CN113912484B - 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat - Google Patents
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat Download PDFInfo
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- 229940076442 9,10-anthraquinone Drugs 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 32
- 241000186810 Erysipelothrix rhusiopathiae Species 0.000 claims description 6
- 241000194021 Streptococcus suis Species 0.000 abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 11
- 201000000297 Erysipelas Diseases 0.000 abstract description 5
- 241000193830 Bacillus <bacterium> Species 0.000 abstract description 2
- 239000000022 bacteriostatic agent Substances 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 abstract description 2
- 241000191940 Staphylococcus Species 0.000 abstract 1
- 239000000273 veterinary drug Substances 0.000 abstract 1
- 241000191967 Staphylococcus aureus Species 0.000 description 10
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- -1 anthraquinone compounds Chemical class 0.000 description 5
- 208000022362 bacterial infectious disease Diseases 0.000 description 5
- 208000035143 Bacterial infection Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 229940124350 antibacterial drug Drugs 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- YQYBUJYBXOVWQW-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 YQYBUJYBXOVWQW-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/16—Quinones the quinoid structure being part of a condensed ring system containing three rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to the technical field of pharmaceutical chemistry, and particularly discloses a 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of a bacteriostatic agent, wherein an antibacterial activity test shows that the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound can obviously inhibit staphylococcus aureusStaphylococcus aureus) Bacillus erysipelas of pigErysipelothrix rhusiopathiae) And Streptococcus suis @Streptococcus suis) Has application as preparation of new antibacterial veterinary drugs.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of a bacteriostatic agent.
Background
Bacterial infections continue to be an important threat to human and animal health. Streptococcus suis (Streptococcus suis) is an important bacterial infectious disease pathogen, has the characteristics of wide epidemic and strong pathogenicity, is an important infectious disease pathogen for human and animals, can cause various diseases of various animals including human and pigs, causes infection and even death, and seriously affects the development of pig industry and human health. Erysipelothrix rhusiopathiae is a pathogenic bacterium of erysipelas in pigs, and can cause infection of people, birds, lambs and the like by accident, and the erysipelas can occur after the infection of people. Antibiotics play an important role in controlling bacterial infection, and the appearance of clinical multi-drug resistant strains and super-drug resistant bacteria indicate that the existing anti-bacterial infection medicines can not meet the requirements of animals and human for preventing and controlling bacterial infection, so that research on new anti-bacterial medicines is urgently needed.
8 1,4, 6-trihydroxy-8-branched anthraquinone compounds (compounds 1-8) are obtained in the early stage of the applicant, and the series of compounds are found to have better antitumor activity [ Wu Zhaoyuan and the like, anthraquinone Analogues from a Soil ActinomyceteStreptomyces sp.WS-13394and their bioactivities.Natural Product Research,2018,32 (4): 412-417; wu Zhaoyuan et al, new Cytotoxic Alkylated Anthraquinone Analogues from a Soil ActinomyceteStreptomyces sp.WS-13394.Chemical&Pharmaceutical Bulletin,2014,62 (1): 118-121 ].
On the basis of the structure of the compound 1-8, the applicant further obtains the compound 9-11, and discovers that the compound 1-11 has obvious growth inhibition effect on bacteria, particularly staphylococcus aureus, erysipelas Sus bacillus and streptococcus suis, and has not been reported in the literature at home and abroad.
Disclosure of Invention
The invention aims to provide a 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound, which has the following structural formula:
wherein R is: propyl, butyl, isopentyl, pentyl, pentylcarboxyl, 2' -carbonylpentyl, 2' -carbonylhexyl, hexyl, 2' -hydroxypropyl, 4' -hydroxyisopentyl or 2' -hydroxypentyl.
Another object of the present invention is to provide an application of 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compounds in preparing bacterial bacteriostats.
In order to achieve the above object, the present invention adopts the following technical measures:
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound, the structural formula of the compound is as follows:
wherein R is: propyl, butyl, isopentyl, pentyl, pentylcarboxyl, 2' -carbonylpentyl, 2' -carbonylhexyl, hexyl, 2' -hydroxypropyl, 4' -hydroxyisopentyl or 2' -hydroxypentyl.
When R is different groups, the compounds are named as the compounds 1-11 in sequence, and specifically, the structural formulas of the compounds 1-11 are as follows:
the protection scope of the invention also comprises: application of the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound in preparing bacteria inhibitor.
In the above applications, preferably, the bacteria are staphylococcus aureus (Staphylococcus aureus), erysipelothrix rhusiopathiae (erysiphe necator), and/or streptococcus suis (Streptococcus suis).
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. the antibacterial agents currently used clinically are mainly cyclic peptides, macrolides and penicillins. The structure of the invention is completely different from the framework type of the antibacterial drugs used clinically at present, and the invention is a 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound. The antibacterial drugs further developed based on the compounds can completely avoid the existing drug patents on the market, and provide more choices for the market.
2. The invention discovers novel compounds 9-11, and discovers that the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compounds have the activity of resisting staphylococcus aureus, streptococcus suis and erysipelas suis for the first time.
3. The antibacterial experiment results show that the compounds 1, 2, 4, 5, 8 and 10 have remarkable antibacterial activity (MIC <0.78 mug/mL) on staphylococcus aureus, and the compounds 3, 6, 9 and 11 also have stronger antibacterial activity (MIC is 6.25, 1.56, 0.78 and 1.56 mug/mL respectively) on staphylococcus aureus; compounds 3, 9 and 10 have strong antibacterial activity against erysipelothrix rhusiopathiae (MIC 3.125, 6.25 and 3.125 μg/mL, respectively); compounds 1, 2, 3, 4and 8 have potent antimicrobial activity against Streptococcus suis (MIC 6.25, 3.125, 6.25, 3.125 and 1.56. Mu.g/mL, respectively). Therefore, the 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound has potential application in preparing novel antibacterial drugs.
Detailed Description
The invention is further illustrated in detail below in connection with specific examples which are provided solely for the purpose of illustration and are not intended to limit the scope of the invention. The test methods used in the following examples are conventional methods unless otherwise specified; the materials, reagents and the like used, unless otherwise specified, are those commercially available.
Example 1:
1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound, the structural formula of the compound is as follows:
wherein R is: propyl, butyl, isopentyl, pentyl, pentylcarboxyl, 2' -carbonylpentyl, 2' -carbonylhexyl, hexyl, 2' -hydroxypropyl, 4' -hydroxyisopentyl or 2' -hydroxypentyl.
When R is different groups, the compounds are named as the compounds 1-11 in sequence, and specifically, the structural formulas of the compounds 1-11 are as follows:
among them, the applicant of the compounds 1 to 8 has reported that the structural identification of the compounds 9 to 11 has the following UV, HR-ESI-MS and NMR spectrum data:
compounds 9-11 were all red powders and a common UV absorption ultraviolet absorption spectrum (466, 277, 225 nm) indicated that these compounds all had a common 1,4,6, 8-substituted anthraquinone backbone.
HR-ESI-MS data: compound 9 (M/z 337.0688, [ M+Na ]] + ) Deducing that its molecular formula is C 17 H 14 O 6 . Compound 10 (M/z 365.0994, [ M+Na ]] + ) Deducing that its molecular formula is C 19 H 18 O 6 The method comprises the steps of carrying out a first treatment on the surface of the Compound 11 (M/z 365.0994, [ M+Na ]] + ) Deducing that its molecular formula is C 19 H 18 O 6 。
NMR data were as follows:
TABLE 1 Compounds 9-11 (DMSO-d 6) 1 H-NMR (500 MHz) data (. Delta. H ,J Hz)
TABLE 2 Compounds 9-11 (DMSO-d 6) 13 C-NMR data (125 MHz) data
Example 2:
test of antibacterial Activity of Compounds 1-11:
selecting staphylococcus aureus (Staphylococcus aureus), erysipelothrix rhusiopathiae (Erysipelotohrix rhusiopathiae) and streptococcus suis (Streptococcus suis), escherichia coli (Escherichia coli) and pseudomonas aeruginosa (Pseudomonas aeruginosa) strains, subculturing on a nutrient agar slant culture medium for 1 time, inoculating the strains into a nutrient broth culture medium, culturing for 6-12 hours at 37 ℃, and placing the culture medium in a refrigerator for standby. Taking a sample to be tested and positive control (streptomycin and penicillin), sequentially diluting to 100 mug/mL, 50 mug/mL, 25 mug/mL, 12.5 mug/mL, 6.25 mug/mL, 3.125 mug/mL, 1.56 mug/mL and 0.78 mug/mL by using a culture solution, shaking and mixing, taking 1mL, transferring to a 96-well plate, taking a culture medium as a blank control, selecting 3 repeats for the blank and each concentration, culturing for 3 times at 37 ℃ for 12-18 hours, measuring absorbance by using an enzyme-labeled instrument of 630nm, and determining the MIC value.
Results: compounds 1, 2, 4, 5, 8 and 10 have significant antimicrobial activity against Staphylococcus aureus (MIC < 0.78. Mu.g/mL), and compounds 3, 6, 9 and 11 also have stronger antimicrobial activity against Staphylococcus aureus (MIC 6.25, 1.56, 0.78 and 1.56. Mu.g/mL, respectively); compounds 3, 9 and 10 have strong antibacterial activity against erysipelothrix rhusiopathiae (MIC 3.125, 6.25 and 3.125 μg/mL, respectively); compounds 1, 2, 3, 4and 8 have potent antimicrobial activity against Streptococcus suis (MIC 6.25, 3.125, 6.25, 3.125 and 1.56. Mu.g/mL, respectively).
Table 3 inhibition of three bacteria by Compounds 1-11 (MIC. Mu.g/ml)
"-" means that the drug concentration is less than 100 mug/ml and no antibacterial activity exists
The above-described embodiments are only for illustration and are not intended to limit the scope of the present invention. Various modifications and adaptations of the invention will occur to those skilled in the art and such equivalent variations are intended to be within the scope of the invention as defined in the claims.
Claims (1)
- Application of 1.1,4,6-trihydroxy-8-branched-9, 10-anthraquinone compound in preparation of erysipelothrix rhusiopathiae bacteriostat, wherein the structural formula of the compound is as follows:
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| CN202110675730.1A CN113912484B (en) | 2021-06-18 | 2021-06-18 | 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat |
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| CN202110675730.1A CN113912484B (en) | 2021-06-18 | 2021-06-18 | 1,4, 6-trihydroxy-8-branched-9, 10-anthraquinone compound and application thereof in preparation of bacteriostat |
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|---|---|---|---|---|
| JPH0769872A (en) * | 1993-09-02 | 1995-03-14 | Gifu Seratsuku Seizosho:Kk | Anti-methicilin resistant staphylococcus agent |
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-
2021
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|---|
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