CN113730405A - Application of bispyridone hydrazone-4-indole formaldehyde Schiff base - Google Patents
Application of bispyridone hydrazone-4-indole formaldehyde Schiff base Download PDFInfo
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- CN113730405A CN113730405A CN202111096167.9A CN202111096167A CN113730405A CN 113730405 A CN113730405 A CN 113730405A CN 202111096167 A CN202111096167 A CN 202111096167A CN 113730405 A CN113730405 A CN 113730405A
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- hydrazone
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 26
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 6
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 4
- 241000588724 Escherichia coli Species 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 4
- 201000007270 liver cancer Diseases 0.000 claims abstract description 3
- 208000014018 liver neoplasm Diseases 0.000 claims abstract description 3
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 5
- UWDHESVDMJZCAI-UHFFFAOYSA-N 2-pyridin-2-yl-4h-pyridin-3-one Chemical compound O=C1CC=CN=C1C1=CC=CC=N1 UWDHESVDMJZCAI-UHFFFAOYSA-N 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000035755 proliferation Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 150000004753 Schiff bases Chemical class 0.000 abstract description 16
- -1 bipyridone hydrazone Chemical class 0.000 abstract description 13
- 150000007857 hydrazones Chemical class 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 4
- 229940124350 antibacterial drug Drugs 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003746 solid phase reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 210000003953 foreskin Anatomy 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- IDBOAVAEGRJRIZ-UHFFFAOYSA-N methylidenehydrazine Chemical compound NN=C IDBOAVAEGRJRIZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
-
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to the field of pharmaceutical chemistry, in particular to application of Schiff base generated by reaction of bipyridone hydrazone and 4-indole formaldehyde in anticancer drugs, antibacterial drugs or antibacterial materials. The system is named as the Schiff base generated by the reaction of bipyridone hydrazone and 4-indole formaldehyde: 4- ((di (pyridin-2-yl) methylene) hydrazone) methyl) -1H-indole with the molecular formula C20H15N5(ii) a The appearance of the Schiff base is dark brown blocky crystal, and the melting point is 180-182 ℃; the structure is as follows:
. The chemical conversion is carried outCompound on mouse breast cancer cell 4T1The IC50 (half inhibition concentration of the drug) is 57.2 mu M, the IC50 of human liver cancer Hep G2 cells is 36.4 mu M, and the drug has better tumor inhibition activity; and can effectively inhibit the propagation of escherichia coli and staphylococcus aureus.
Description
Technical Field
The invention relates to the field of medicinal chemistry, in particular to application of Schiff base generated by reaction of bispyridone hydrazone and 4-indole formaldehyde in anticancer drugs, antibacterial drugs or antibacterial materials. .
Background
Schiff base is a compound containing an imine or azomethine group, of the general formula R1R2C=NR3. The Schiff base ligand with various structures and functions can be synthesized by introducing different substituent groups through the reaction design of a compound of an active carbonyl group and different amine compounds. Schiff base has many well-known obvious biological activities, such as antibiosis, antifungal, weeding, antituberculosis, anti-HIV, anticancer and the like, which makes it widely used in the fields of medicinal chemistry, functional materials and the like. In addition, the Schiff base with a large conjugated system often has good fluorescence property, and is widely applied to the fields of organic pigments, optical brighteners, photo-oxidizers, coatings, chemical and biochemical analysis, solar collectors, anti-counterfeiting marks, drug tracing, lasers and the like. .
Disclosure of Invention
The invention relates to a synthetic method of Schiff base, namely the Schiff base generated by the reaction of bispyridone hydrazone and 4-indole formaldehyde, which is systematically named as follows: 4- ((di (pyridin-2-yl) methylene) hydrazone) methyl) -1H-indole with the molecular formula C20H15N5(ii) a The appearance of the Schiff base is dark brown blocky crystal, and the melting point is 180-182 ℃; the structure is as follows.
And identifying the structure.
Elemental analysis of the bipyridone hydrazone-4-indole carbaldehyde Schiff base showed that C, H, N% respectively are 73.84%, 4.64% and 21.53% (theoretical values are 73.83%, 4.65% and 21.52%, respectively), and the molecular weight is 325.375; the analysis of the single crystal structure shows that the crystal is monoclinic,P21/nspatial groups, a =9.7321(8) a, b = 9.7080(7) a, c = 18.6699(13) a, α = γ =90 °, β =94.252(7) ° V =1759.1(2) a3Z =4, related1HNMR spectrum,13The CNMR spectra are shown in figure 1 and figure 2 respectively;the structure diagram and the stacking diagram of the single crystal structure are shown in the attached figures 3 and 4 respectively.
And a synthetic method.
The bipyridyl ketone hydrazone-4-indole formaldehyde Schiff base has two synthesis methods: the first method takes bipyridone hydrazone and 4-indole formaldehyde as raw materials and comprises the following steps.
1) Dissolving the dipyridone hydrazone in a proper organic solvent, adding the 4-indolylaldehyde according to a certain substance amount ratio, and stirring and reacting at a certain temperature for a certain time to complete the reaction.
The first step can also adopt solid phase reaction, namely organic solvent is not used, the dipyridone hydrazone and the 4-indole formaldehyde are mixed according to a certain substance amount ratio and then are ground and reacted for a certain time at normal temperature, and the obtained solid is the crude product of the target product.
2) If liquid phase reaction is adopted, filtering is carried out after the reaction is finished, and the precipitated dark brown blocky crystals are the target product after the filtrate is naturally volatilized; if solid phase reaction is adopted, the target product can be obtained by recrystallization with proper organic solvent after the reaction is finished.
The second method takes the bipyridone and the 4-indole formaldehyde hydrazone as raw materials, and is completed in one step in a proper organic solvent, and the steps are as follows.
1) Dissolving dipyridone in a proper organic solvent, adding 4-indolylcarbaldehyde hydrazone according to a certain substance amount ratio, and stirring and reacting at a certain temperature for a certain time to complete the reaction; if the solid-phase reaction is adopted, an organic solvent is not used, the two are mixed according to a certain proportion and then the grinding reaction is carried out for a certain time, and the obtained solid is the crude product of the target product.
2) If liquid phase reaction is adopted, filtering is carried out after the reaction is finished, and the precipitated dark brown blocky crystals are the target product after the filtrate is naturally volatilized; if solid phase reaction is adopted, the target product can be obtained by recrystallization with proper organic solvent after the reaction is finished.
The two preparation methods are different mainly in reactants, but the molar ratio of the reaction raw materials is between 4:1 and 1: 4.
The organic solvent (including the solvent for reaction or the solvent for recrystallization) in the above two preparation methods is selected from: methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran, acetone, ethyl acetate, toluene, dioxane, etc.; the solid phase reaction does not use organic solvent, the raw materials react directly, and the solvent used for recrystallization can also be selected from the above solvents.
Preferably, the reaction temperature of the liquid phase reaction is normal temperature or heating reflux, and the reaction method is stirring; the solid phase reaction can be carried out at normal temperature, and the reaction method is grinding.
Preferably, the reaction time is selected from: 0.5-10 h.
The invention has the beneficial effects that: can synthesize more complex functional molecular materials by simpler steps and reactants.
And in vitro antitumor activity.
Mice growing in log phase were breast cancer 4T1The cells or human hepatoma Hep G2 cells were digested with 0.25% pancreatic enzyme to become single cells, and prepared into 1.25X 10 by using 10% fetal bovine serum-containing F12K culture medium7One cell/L suspension of single cells, cells were seeded in 96-well plates at 200. mu.L per well (2.5X 10 per well)3Individual cells). Place 96-well cell culture plates in CO2In an incubator at 37 ℃ with 5% CO2Culturing for 48h under the condition.
When the cells in the wells are full (90% full), adding different doses of Schiff's base solution (200. mu.L/well) according to experimental groups to make the final concentrations of the compounds to be tested respectively 5. mu.M, 10. mu.M, 30. mu.M, 50. mu.M and 100. mu.M, setting 3 multiple wells in each group, and culturing for 96 h.
mu.L of MTT at a concentration of 0.5g/L was added to each well, and the culture was continued for 4 hours to reduce MTT to Formazan (Formazan). After all the supernatants were aspirated, 200. mu.L of DMSO was added to each well, and the mixture was shaken for 15min to dissolve formazan sufficiently, and then absorbance (OD value) at 490nm was measured using an ELISA detector. Then, the calculation was performed as follows.
Cell inhibition% = (control OD value-experimental OD value)/control OD value × 100%.
The test result shows that the bipyridone hydrazone-4-indoleFormaldehyde Schiff base on mouse breast cancer cell 4T1Has an IC50 (half maximal inhibitory concentration of drug) of 57.2. mu.M; IC50 of Hep G2 cell of human liver cancer is 36.4 mu M; the inhibition rate of human foreskin fibroblast HFF-1 is 112.5 mu M; this indicates that the Schiff base molecule has a good inhibitory effect on both cancer cells, but has a low inhibitory rate on normal cells.
And antibacterial activity.
The antibacterial effect is measured by adopting a filter paper diffusion method: soaking circular filter paper sheets (each sheet absorbs 10 microliters of liquid medicine) with the same size and the same diameter of 8mm into DMSO (dimethylsulfoxide) solution of a to-be-detected medicine with the concentration of 100 mug/mL, taking out the filter paper sheets after 30 minutes, airing, wherein the drug-loading capacity of each filter paper sheet is about 1 mug, then placing the filter paper sheets into the center of a plate coated with escherichia coli or staphylococcus aureus, pasting a label on a culture dish cover, marking, placing the culture dish into a constant-temperature incubator, culturing for 24 hours at 37 ℃, measuring the diameter of an antibacterial ring by using a vernier caliper, and comparing with penicillin potassium (the concentration of 10 mug/mL).
Test results show that the diameters of inhibition zones of the bispyridone hydrazone-4-indole formaldehyde Schiff base on escherichia coli/staphylococcus aureus are 25.3 mm and 24.1mm respectively; has approached 29.0 and 28.4mm of potassium penicillin, and shows better bacteriostatic activity.
Detailed Description
In order to better understand the present invention, the following embodiment further illustrates the technical solution of the present invention.
Example 1.
Weighing 1.98g (0.01 mol) of bispyridone hydrazone powder, placing the powder in a 100mL single-neck flask, pouring 30mL of ethanol into the flask, stirring for dissolving, weighing 1.45g (0.01 mol) of 4-indolylaldehyde into the flask after the powder is completely dissolved, heating to 79 ℃, refluxing, stirring for reacting for 8 hours, cooling to room temperature, filtering, placing the filtrate in a beaker for natural volatilization, and obtaining the bispyridone hydrazone-4-indolylaldehyde Schiff base after about 1 week to see that dark brown blocky crystals are formed at the bottom of the beaker, wherein the crystals can be recrystallized by using acetonitrile to obtain a purer product.
Example 2.
Dissolving 1.84g (0.01 mol) of bipyridyl ketone in 30ml of ethanol, adding 1.59g of 4-indolylformaldehyde hydrazone according to the mass ratio of 1:1, heating and refluxing for 3h, cooling to room temperature, filtering, placing the filtrate in a beaker for natural volatilization, and obtaining dark brown blocky crystals after the solvent is volatilized to the residual about 5ml, namely bipyridyl ketone hydrazone-4-indolylformaldehyde Schiff base, and recrystallizing with acetonitrile to obtain a purer product.
Example 3.
1.84g (0.01 mol) of bipyridyl ketone and 1.59g (0.01 mol) of 4-indolylformaldehyde hydrazone are mixed and ground for 8 hours to obtain yellow powdery solid, namely bipyridyl ketone hydrazone-4-indolylformaldehyde Schiff base, and acetonitrile can be used for recrystallization to obtain a purer product.
Drawings
FIG. 1 shows the preparation of bispyridone hydrazone-4-indolecarboxaldehyde Schiff base1H NMR spectrum (solvent DMSO-d 6).
FIG. 2 shows the preparation of bispyridone hydrazone-4-indolecarboxaldehyde Schiff base13CNMR spectrum (solvent DMSO-d 6).
FIG. 3 is a crystal structure diagram of bispyridone hydrazone-4-indole carbaldehyde Schiff base, with an ellipsoid probability of 30%.
FIG. 4 is a packing diagram of the crystal structure of bispyridone hydrazone-4-indolecarboxaldehyde Schiff base with 10% probability of ellipsoid.
Claims (2)
1. The application of the compound shown as the following formula or the pharmaceutically acceptable salt thereof in preparing the medicine for preventing and/or treating tumors is characterized in that: the tumor is breast cancer or liver cancer; the appearance of the bipyridone hydrazone-4-indole formaldehyde Schiff base is dark brown blocky crystal, and the melting point is 180-182 ℃; the structure is as follows:
2. use of a compound as claimed in claim 1 in an antibacterial medicament or material, which is effective in inhibiting the proliferation of escherichia coli or staphylococcus aureus.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110606843A (en) * | 2019-09-30 | 2019-12-24 | 齐鲁工业大学 | Structure, preparation and application of bipyridone hydrazone-2-acetylpyrazine |
| CN110772506A (en) * | 2019-11-12 | 2020-02-11 | 齐鲁工业大学 | Application of benzil hydrazone-1-naphthaldehyde Schiff base |
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- 2021-09-18 CN CN202111096167.9A patent/CN113730405A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110606843A (en) * | 2019-09-30 | 2019-12-24 | 齐鲁工业大学 | Structure, preparation and application of bipyridone hydrazone-2-acetylpyrazine |
| CN110772506A (en) * | 2019-11-12 | 2020-02-11 | 齐鲁工业大学 | Application of benzil hydrazone-1-naphthaldehyde Schiff base |
Non-Patent Citations (1)
| Title |
|---|
| 王迪: "双（2-吡啶）酮腙席夫碱及其金属配合物的合成、结构与性质研究", 中国优秀硕士学位论文全文数据库 工程科技I辑, no. 2, pages 014 - 416 * |
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