CN105622379A - 2,4-DAPG (2,4-Diacetylphloroglucinol) analogue and preparation method and application thereof - Google Patents

2,4-DAPG (2,4-Diacetylphloroglucinol) analogue and preparation method and application thereof Download PDF

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CN105622379A
CN105622379A CN201610147829.3A CN201610147829A CN105622379A CN 105622379 A CN105622379 A CN 105622379A CN 201610147829 A CN201610147829 A CN 201610147829A CN 105622379 A CN105622379 A CN 105622379A
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phloroglucinol
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CN105622379B (en
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龚亮
谭海波
蒋跃明
段学武
杨宝
张丹丹
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South China Botanical Garden of CAS
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    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
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Abstract

The invention discloses a 2,4-DAPG analogue and a preparation method and application thereof. The structure of the 2,4-DAPG analogue is shown as the formula (1) or formula (2), wherein R is C2-C15 alkyl, R1 and R2 are C1-C15 alkyl, and the R1 and the R2 are different. The 2,4-DAPG analogue has excellent activity to resist penicillium italicum, penicillium digitatum, geotrichum citri-aurantii or fusarium moniliforme, the invention further provides a convenient method for synthesizing the 2,4-DAPG analogue, and the 2,4-DAPG analogue has excellent activity to resist penicillium italicum, penicillium digitatum, geotrichum citri-aurantii or fusarium moniliforme, so that the 2,4-DAPG analogue can be used for preparing antibacterial agents, and particularly for application in preventing and curing orange and banana main diseases.

Description

2,4-diacetyl similar thing of base Phloroglucinol and its preparation method and application
Technical field:
The invention belongs to fresh-keeping field, it is specifically related to 2,4-diacetyl similar thing of base Phloroglucinol and its preparation method and application.
Background technology:
2,4-diacetyl base Phloroglucinol (2,4-Diacetylphloroglucinol, 2,4-DAPG, the MP10 in formula (5)) is a kind of phenolic compound, is the secondary metabolite that Pseudomonas fluorescens produces. Studies have found that, plant pathogen is had antibiosis by this kind of meta-bolites, is the important functional factor (Haasetal., Annu.Rev.Phytopathol.2003,41:117-153) of Pseudomonas biocontrol microorganisms.
Summary of the invention:
First object of the present invention is to provide the 2,4-diacetyl similar thing of base Phloroglucinol with the significant mycelial growth suppressing Penicillium italicum bacterium, citrus common green mold bacterium, citric acid maize ear rot bacterium and banana crown rot bacterium.
The 2,4-diacetyl similar thing of base Phloroglucinol of the present invention, its structure is such as formula shown in (1) or formula (2):
Wherein R is C2-C15Alkyl, R1��R2For C1-C15Alkyl, and R1And R2Different.
Arbitrary compound that the described 2,4-diacetyl similar thing of base Phloroglucinol is preferably in formula (3):
Further preferably, the described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
2nd object of the present invention is to provide the preparation method of a kind of 2,4-diacetyl similar thing of base Phloroglucinol, it is characterised in that, its building-up process is as follows:
Being obtained by reacting the compound shown in formula (1) under the catalysis of methylsulfonic acid (MSA) with Phloroglucinol and alkyl acyl chloride, wherein R is C2-C15Alkyl;
Under the catalysis of methylsulfonic acid (MSA), the compound shown in formula (2) it is obtained by reacting, wherein R with single acyl group Phloroglucinol and alkyl acyl chloride1��R2For C1-C15Alkyl, and R1And R2Different.
3rd object of the present invention is to provide the application of the above-mentioned 2,4-diacetyl similar thing of base Phloroglucinol in preparation antibacterials.
Described antibacterials are the medicine of anti-Penicillium italicum bacterium, citrus common green mold bacterium, citric acid maize ear rot bacterium or banana crown rot bacterium.
The described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
4th object of the present invention is to provide the above-mentioned 2,4-diacetyl similar thing of base Phloroglucinol and is preparing oranges and tangerines or banana fresh-keeping agent, or the application prevented and treated in citric acid maize ear rot medicine.
The described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
The present invention provides 2 that a class has better anti-Penicillium italicum bacterium, citrus common green mold bacterium, citric acid maize ear rot bacterium or banana crown rot bacterium activity; the 4-diacetyl similar thing of base Phloroglucinol; and provide a kind of synthesis above-mentioned 2; the short-cut method of the 4-diacetyl similar thing of base Phloroglucinol; due to the 2 of the present invention; it is active that the 4-diacetyl similar thing of base Phloroglucinol has good anti-Penicillium italicum bacterium, citrus common green mold bacterium, citric acid maize ear rot bacterium or banana crown rot bacterium; therefore may be used for preparation antibacterials, especially application on control oranges and tangerines and the main disease of banana.
Embodiment:
Following examples are the further explanations to the present invention, instead of limitation of the present invention.
The preparation method of the embodiment 1:2,4-diacetyl similar thing of base Phloroglucinol:
The building-up process of the 2,4-diacetyl similar thing of base Phloroglucinol of the present invention is as follows:
With Phloroglucinol and alkyl acyl chloride under the catalysis of methylsulfonic acid (MSA), within 3 hours, being obtained by reacting the compound shown in formula (1) through heating, wherein R is C1-C15Alkyl;
React under the catalysis of methylsulfonic acid (MSA) with single acyl group Phloroglucinol and alkyl acyl chloride, within 3 hours, obtain the compound shown in formula (2), wherein R through heating1��R2For C1-C15Alkyl, and R1And R2Different.
Concrete steps are as follows:
(1) round-bottomed flask that Phloroglucinol (315mg, 2.5mmol) and acyl chlorides (5.0mmol) are placed in 10mL drying, is heated to 80 DEG C. Stir after 10 minutes, slowly drip in reaction system and add methylsulphonic acid (25mmol, 1.6Ml). Continue to keep stirring reaction system 3 hours at temperature, then it is chilled to room temperature. Reaction mixture is poured in 25mL frozen water, and extract 3 times by ethyl acetate (25mL), merge organic phase, and respectively with 25mL saturated sodium bicarbonate and brine It. Organic phase is filtered after anhydrous sodium sulfate drying, and gained filtrate is spin-dried in reduced pressure. Remaining oily mixture, through rapid column chromatography (normal hexane: ethyl acetate=5:1) separation, obtains corresponding acyl group Phloroglucinol compound.
Described acyl chlorides
When R is iPr time, gained compound is the MP1 in formula (5);
When R is C8H17During straight chained alkyl, gained compound is the MP2 in formula (5);
When R is C3H7Straight chained alkyl (CH3CH2CH2-) time, gained compound is the MP4 in formula (5);
When R is C7H15During straight chained alkyl, gained compound is the MP5 in formula (5);
When R is iBu, gained compound is the MP7 in formula (5);
When R is cyclopropyl, gained compound is the MP8 in formula (5);
When R is PhC2H4Time, gained compound is the MP9 in formula (5);
When R is CH3Time, gained compound is the MP10 in formula (5);
When R is C11H21During straight chained alkyl, gained compound is the MP11 in formula (5);
When R is C4H9During straight chained alkyl, gained compound is the MP12 in formula (5);
When R is C5H11During straight chained alkyl, gained compound is the MP13 in formula (5);
When R is phenyl, gained compound is the MP14 in formula (5);
When R is C2H5Time, gained compound is the MP15 in formula (5).
(2) round-bottomed flask that ethanoyl Phloroglucinol (336mg, 2.0mmol) and acyl chlorides (3.0mmol) are placed in 10mL drying, is heated to 80 DEG C. Stir after 10 minutes, slowly drip in reaction system and add methylsulphonic acid (15mmol, 1.0mL). Continue to keep stirring reaction system 3 hours at temperature, then it is chilled to room temperature. Reaction mixture is poured in 25mL frozen water, and extract 3 times by ethyl acetate (25mL), merge organic phase, and respectively with 25mL saturated sodium bicarbonate and brine It. Organic phase is filtered after anhydrous sodium sulfate drying, and gained filtrate is spin-dried in reduced pressure. Remaining oily mixture, through rapid column chromatography (normal hexane: ethyl acetate=5:1) separation, obtains corresponding acyl group Phloroglucinol compound.
Described acyl chlorides
Described R2For C5H11Straight chained alkyl (CH3CH2CH2CH2CH2-) time, gained compound is the MP3 in formula (5);
Described R2For C3H7Straight chained alkyl (CH3CH2CH2-) time, gained compound is the MP6 in formula (5).
The nuclear magnetic data of compound MP1-MP15 is as follows:
1, compound MP10
1,1'-(2,4,6-trihydroxy-1,3-phenylene)diethanoneMP10
1HNMR(500MHz,CD3OH+CDCl3): ��=5.75 (s, 1H), 2.60 (s, 6H);13CNMR(125MHz,CDCl3): ��=203.2,170.6,168.2,103.0,93.8,31.3.
2, compound MP15
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(propan-1-one)MP15
1HNMR(500MHz,CDCl3): ��=5.83 (s, 1H), 3.16 (q, J=7.2Hz, 3H), 1.20 (t, J=7.2Hz, 5H);13CNMR(125MHz,CDCl3): ��=171.8,95.3,37.4,31.0,8.5.
3, compound MP6
1-(3-acetyl-2,4,6-trihydroxyphenyl)hexan-1-oneMP6
1HNMR(500MHz,CDCl3): ��=5.83 (d, J=3.4Hz, 1H), 3.10 (t, J=7.2Hz, 2H), 2.72 (s, 3H), 1.72 (q, J=7.4Hz, 2H), 1.02 (t, J=7.4Hz, 3H);13CNMR(125MHz,CDCl3): ��=204.2,172.0,95.2,46.0,32.8,18.0,13.9.
4, compound MP4
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(butan-1-one)MP4
1HNMR(500MHz,CDCl3): ��=5.87 (s, 1H), 3.08 (t, J=9.2Hz, 4H), 1.73 (3,4H), 1.01 (t, J=7.4Hz, 6H);13CNMR(125MHz,CDCl3): ��=207.1,172.0,104.1,95.3,46.0,18.0,13.9.
5, compound MP3
1-(3-acetyl-2,4,6-trihydroxyphenyl)hexan-1-oneMP3
1HNMR(500MHz,CDCl3): ��=5.86 (s, 1H), 3.10 (t, J=7.5Hz, 2H), 2.72 (s, 3H), 1.70 (m, 2H), 1.37 (m, 4H), 0.99 (m, 3H);13CNMR(125MHz,CDCl3): ��=207.3,204.4,172.1,104.1,95.3,44.1,32.8,31.6,24.3,22.6,14 .0.
6, compound MP1
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(2-methylpropan-1-one)MP1
1HNMR(500MHz,CDCl3): ��=5.87 (s, 1H), 3.96 (t, J=6.7Hz, 1H), 1.21 (d, J=6.7Hz, 1H);13CNMR(125MHz,CDCl3): ��=211.5,182.4,172.2,103.6,95.6,39.3,19.2.
7, compound MP8
(2,4,6-trihydroxy-1,3-phenylene)bis(cyclopropylmethanone)MP8
1HNMR(500MHz,CDCl3): ��=5.78 (s, 1H), 4.17 (s, 2H), 2.0-2.5 (m, 8H);13CNMR(125MHz,CDCl3): ��=169.6,95.3,45.0,24.7,21.2.
8, compound MP12
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(pentan-1-one)MP12
1HNMR(500MHz,CDCl3): ��=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J=15.0,7.5Hz, 4H), 1.42 (dd, J=15.0,7.5Hz, 4H), 0.97 (t, J=7.5Hz, 6H).13CNMR(125MHz,CDCl3): ��=207.3,172.0,95.4,43.9,26.8,24.5,14.0.
9, compound MP7
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(3-methylbutan-1-one)MP7
1HNMR(500MHz,CDCl3): ��=5.87 (s, 1H), 2.99 (d, J=6.7Hz, 4H), 2.27 (m, 2H), 1.00 (d, J=6.7Hz, 6H);13CNMR(125MHz,CDCl3): ��=206.8,179.2,172.1,104.3,95.4,43.1,25.6,22.8.
10, compound MP13
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(hexan-1-one)MP13
1HNMR(500MHz,CDCl3): ��=5.83 (s, 1H), 3.10 (t, J=7.4Hz, 4H), 1.71 (m, 4H), 1.37 (m, 8H), 0.93 (m, 6H);13CNMR(125MHz,CDCl3): ��=171.9,95.4,44.1,31.6,24.4,22.6,14.0.
11, compound MP14
(2,4,6-trihydroxy-1,3-phenylene)bis(cyclohexylmethanone)MP14
1HNMR(500MHz,CDCl3): ��=5.79 (s, 1H), 4.44 (s, 4H);13CNMR(125MHz,CDCl3): ��=204.1,172.1,134.7,129.9,128.5,126.9,95.7,50.1.
12, compound MP5
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(octan-1-one)MP5
1HNMR(500MHz,CDCl3): ��=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J=15.0,7.5Hz, 4H), 1.31 (m, 16H), 0.90 (t, J=7.5Hz, 6H).13CNMR(125MHz,CDCl3): ��=207.3,172.0,95.4,44.5,31.8,29.5,29.2,29.1,25.1,14.1.
13, compound MP2
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(octan-1-one)MP2
1HNMR (500MHz, CDCl3): ��=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J=15.0,7.5Hz, 4H), 1.31 (m, 20H), 0.90 (t, J=7.5Hz, 6H).13CNMR(125MHz,CDCl3): ��=207.3,172.0,95.4,44.3,31.8,29.6,29.5,29.2,29.1,25.0,14.1.
14, compound MP9
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(2-phenylethanone)MP9
1HNMR(500MHz,CDCl3): ��=7.20-7.40 (m, 10H), 5.79 (s, 1H), 4.44 (s, 4H);13CNMR(125MHz,CDCl3): ��=204.1,172.1,134.7,129.9,128.5,126.9,95.7,50.1.
15, compound MP11
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(dodecan-1-one)MP11
1HNMR(500MHz,CDCl3): ��=5.81 (s, 1H), 3.10 (t, J=7.4Hz, 4H), 1.70 (m, 4H), 1.31 (m, 32H), 0.90 (t, J=7.5Hz, 6H).13CNMR(125MHz,CDCl3): ��=171.9,95.4,44.2,31.9,29.6,29.6,29.5,29.3,29.2,29.1,24.7,22.7,14.1.
Embodiment 2:
Medicament (compound MP4, compound MP6 or compound MP10) is dissolved in DMSO, with PDA substratum is diluted to 25 �� g/ml, then the culture dish of 9cm it is placed in, culture dish central authorities inoculation oranges and tangerines green mold bacterium, observe 7 days, with group of solvents in contrast, according to following formulae discovery inhibiting rate.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length �� 100%
Result shows: the inhibiting rate of oranges and tangerines green mold is 80% and 84% by compound MP6 and compound MP4 respectively, is significantly higher than the inhibiting rate of female parent (2,4-DAPG, i.e. compound MP10) 29.7%.
Embodiment 3:
Medicament (compound MP4, compound MP6 or compound MP10) is dissolved in DMSO, further with PDA substratum is diluted to 25 �� g/ml, then the culture dish of 9cm it is placed in, at culture dish central authorities inoculation oranges and tangerines Penicillium notatum, observe 7 days, with group of solvents in contrast, according to following formulae discovery inhibiting rate.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length �� 100%
Result shows: the inhibiting rate of oranges and tangerines Penicillium notatum is 59.3% and 63% by compound MP6 and compound MP4 respectively, is significantly higher than the inhibiting rate of female parent (2,4-DAPG, i.e. compound MP10) 40.7%.
Embodiment 4:
Medicament (compound MP1 or compound MP10) is dissolved in DMSO, further with PDA substratum is diluted to 25 �� g/ml, then the culture dish of 9cm it is placed in, culture dish central authorities inoculation banana crown rot bacterium, observe 7 days, with group of solvents in contrast, according to following formulae discovery inhibiting rate.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length �� 100%;
Result shows: the inhibiting rate of banana crown rot bacterium is 75.4% by compound MP1, is significantly higher than the inhibiting rate of female parent (2,4-DAPG) 51.8%.
Embodiment 5:
Medicament (compound MP14 or compound MP10) is dissolved in DMSO, further with PDA substratum is diluted to 25 �� g/ml, then the culture dish of 9cm it is placed in, culture dish central authorities inoculation citric acid maize ear rot bacterium, observe 7 days, with group of solvents in contrast, according to following formulae discovery inhibiting rate.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length �� 100%;
Result shows: the inhibiting rate of citric acid maize ear rot bacterium is 69.4% by compound MP14, is significantly higher than the inhibiting rate of female parent (2,4-DAPG) 31.8%.

Claims (9)

  1. The 1.2,4-diacetyl similar thing of base Phloroglucinol, its structure is such as formula shown in (1) or formula (2):
    Wherein R is C2-C15Alkyl, R1��R2For C1-C15Alkyl, and R1And R2Different.
  2. 2. the 2,4-diacetyl similar thing of base Phloroglucinol according to claim 1, it is characterised in that, the described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (3):
  3. 3. the 2,4-diacetyl similar thing of base Phloroglucinol according to claim 2, it is characterised in that, the described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
  4. 4. the 2,4-diacetyl similar thing of base Phloroglucinol according to claim 1 is in the application prepared in antibacterials.
  5. 5. application according to claim 5, it is characterised in that, described antibacterials are the medicine of anti-Penicillium italicum bacterium, citrus common green mold bacterium, citric acid maize ear rot bacterium or banana crown rot bacterium.
  6. 6. application according to claim 4 or 5, it is characterised in that, the described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
  7. 7. the 2,4-diacetyl similar thing of base Phloroglucinol according to claim 1 is preparing oranges and tangerines or banana fresh-keeping agent, or the application prevented and treated in citric acid maize ear rot medicine.
  8. 8. application according to claim 7, it is characterised in that, the described 2,4-diacetyl similar thing of base Phloroglucinol is the arbitrary compound in formula (4):
  9. 9. the preparation method of the 2,4-diacetyl similar thing of base Phloroglucinol, it is characterised in that, its building-up process is as follows:
    Being obtained by reacting the compound shown in formula (1) under the catalysis of methylsulfonic acid with Phloroglucinol and alkyl acyl chloride, wherein R is C2-C15Alkyl;
    Under the catalysis of methylsulfonic acid, the compound shown in formula (2) it is obtained by reacting, wherein R with single acyl group Phloroglucinol and alkyl acyl chloride1��R2For C1-C15Alkyl, and R1And R2Different.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106905157A (en) * 2017-01-10 2017-06-30 西北农林科技大学 2,4 diacetyl phloroglucin ester type compounds and its application of sterilization
CN107501287A (en) * 2017-08-22 2017-12-22 中国科学院华南植物园 Myrtuco mmulone J and Myrtucommuacetalone and the like preparation method
CN109456927A (en) * 2018-11-14 2019-03-12 中国科学院青岛生物能源与过程研究所 The recombinant bacterium and its construction method of a kind of high yield 2,4- diacetyl phloroglucin and application

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