CN112920194B - Chromene coumarin derivative containing fluorine functional group and preparation method and application thereof - Google Patents
Chromene coumarin derivative containing fluorine functional group and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a coumarin derivative containing fluorine functional groups of chromenes and a preparation method and application thereof, which are characterized in that the structure of the coumarin derivative is shown as a formula I, the preparation method comprises the specific steps of putting 2 mmol of 4-hydroxycoumarin, 3 mmol of p-fluorobenzaldehyde, 2 mmol of malononitrile and 0.1 mmol of sodium dodecyl sarcosine into a round-bottom flask, adding 10 mL of water as a solvent, stirring for 5 hours at the temperature of 60-65 ℃, filtering and removing water after the reaction is finished to obtain a crude product, and recrystallizing the crude product by adopting dichloromethane to obtain 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene Easy to transform.
Description
Technical Field
The invention relates to coumarin derivatives, in particular to a chromene coumarin derivative containing fluorine functional groups, and a preparation method and application thereof.
Background
The coumarin belongs to heterocyclic compounds of phthalimidine, has various biological activities such as antibiosis, anti-inflammation, antioxidation, antitumor, antivirus and the like, is easy to synthesize and convert into various functionalized coumarins, and is widely applied to the fields of medicines and pesticides. White spot syndrome is classified as one of the animal diseases that must be reported by the world animal health Organization (OIE). Since white spot syndrome virus was isolated and identified, researchers have been working on finding therapeutic means that can effectively control this virus. Generally, research and application of fishery vaccines and basic innovation research and industrialization of pollution-free aquatic fishery drugs with high efficiency, low toxicity, low residue and small environmental pollution are effective means for controlling disease occurrence and guaranteeing safety and ecological safety of aquatic products at present. However, since the immune system of the larval animal has not yet fully developed, variation of pathogens and diversity of antigens are also among the most important factors affecting the use of vaccines for fishing. Therefore, the research of the drug prevention and treatment technology has important significance for the prevention and control of white spot syndrome and other aquatic virus diseases and the healthy culture.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a chromene fluorine-containing functional group coumarin derivative which has an excellent effect of resisting white spot syndrome virus, relatively simple synthesis process, high yield and easy conversion, and a preparation method and application thereof.
The technical scheme adopted by the invention for solving the technical problems is as follows: a structure of a coumarin derivative containing a chromene fluorine-containing functional group is shown as a formula I:
formula I.
The preparation method of the coumarin derivative with the chromene fluorine-containing functional group comprises the following steps: biginelli reaction is carried out on 4-hydroxycoumarin, p-fluorobenzaldehyde and malononitrile to prepare 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene.
The method comprises the following specific steps: placing 2 mmol 4-hydroxycoumarin, 3 mmol p-fluorobenzaldehyde, 2 mmol malononitrile and 0.1 mmol sodium dodecyl sarcosinate in a round bottom flask, adding 10 mL water as a solvent, stirring for 5H at 60-65 ℃, after the reaction is finished, filtering and removing water to obtain a crude product, and recrystallizing the crude product by dichloromethane to obtain 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, wherein the structure of the chromene is shown as a formula I:
formula I.
The coumarin derivative containing the fluorine functional groups of the chromene is applied to the preparation of the medicine for inhibiting the white spot syndrome virus.
Compared with the prior art, the invention has the advantages that: the coumarin derivative has good killing activity on the white spot syndrome virus, has an excellent antiviral effect, is relatively simple in synthesis process, high in yield and easy to convert, and has an application value in preventing and treating aquatic virus diseases.
Drawings
FIG. 1 is a schematic diagram of the general synthetic route for 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene;
FIG. 2 is a graph of copy number of WSSV and mortality of shrimp larvae, wherein A is an inhibition graph of copy number of WSSV by 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene at different concentrations, B is a survival graph of shrimp larvae for 72H under 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene at different concentrations, C is a graph of survival rate of shrimp larvae for 72H under 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene and WSSV simultaneously soaking shrimp larvae 24, copy number plots of WSSV after 48 and 72 h;
FIG. 3 is a copy number graph of WSSV and a mortality graph of shrimp larvae, wherein A is a copy number graph of WSSV after preincubation of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene 1, 2, and 4H followed by infection of shrimp larvae, and B is a mortality graph of WSSV after preincubation of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene 1, 2, and 4H followed by infection of shrimp larvae and shrimp larvae;
FIG. 4 is a copy number diagram of WSSV and a mortality diagram of shrimp larvae, wherein A is a copy number diagram of WSSV reinfected after shrimp preincubation of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene 1, 4 and 8H, and B is a copy number diagram of WSSV reinfestated after shrimp preincubation of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene 1, 4 and 8H, and a mortality diagram of shrimp larvae;
FIG. 5 is a copy number graph of WSSV and a death curve of shrimp larvae, wherein A is a mortality graph of shrimp larvae infected with WSSV without replacing 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, B is a mortality graph of shrimp larvae infected with WSSV with one replacement of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, C is a mortality graph of shrimp larvae infected with WSSV with two replacements of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, and D is a mortality graph of shrimp larvae infected with WSSV with three replacements of 4-fluorophenyl-3-cyano-2-amino-5-des, and D is a mortality graph of shrimp larvae infected with three replacements of 4-fluorophenyl-3-cyano-2-amino-5-des oxy-4H, 5H-pyrone [3,2-c ] chromene, mortality map of WSSV shrimp larvae infected with E is a four-time change of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, mortality map of WSSV shrimp larvae infected with E is a five-time change of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, mortality map of WSSV shrimp larvae infected with G is a five-time change of 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, copy number plots of WSSV;
FIG. 6 is a copy number diagram of WSSV and a mortality diagram of shrimp larvae, wherein A is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, which is left standing in a culture water body for 0H, and then shrimp larvae are soaked together with WSSV, B is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, which is left standing in a culture water body for 0H, and shrimp larvae are soaked together with WSSV, and mortality diagram of shrimp larvae, C is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-C ] chromene, which is left standing in a culture water body for 24H, and then shrimp larvae are soaked together with WSSV, a copy number diagram of WSSV, D is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene in a culture water body after standing for 24H and simultaneously soaking shrimps with WSSV, a mortality diagram of shrimps, E is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene in the culture water body after standing for 48H and simultaneously soaking shrimps with WSSV, a copy number diagram of WSSV, F is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene in the culture water body after standing for 48H and simultaneously soaking shrimps with WSSV, the death rate chart of the young shrimps is shown in the specification, G is a copy number chart of the WSSV, the young shrimps are soaked by 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene after standing for 72H in the aquaculture water body and the WSSV at the same time, H is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene after standing for 72H in the aquaculture water body and the WSSV at the same time, the death rate chart of the young shrimps is shown in the specification, I is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene after standing for 96H in the aquaculture water body and the WSSV at the same time, and J is 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, and the mortality rate of the shrimps is shown by standing for 96H in a culture water body and soaking the shrimps with the WSSV.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
Detailed description of the preferred embodiment
A structure of a coumarin derivative containing a chromene fluorine-containing functional group is shown as a formula I:
formula I.
Detailed description of the invention
1. In the first embodiment, the preparation method of the coumarin derivative is as shown in fig. 1, and the steps are as follows
formula I.
2. The structural data of the target compounds are shown in tables 1 and 2:
TABLE 1 Properties of the Compounds
TABLE 2 preparation of the compounds1H NMR、13C NMR and ESI-MS data
As can be seen from Table 1, the preparation method of the target compound provided by the invention has high yield, and the structure of the target compound, the specific chemical shifts of the target compound, such as 4.50 of the hydrogen spectrum and 36.26 of the carbon spectrum in Table 2, can be determined from Table 2, which proves the correctness of the structure of the reaction product.
Detailed description of the preferred embodiment
1. Determination of anti-white spot syndrome virus activity
(1) Test materials
Virus material: white Spot Syndrome Virus (WSSV) from the institute of mariculture in Zhejiang province; experimental animals: penaeus vannamei (Pacific white shrimp post-larvae) comes from Qingjiang base of research institute of mariculture in Zhejiang province.
Preparing a liquid medicine to be detected: accurately weighing 500 mg of coumarin derivatives (compounds represented by formula I or C5 for short) with structures shown in formula I, respectively placing in 10 mL volumetric flasks, adding dimethyl sulfoxide (DMSO) for dissolution and fixing volume to obtain liquid medicine to be measured with concentration of 50 mg/mL, and storing in a refrigerator at 4 ℃ for later use.
(2) WSSV challenge concentration detection method
Litopenaeus vannamei was randomly added to six-well plates containing 6 mL of aquaculture water and 10 litopenaeus vannamei per well. The WSSV groups were soaked in virus dilutions of 1.6 × 10 concentration4、1.6×105、1.6×106、1.6×107And 1.6X 108copies/. mu.L. The blank control group only had aquaculture water. The temperature was maintained at 28. + -. 0.5 ℃ during the test. The test lasted 3 d and shrimp deaths were recorded every 24 h. According to the test results, the WSSV concentration at which the death rate of the young shrimps within 3 d reaches 100% is selected as the challenge concentration of the subsequent test.
(3) Toxicity test of compound of formula I on Penaeus vannamei Boone
Litopenaeus vannamei was randomly added to six-well plates containing 6 mL of aquaculture water and 10 litopenaeus vannamei per well. The young shrimps are respectively soaked in liquid medicine (0.1-40 mg/L) to be detected with different concentrations, and a solvent control group (soaked in 0.08% DMSO) and a blank control group are arranged. The temperature was maintained at 28. + -. 0.5 ℃ and shrimp survival was observed and recorded for 72 hours.
(4) Test for antiviral Activity of Compounds of formula I
A. Litopenaeus vannamei was randomly added to six-well plates containing 6 mL of aquaculture water and 10 litopenaeus vannamei per well. Soaking young shrimp in WSSV diluent (final concentration of 1.6 × 10)6copies/. mu.L) and test solutions (0.32, 0.63, 1.25, 25, 5 and 10 mg/L). Control groups were added WSSV virus dilutions and 0.02% DMSO. Observing survival condition of the shrimps every 12 h;
c5 (10 mg/L) and WSSV dilutions (8X 10)7copies/. mu.L) pre-incubation for 1, 2 or 4h, control incubation with 0.04% DMSO, followed by 50-fold dilution of the mixture to soak shrimp, at which point the concentration of C5 is 0.4 mg/L (C5 is not functional), and the concentration of copies of WSSV dilutions is 1.6X 106copies/. mu.L, incubated at 28 ℃ for 144 h, and shrimp survival was recorded every 12 h. In addition, the shrimp was treated as above, and the shrimp was collected at 72 hours;
C. soaking young shrimp 10 mg/L C5, 2%Incubating at 8 deg.C for 1, 4 or 8 hr, adding 0.04% DMSO into control group, removing solution, washing culture water for 3 times, and adding WSSV diluent (final concentration of 1.6 × 10)6copies/. mu.L), incubated at 28 ℃ for 144 h, and shrimp survival was recorded every 12 h. In addition, the shrimp was treated as above, and the shrimp was collected at 72 hours;
D. randomly adding Penaeus vannamei Boone into six-well plate containing 6 mL of aquaculture water and 10-tailed shrimps per well, setting a, b, c, d, e and f six experimental groups, adding WSSV diluent (final concentration of 1.6 × 10)6copies/mu L), removing the solution after 24 h, washing the aquaculture water body for 3 times, adding 10 mg/L C5 or 0.02% DMSO, replacing fresh C5 or DMSO every 24 h, and replacing the aquaculture water body in a control group. Group a was changed 0 times, group b was changed 1 time, group c was changed 2 times, group d was changed 3 times, group e was changed 4 times, group f was changed 5 times, cultured at 28 ℃ for 144 hours, and the mortality of shrimp was recorded every 12 hours. The experimental method is the same as above, five times of medicines are continuously replaced, the culture is carried out for 144 h at the temperature of 28 ℃, and three young shrimps are taken every 8 h. Extracting DNA with a marine animal tissue genome DNA rapid extraction kit (Tiangen), and storing at-80 ℃ for later use.
(5) Water stability of Compounds of formula I
Dissolving the compound of formula I in aquaculture water, standing at 28 deg.C for 0, 1, 2, 3 and 4 days, mixing the water sample containing the compound of formula I with virus solution, and soaking prawn in the mixture, wherein the concentrations of the compound of formula I and WSSV diluent are 10 mg/L and 1.6 × 106culturing copies/mu L at 28 deg.C for 72 hr, collecting young shrimp, extracting DNA, and storing at-80 deg.C.
(6) Detection of WSSV genomic DNA copy number
After completion of the DNA extraction, the concentration and purity thereof were measured using a ultramicrospectrophotometer. The DNA was diluted with sterile water to a concentration of 30 ng/. mu.L as a template for RT-qPCR. The detection primer is VP28141(VP 28-F: 5'-AAACCTCCGCATTCCTGTGA-3', VP28-R: 5'-TCCGCATCTTCTTCCTTCAT-3'), RT-qPCR reaction system and reaction procedure are shown in tables 3 and 4. Quantitative PCR results were based on pMD19T-VP28141And converting a standard curve made by the standard substance to obtain the virus copy number.
TABLE 3 PCR reaction System
TABLE 4 PCR reaction procedure
The compound of formula I has crystal precipitation at 20-40 mg/L and has no effect on the survival rate of young shrimps at 10 mg/L. 1.6X 106When the shrimp is soaked in the WSSV diluent of copies/mu L, the death rate of the shrimp within 3 d is 100%, so the virus concentration is selected as the challenge concentration of the subsequent experiment.
The inhibitory effect of compounds of formula i on WSSV replication in shrimp bodies is shown in figure 2A. C5 can obviously inhibit the replication of WSSV at 1.25 mg/L, and the inhibition rate of virus replication at 10 mg/L exceeds 90%. The protection rate of C5 against WSSV shrimp infection increased in a concentration-dependent manner, and the protection rate of shrimp at 10 mg/L was over 50% within 72 h (FIG. 2B). In addition, C5 significantly inhibited WSSV proliferation in shrimp larvae at 24, 48, and 72 h. WSSV copy number decreased 2.3, 2.4 and 2.7 fold after C5 preincubation of WSSV virions 1, 2 and 4h, respectively (fig. 3A), compared to WSSV control groupDMSO-4 hCumulative mortality of shrimp in the group was 100% over 84 h, whereas in WSSVC5-4 hThe cumulative mortality rate in 84 h of shrimp in the group was 40%, and shrimp survived at 144 h (fig. 3B) it can be seen that C5 was effective in reducing the infectivity of the virions, and this weakening was more pronounced with prolonged drug preincubation virus time. Furthermore, C5 was not effective in preventing WSSV infection in shrimp after pre-incubation (FIGS. 4A-B).
The effect of successive dressing changes on the antiviral efficacy of C5 is shown in figure 5. After the shrimp is infected with WSSV for 24 hours, the WSSV is used without changing the culture water body and the medicinesDMSOThe shrimp in the treatment group died starting at 12 h, with a cumulative mortality rate of 100% at 60 h, while the shrimp in the C5-WSSV group treated without changing the drug did begin at 36 hDeath began to occur at h and the cumulative mortality reached 100% at 108 h. Subsequently, the cumulative mortality rate of the shrimp infected with WSSV in the C5-WSSV treatment group at 108 h decreased from 100% to 25% by changing the drug 1, 2, 3, 4 and 5 times every 24 h, respectively, and the cumulative mortality rate of the shrimp at 144 h was 50% after consecutive 5-times changes of the drug. Sampling live shrimps every 8 h after continuous dressing change, WSSVDMSOIn the treatment group, the virus content in the shrimp bodies gradually increased with the time, and in the C5-WSSV treatment group, the virus content in the shrimp bodies was always lower than that in the WSSVDMSOGroups were treated and showed an overall downward trend.
The results of the water stability test of C5 are shown in fig. 6. After the C5 is dissolved in the aquaculture water, the inhibition rate of the virus copy number is not obviously different from that of the freshly prepared C5 after 1 d or 2 d of the C5 is placed at 28 ℃. In the WSSV treatment group, the cumulative mortality rate of the shrimps in 72 h is 100%, and in WSSVC5-0 d、WSSVC5-1 d、WSSVC5-2 d、WSSVC5-3 dAnd WSSVC5-4 dIn the treatment groups, the time for 100% cumulative mortality of the shrimps was 120 h, 108 h, 96 h and 72 h, respectively, and it was found that C5 was likely to be degraded in the culture water and its antiviral effect was gradually reduced as the time in the culture water was prolonged.
The above description is not intended to limit the present invention, and the present invention is not limited to the above examples. Those skilled in the art should also realize that changes, modifications, additions and substitutions can be made without departing from the true spirit and scope of the invention.
Claims (4)
1. The application of the chromene coumarin derivative containing fluorine functional groups in preparing the medicines for inhibiting the white spot syndrome virus is characterized in that the structure of the coumarin derivative is shown as the formula I:
。
2. the application of the chromene coumarin derivative containing the fluorine functional group in the preparation of the white spot syndrome virus inhibiting medicine according to claim 1 is characterized in that the preparation method of the coumarin derivative comprises the following steps: biginelli reaction is carried out on 4-hydroxycoumarin, p-fluorobenzaldehyde and malononitrile to prepare 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene.
3. The application of the chromene coumarin derivative containing the fluorine functional group in the preparation of the white spot syndrome virus inhibiting medicine according to claim 2 is characterized in that the preparation method of the coumarin derivative comprises the following specific steps: placing 2 mmol 4-hydroxycoumarin, 3 mmol p-fluorobenzaldehyde, 2 mmol malononitrile and 0.1 mmol sodium dodecyl sarcosinate in a round bottom flask, adding 10 mL water as a solvent, stirring for 5H at 60-65 ℃, after the reaction is finished, filtering and removing water to obtain a crude product, and recrystallizing the crude product by dichloromethane to obtain 4-fluorophenyl-3-cyano-2-amino-5-deoxy-4H, 5H-pyrone [3,2-c ] chromene, wherein the structure of the chromene is shown as a formula I:
4. the application of the chromene coumarin derivative containing fluorine functional groups according to claim 1 in preparation of medicines for inhibiting white spot syndrome virus.
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| CN106279083A (en) * | 2016-08-02 | 2017-01-04 | 浙江大学 | A kind of furocoumarin analog derivative and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106279083A (en) * | 2016-08-02 | 2017-01-04 | 浙江大学 | A kind of furocoumarin analog derivative and preparation method thereof |
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| Abbas Ali Jafari等.High yield room temperature synthesis of pyranochromenes in neutral cetyltrimethylammonium bromide micellar media.《Environ Chem Lett》.2015,第14卷(第2期),全文. * |
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