqueous sodium bicarbonate, stirred for 15 minutes, allowed to stand for separation, the aqueous layer was back-extracted once with 50ml of dichloromethane, the organic layers were combined and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate to dryness gave 7.8g of the product, which was then subjected to column chromatography (Shimadzu LC-8A device, SIL-10AP autosampler,SPD-20A dectector and FRC-10A fraction collector;Shimadzu PRC-ODS,5 μm,25020mm i.d;20ml/min;210nm; shimadzu, japan) eluting with mobile phase methanol/water (90:10, volume ratio), and the desired fractions were collected and concentrated to dryness to give a colorless powder of 5-furfuramibemycin A4.
Dissolving the powder in n-heptane, cooling in a refrigerator for crystallization, obtaining a proper single crystal, then performing single crystal X-ray diffraction test to obtain the crystal structure of the 5-furfural milbemycin A4, and determining the structure of the milbemycin A4.

Claims (4)

1. The method for identifying the structure of the 25-ethyl ivermectin is characterized in that the 25-ethyl ivermectin is prepared into a furfural ester derivative, and then single crystal culture and crystal testing are carried out on the furfural ester derivative to determine the structure of the 25-ethyl ivermectin, wherein the structure of the furfural ester derivative of the 25-ethyl ivermectin is as follows:
2. the method according to claim 1, characterized in that the method for determining the structure of 25-ethylivermectin by preparing a furfural ester derivative of 25-ethylivermectin comprises the steps of:
(1) Firstly, using dichloromethane to dissolve 25-ethyl ivermectin, then adding triethylamine under the protection of nitrogen, cooling to-5-0 ℃, dropwise adding a newly steamed furoyl chloride solution, and completely reacting;
(2) After the reaction of the step (1) is completed, adding saturated sodium bicarbonate aqueous solution to quench the reaction, standing and layering, carrying out back extraction on a water layer by using dichloromethane once, combining organic layers, concentrating to dryness to obtain a product, then loading on a reverse phase preparation column for chromatographic elution, collecting the required fractions, concentrating to dryness to obtain colorless powder of 4', 5-biffurol and 25-ethyl ivermectin;
(3) The powder is dissolved in a solvent, placed in a refrigerator for cooling crystallization, and subjected to single crystal X-ray diffraction test after a proper single crystal is obtained.
3. The method of claim 2, wherein the reversed-phase preparative column chromatography conditions of step (2) are as follows: chromatographic column: shimadzu PRC-ODS,5 μm,250X 20mm; mobile phase: methanol/water 80:20 by volume.
4. The method of claim 2, wherein the solvent in step (3) is methanol.
CN202111559130.5A 2021-12-20 2021-12-20 Method for identifying structure of macrolide compound Active CN114195840B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998038201A1 (en) * 1997-02-27 1998-09-03 Antibioticos S.P.A. Process for the preparation of ivermectin
CN106148215A (en) * 2015-03-27 2016-11-23 浙江海正药业股份有限公司 A kind of streptomycete and the method producing mibemycin A4 thereof
CN110540556A (en) * 2018-05-28 2019-12-06 浙江海正药业股份有限公司 Method for separating and purifying ivermectin

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998038201A1 (en) * 1997-02-27 1998-09-03 Antibioticos S.P.A. Process for the preparation of ivermectin
CN106148215A (en) * 2015-03-27 2016-11-23 浙江海正药业股份有限公司 A kind of streptomycete and the method producing mibemycin A4 thereof
CN110540556A (en) * 2018-05-28 2019-12-06 浙江海正药业股份有限公司 Method for separating and purifying ivermectin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STRUCTURES OF MILBEMYCIN βl，β2，AND β3;Hiroshi Mishima et al;《Tetrahedron Letters》(第10期);第711-714页 *

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Assignor: TAIZHOU VOCATIONAL College OF SCIENCE & TECHNOLOGY

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Denomination of invention: A method for identifying the structure of macrolide compounds

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Assignee: ZHEJIANG HUIFENG PLASTICS Co.,Ltd.

Assignor: TAIZHOU VOCATIONAL College OF SCIENCE & TECHNOLOGY

Contract record no.: X2024980010522

Denomination of invention: A method for identifying the structure of macrolide compounds

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Assignee: Taizhou Chenda Sanitary Appliance Co.,Ltd.

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Denomination of invention: A method for identifying the structure of macrolide compounds

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Application publication date: 20220318

Assignee: Zhejiang Spray King Machinery Co.,Ltd.

Assignor: TAIZHOU VOCATIONAL College OF SCIENCE & TECHNOLOGY

Contract record no.: X2024330000652

Denomination of invention: A method for identifying the structure of macrolide compounds

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License type: Common License

Record date: 20240926