CN109053747A - A kind of compound and its preparation method and application - Google Patents
A kind of compound and its preparation method and application Download PDFInfo
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- CN109053747A CN109053747A CN201811009730.2A CN201811009730A CN109053747A CN 109053747 A CN109053747 A CN 109053747A CN 201811009730 A CN201811009730 A CN 201811009730A CN 109053747 A CN109053747 A CN 109053747A
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
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Abstract
The present invention provides a kind of compound and its preparation method and application, shown in the structural formula of compound such as formula (I), the preparation method includes the following steps: that white-rot fungi is carried out Liquid Culture by (1)；(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C stand 20 days or more；(3) fluid nutrient medium after standing is separated with white-rot fungi, ethyl acetate extraction is added into the liquid after separation, obtains supernatant；(4) concentrated supernatant, and gradient elution is carried out with silica gel chromatography, thin-layered chromatography carries out the tracking of metabolite；(5) the isolated product of silica gel chromatograph is further isolated and purified by preparative liquid chromatography, obtains the compound of high-purity.The Compound nomenclature are as follows: N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide, it is able to suppress the survival of marrow neuroblastoma cell, the preparation method utilizes microorganism, white-rot fungi breeding is fast, it can be widely applied, production cost is low, and can be used for dinotefuran of degrading simultaneously.
Description
Technical field
The present invention relates to compound fields, and in particular to a kind of compound and its preparation method and application.
Background technique
White-rot fungi plays a significant role in the nature ecosystem, is a kind of living resources of preciousness, is that environment is controlled
The tool and research mode object of reason.White-rot fungi is not required to the fore condition by specific pollutants before Recalcitrant chemicals of degrading
Change, the different pollutant of a large amount of structures that can degrade, and low to nutritional condition requirement, cost can be saved.White-rot fungi
Phanerochaete sordida YK-624 (hereinafter referred to as YK-624) is to numerous Recalcitrant chemicals such as aflatoxin
Ability has higher than type strain Phanerochaete chrysosporium.White-rot fungi processing organic pollutant in show it is wide before
Scape makes full use of white-rot fungi to the realistic meaning of environment remediation.
Summary of the invention
The purpose of the present invention is to provide a kind of compounds and its preparation method and application.
To achieve the above object, the technical solution of the present invention is as follows: a kind of compound, the structural formula of the compound such as formula
(I) shown in:
Molecular formula C7H12N4O3, molecular weight 200, name are as follows: N-
((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide, English name are as follows: N- ((4aS,
7aS,E)-1-methylhexahydrofuro[2,3-d]pyrimidin-2(1H)-ylidene)nitramide(PHPF)。
The present invention also provides a kind of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunits)
The preparation method of nitramide, the described method comprises the following steps:
(1) white-rot fungi (YK-624) is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C stand 20 days with
On；
(3) fluid nutrient medium after standing is separated with white-rot fungi, octanol/water distribution is added into the liquid after separation
Organic solvent of the logarithm range of coefficient in 0.70-0.80 extracts, and obtains supernatant；
(4) concentrated supernatant, and carry out gradient elution with silica gel chromatography, thin-layered chromatography carry out metabolite with
Track；
(5) the isolated product of silica gel chromatograph is further isolated and purified by preparative liquid chromatography, obtains high-purity
N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight: 9-11 parts of glucose, 0.2-0.3 portions of wine
Stone acid ammonium, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 parts of Kirk salting liquids.
Wherein, the Kirk salting liquid includes following components in percentage by weight: 1.8-2.2% potassium dihydrogen phosphate, 0.4-
0.6% bitter salt, 0.11-0.15% CALCIUM CHLORIDE DIHYDRATE, 0.0009-0.0011% thiamine hydrochloride, 1.5-1.8%
Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient: three enzyme acid esters of 0.8-1% nitrilo-
(Nitrilotriacetate), 0.30.2-0.4% bitter salt, 0.3-0.5% manganese sulfate monohydrate, 0.5-0.7% chlorine
Change sodium, 0.04-0.07% green vitriol, 0.09-0.12% Cobalt monosulfate heptahydrate, seven hydrated sulfuric acid of 0.09-0.12%
Zinc, 0.05-0.07% CALCIUM CHLORIDE DIHYDRATE, 0.005-0.007% Salzburg vitriol, 0.009-0.012% 12 are hydrated sulphur
Sour aluminium potassium, 0.005-0.007% boric acid, bis- molybdic acid hydrate sodium of 0.006-0.008%.
Preferably, the fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight: 10 parts of glucose, and 0.221
Part ammonium tartrate, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
Preferably, the Kirk salting liquid includes following components in percentage by weight: 2% potassium dihydrogen phosphate, 0.5% 7 water
Close magnesium sulfate, 0.13% CALCIUM CHLORIDE DIHYDRATE, 0.001% thiamine hydrochloride, 1.67%Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient: 0.9%Nitrilotriacetate, and 0.3% 7
Magnesium sulfate heptahydrate, 0.42% manganese sulfate monohydrate, 0.6% sodium chloride, 0.06% green vitriol, 0.11% 7 hydrated sulfuric acid
Cobalt, 0.11% Zinc vitriol, 0.06% CALCIUM CHLORIDE DIHYDRATE, 0.006% Salzburg vitriol, 0.011% 12 hydration
Aluminum aluminum sulfate, 0.006% boric acid, 0.007% 2 molybdic acid hydrate sodium.
Preferably, the white-rot fungi (YK-624), which carries out liquid cultivating method, is: taking in potato agar glucose culture
The white-rot fungi mycelia piece activated on base (PDA) is seeded in the fluid nutrient medium, 24~30 DEG C of progress Liquid Cultures.
Preferably, the method for the activation are as follows: activated on potato glucose agar medium (PDA), potato glucose
Agar medium includes following components: potato 20%, glucose 2%, agar 2%.
Preferably, dwell temperature described in step (2) is 30 DEG C.
Preferably, the time cultivated in step (1) is 3~5 days.
Preferably, the temperature of Liquid Culture is 24-30 DEG C in step (1).
Preferably, the concentration of the dinotefuran in liquid medium is 0.05-0.15mmol/L.
Preferably, the concentration of the dinotefuran in liquid medium is 0.1mmol/L.
Preferably, the organic solvent is ethyl acetate.
Preferably, the method for the extraction is comprising steps of with the ethyl acetate of the liquid volume after the 0.5-2 times of separation
Extract 2-3 obtained supernatant.
Preferably, the model of the chromatographic column of the preparation chromatography are as follows: Inertsil C30S-Select 5m 20x
250mm。
Preferably, the mode that fluid nutrient medium is separated with white-rot fungi in step (3) is selected from centrifugation or filtering.
Preferably, the method for the concentrated supernatant is selected from rotary evaporation or freeze-drying.
The present invention also provides a kind of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunits)
Nitramide is preparing the purposes for inhibiting the drug of people's bone spinal nerve blastoma cell survival.
The present invention also provides a kind of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunits)
Nitramide is in preparation for preventing and treating abdominal tumor, breast tumor, tumour, paraneoplastic syndrome or metastatic tumo(u)r by vertebra
The purposes of the drug of disease.
The beneficial effects of the present invention are: the present invention provides a kind of compound and preparation method, the preparation methods of invention
Dinotefuran is acted on using white-rot fungi (YK-624), qualitative analysis has been carried out to the product of effect, is prepared for a kind of new
Compound, N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide is prepared
Compound be able to suppress marrow neuroblastoma cell survival, the preparation method utilize microorganism, white-rot fungi breeding
Fastly, it can be widely applied, production cost is low, and can be used for dinotefuran of degrading simultaneously.
Detailed description of the invention
Fig. 1 is the structure of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide
Formula figure.
Fig. 2 is the mass spectrum of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide
Figure.
Fig. 3 is N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide1H-
NMR(CD3OD) figure.
Fig. 4 is N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide13C-
NMR(CD3OD) figure.
Fig. 5 is that N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide inhibits people
The effect picture of marrow neuroblastoma cell line SH-SY5Y.
Specific embodiment
The present invention is specifically described below with reference to embodiment, but not limited to this.
Embodiment 1
1. experimental material
White-rot fungi YK-624 potato glucose agar medium (PDA, ingredient: potato 20%, glucose 2%, agar
2%) it carries out passage and expands culture, saved backup in 4 DEG C of refrigerators.
2. a kind of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitre of the invention
The preparation method of amide, the described method comprises the following steps:
(1) take at 30 DEG C of piece of white-rot fungi (YK-624) mycelia of the two panels diameter 10mm activated in PDA culture medium into
Row Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 30 DEG C stand 20 days or more；
(3) fluid nutrient medium after standing is separated with white-rot fungi, isometric acetic acid second is added into the liquid after separation
Ester extracts 3 times, merges supernatant；
(4) evaporation and concentration supernatant is chosen to install, and carries out gradient elution with silica gel chromatography, thin-layered chromatography carries out metabolism production
The tracking of object；
(5) the isolated product of silica gel chromatograph is further isolated and purified by preparative liquid chromatography.
The model of the chromatographic column of the preparation chromatography are as follows: Inertsil C30S-Select 5m 20x 250mm.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight: 10 parts of glucose, 0.221 part of tartaric acid
Ammonium, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
The Kirk salting liquid includes following components in percentage by weight: 2% potassium dihydrogen phosphate, 0.5% 7 hydrated sulfuric acid
Magnesium, 0.13% CALCIUM CHLORIDE DIHYDRATE, 0.001% thiamine hydrochloride, 1.67%Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient: 0.9%Nitrilotriacetate, and 0.3% 7
Magnesium sulfate heptahydrate, 0.42% manganese sulfate monohydrate, 0.6% sodium chloride, 0.06% green vitriol, 0.11% 7 hydrated sulfuric acid
Cobalt, 0.11% Zinc vitriol, 0.06% CALCIUM CHLORIDE DIHYDRATE, 0.006% Salzburg vitriol, 0.011% 12 hydration
Aluminum aluminum sulfate, 0.006% boric acid, 0.007% 2 molybdic acid hydrate sodium.
3. the qualitative analysis of purified compound
(1) it is analyzed by ESI-TOF-MS, mass spectrogram [M-H]-As shown in Fig. 2, [M-H]-=199.02 know compound
Molecular weight is 200.
(2) by spectral analysis of the nuclear magnetic resonance, in CD3Hydrogen spectrogram in OD as shown in figure 3, its in CD3Carbon spectrum in OD
Figure is as shown in Figure 4.Analysis to hydrogen spectrogram dynamic respond and the analysis to carbon spectrogram dynamic respond, the results are shown in Table 1.
Table 1
By to compound1H-NMR(CD3OD) spectrogram and13C-NMR(CD3OD) the analysis of spectrogram and mass spectrogram, confirmation system
The structural formula of standby obtained compound is as follows:
Molecular formula C7H12N4O3, molecular weight 200, name are as follows: N- ((4aS,
7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide, English name are as follows: N- ((4aS, 7aS, E) -
1-methylhexahydrofuro[2,3-d]pyrimidin-2(1H)-ylidene)nitramide(PHPF)。
Embodiment 3
It is prepared by a kind of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide
For inhibiting the embodiment of the purposes of the drug of people's bone spinal nerve blastoma cell survival.
N- ((4aS, 7aS, the E) -1- methyl six of 0.3mM is added into people's bone spinal nerve blastoma cell strain SH-SY5Y
Hydrogen furans [2,3-d] pyrimidine -2 (1H)-subunit) nitramide, control group addition do not contain nitramide DMSO solvent, discovery with it is right
It is compared according to group, has 69.3% cell survival relatively, illustrate N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -
2 (1H)-subunits) nitramide is able to suppress people's bone spinal nerve blastoma cell survival.
Therefore, N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide can be used
In preparing the drug for inhibiting people's bone spinal nerve blastoma cell survival, N- ((4aS, 7aS, E) -1- methyl hexahydro furyl
[2,3-d] pyrimidine -2 (1H)-subunit) nitramide can be used in preparation treat and prevent people's bone spinal nerve blastoma cell cause
Disease drug, disease caused by people's bone spinal nerve blastoma cell include abdominal tumor, breast tumor, tumour by vertebra,
Paraneoplastic syndrome or metastatic neoplastic diseases.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than protects to the present invention
The limitation of range is protected, although the invention is described in detail with reference to the preferred embodiments, those skilled in the art should
Understand, it can be with modification or equivalent replacement of the technical solution of the present invention are made, without departing from the essence of technical solution of the present invention
And range.
Claims (8)
1. a kind of compound, which is characterized in that shown in the structural formula of the compound such as formula (I):
2. a kind of preparation method of compound as described in claim 1, the described method comprises the following steps:
(1) white-rot fungi is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C stand 20 days or more；
(3) fluid nutrient medium after standing is separated with white-rot fungi, Octanol/water Partition Coefficients is added into the liquid after separation
Logarithm range 0.70-0.80 organic solvent extract, obtain supernatant；
(4) concentrated supernatant, and gradient elution is carried out with silica gel chromatography, thin-layered chromatography carries out the tracking of metabolite；
(5) the isolated product of silica gel chromatograph is further isolated and purified by preparative liquid chromatography, obtains the described of high-purity
Compound.
3. according to the method described in claim 2, it is characterized in that, the organic solvent is ethyl acetate.
4. according to the method described in claim 2, it is characterized in that, the method for the extraction is the following steps are included: with 0.5-2 times
The ethyl acetate of liquid volume after the separation extracts 2-3 obtained supernatant.
5. method according to claim 2, which is characterized in that the fluid nutrient medium of the Liquid Culture includes following parts by weight
Component: 9-11 parts of glucose, 0.2-0.3 parts of ammonium tartrates, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 parts of Kirk salting liquids.
6. according to the method described in claim 2, it is characterized in that, the fluid nutrient medium of the Liquid Culture includes following weight
The component of part: 10 parts of glucose, 0.221 part of ammonium tartrate, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
7. a kind of drug of compound as claimed in claim 1 in preparation for inhibiting people's bone spinal nerve blastoma cell survival
Purposes.
8. a kind of compound as claimed in claim 1 preparation for preventing and treating abdominal tumor, breast tumor, tumour by vertebra,
The purposes of the drug of paraneoplastic syndrome or metastatic neoplastic diseases.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114540431A (en) * | 2022-02-18 | 2022-05-27 | 广州大学 | Method for biologically preparing 4, 4' -dihydroxy benzophenone by white rot fungi |
| CN114634954A (en) * | 2022-02-18 | 2022-06-17 | 广州大学 | Method for biodegradation and conversion of organic pollutants |
| CN114699705A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
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| CN114634954A (en) * | 2022-02-18 | 2022-06-17 | 广州大学 | Method for biodegradation and conversion of organic pollutants |
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| CN114699705A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
| CN114699705B (en) * | 2022-05-06 | 2022-12-16 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
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| Publication number | Publication date |
|---|---|
| CN109053747B (en) | 2020-04-28 |
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