CN110577521B - Structure, preparation and application of 2-thiazole formaldehyde-2-pyridine Schiff base - Google Patents
Structure, preparation and application of 2-thiazole formaldehyde-2-pyridine Schiff base Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000002262 Schiff base Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000013078 crystal Substances 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 8
- -1 2- ((E) -pyridin-2-ylmethylene) hydrazono Chemical group 0.000 claims abstract description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- BTWNEJOURYOHME-UHFFFAOYSA-N 1,3-thiazol-2-ylhydrazine Chemical compound NNC1=NC=CS1 BTWNEJOURYOHME-UHFFFAOYSA-N 0.000 claims description 7
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
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- 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
- 201000010881 cervical cancer Diseases 0.000 claims description 3
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
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- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 2
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- 238000010532 solid phase synthesis reaction Methods 0.000 claims 2
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- 238000004519 manufacturing process Methods 0.000 claims 1
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- 230000036961 partial effect Effects 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 8
- FRBSPFFZEASXDY-FNCQTZNRSA-N N1=C(C=CC=C1)\C=N\N=C\C=1SC=CN1 Chemical compound N1=C(C=CC=C1)\C=N\N=C\C=1SC=CN1 FRBSPFFZEASXDY-FNCQTZNRSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000003746 solid phase reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000005764 inhibitory process Effects 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
- 230000003287 optical effect Effects 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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Abstract
The invention relates to a structure, a preparation method and partial properties of a compound crystal. This compound appears as a yellow block with a melting point: 114.8-116.8 deg.C, molecular formula C 10 H 8 N 4 S, the chemical name is: 2- ((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole; the structure of the compound is detailed in the specification, and the compound has certain fluorescence property and anticancer activity.
Description
Technical Field
The invention relates to the fields of organic synthesis, optical materials, pharmaceutical chemistry and the like, and a target product is synthesized in one step by using a simpler method.
Background
At present, with the continuous progress of modern science and technology, people have more and more researches on fluorescence and the fluorescence property of the fluorescence. The fluorescent substance is widely applied to the fields of dyes, organic pigments, optical brighteners, photo-oxidizers, coatings, chemical and biochemical marking analysis, solar collectors, anti-counterfeiting marks, medicine tracing, lasers and the like. The organic fluorescent material is mainly used in the current popular technology, such as fluorescent probes, fluorescence analysis and the like, and is an indispensable material for optical electronic devices, DNA diagnosis, photochemical sensors, laser dyes and organic electroluminescent devices.
Schiff bases are mainly organic compounds containing imine or azomethine characteristic groups (-RC ═ N-), and are usually formed by condensation of amines and active carbonyl groups. Schiff base compounds and metal complexes thereof have important application in the fields of medicine and pharmacology, catalysis, analytical chemistry, corrosion and photochromism. In the medical field, Schiff base has biological activities of bacteriostasis, sterilization, anti-tumor and antivirus; in the field of catalysis, complexes of cobalt, nickel and palladium of schiff bases have been used as catalysts; in the field of analytical chemistry, Schiff bases are used as good ligands and can be used for identifying and identifying metal ions and quantitatively analyzing the content of the metal ions; in the corrosion field, certain aromatic schiff bases are often used as corrosion inhibitors for copper; certain schiff bases containing characteristic groups also have unique applications in the field of photochromism.
Disclosure of Invention
The invention relates to a compound which can be used as fluorescent material and anticancer drug, wherein the compound is yellow block-shaped in appearance, and the melting point is as follows: 114.8-116.8 deg.C, molecular formula C 10 H 8 N 4 S, molecular weight 216.26; the chemical name is: 2- ((E) - (((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole, having the structure:
1. and (3) structural identification:
elemental analysis showed that this compound has the formula C 10 H 8 N 4 S; elemental analysis results (%): the experimental values of C,55.60, H,3.72, N,25.89, S, 15.01; theoretical value: c,55.54, H,3.73, N,25.91, S, 14.82; the analysis of the single crystal structure shows that the crystal belongs to a monoclinic system and the space group is
β＝92.436(13)°，
Z is 4; in connection with 1 The HNMR spectrum is shown in figure 1; FIG. 2 and FIG. 3 are a thermal ellipsoid crystal structure diagram and a crystal structure stacking diagram of the compound, respectively.
2. A synthetic method.
The method one is characterized in that: taking (E) -2- (hydrazono) thiazole and 2-pyridine-formaldehyde as raw materials, and completing the reaction in one step in a proper organic solvent. The method comprises the following steps:
1) dissolving all (E) -2- (hydrazono) thiazole in a proper organic solvent, adding 2-pyridine-formaldehyde according to a certain substance amount ratio, and stirring for several hours at a certain temperature; it is also possible to use a solid phase reaction, i.e. a reaction of the two reactants by grinding, without using an organic solvent.
2) Filtering, and naturally volatilizing the filtrate to separate out yellow blocky crystals which are target products; if solid phase reaction is adopted, the target product crystal can be obtained by recrystallization with proper organic solvent after the reaction is finished.
The second method is characterized in that: taking (E) -2- (hydrazono) thiazole and 2-pyridine-formaldehyde as raw materials, and completing the steps in a proper organic solvent in one step, wherein the steps comprise:
1) dissolving 2-pyridine-formaldehyde in a proper organic solvent, adding (E) -2- (hydrazono) thiazole according to a certain substance amount ratio, and stirring for several hours at a certain temperature to obtain the compound preparation; it is also possible to use a solid phase reaction, i.e. a reaction of the two reactants by grinding, without using an organic solvent.
2) Filtering, and naturally volatilizing the filtrate to separate out yellow blocky crystals which are target products; if solid phase reaction is adopted, the target product crystal can be obtained by recrystallization with proper organic solvent after the reaction is finished.
The two above processes differ in the order of addition of the reactants, but the molar ratio of the reactants is between 1:4 and 4: 1.
The organic solvent (including the solvent for reaction or the solvent for recrystallization) in the above two methods is selected from: methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran, acetone, etc., and the reaction may be carried out without using an organic solvent, and the raw materials may be reacted directly (i.e., solid phase reaction).
Preferably, the reaction temperature is normal temperature or heating reflux, and the reaction method is stirring or grinding.
Preferably, the reaction time is selected from: 1-10 h.
The invention has the beneficial effects that: can synthesize more complex functional molecular materials by simpler steps and reactants.
3. Ultraviolet and fluorescent properties
The compound has three strong absorption peaks near 220.0nm, 260nm and 322.0nm, and the ultraviolet spectrum is shown in figure 4; has strong fluorescence emission peak in the range of 350.0-425.0nm, and the fluorescence spectrum is shown in figure 5; this indicates that the compound has better fluorescence properties.
4. In vitro antitumor activity:
respectively digesting A549 lung cancer cell, A375 human malignant melanoma cell and HeLa cervical cancer cell in logarithmic phase with 0.25% pancreatin to obtain single cells, and preparing into 1.25 × 10 concentration by using F12K culture solution containing 10% fetal calf serum 7 One cell/L suspension of single cells, cells were seeded in 96-well plates at 200. mu.L per well (2.5X 10 per well) 3 Individual cells). Place 96-well cell culture plates in CO 2 In an incubator at 37 ℃ with 5% CO 2 Culturing for 48h under the condition.
When the cells in the wells are full (90% full), adding different doses of the Schiff base solution (200 muL/well) according to experimental groups to make the final concentration of the compound to be detected respectively 12.5 muM, 25 muM, 50 muM, 100 muM, 200 muM and 400 muM, 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 cells were further cultured 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 calculated according to the following formula:
percent cell inhibition (control OD value-experimental OD value)/control OD value × 100%
Test results show that IC50 (half inhibition concentration of the drug) of the Schiff base on A549 lung cancer cells, A375 human malignant melanoma cells and HeLa cervical cancer cells is 495 mu mol/L, 453 mu mol/L and 403 mu mol/L respectively, and the Schiff base has weak inhibition effect on the three cancer cells.
Detailed Description
For better understanding of the present invention, the technical solution of the present invention is further illustrated by a specific example below:
example 1
0.1270g (about 1mmol) of (E) -2- (hydrazono) thiazole was dissolved in 50ml of acetonitrile, the solution was put into a flask, a magnetic stirrer heated at a constant temperature was placed and stirred, 0.2243g (about 2mmol) of 2-pyridine-formaldehyde was weighed into the solution, and the reaction was stirred under heating and reflux for 2 hours. The solution gradually turns to dark yellow, after the reaction is finished, the solution is filtered, and the filtrate is kept stand and naturally volatilized; the bottom of the beaker is separated out block-shaped yellow block-shaped crystals which are the target product, and the yield is about 87 percent.
Drawings
FIG. 1 is a 2- ((E) - (((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole 1 HNMR spectrogram (DMSO-D) 6 )。
FIG. 2 is a crystal structure diagram of 2- ((E) - ((((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 3 is a graphic stacking of the crystal structures of 2- ((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 4 is a UV spectrogram of 2- ((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
FIG. 5 is a fluorescence spectrum of 2- ((E) - (((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
Claims (3)
1. A compound having a yellow block appearance and a melting point of: 114.8-116.8 deg.C, molecular formula C 10 H 8 N 4 S, the chemical name is: 2- ((E) -pyridin-2-ylmethylene) hydrazono) methyl) thiazole, having the structure:
the substance crystal belongs to monoclinic system, and has space group P21/c, a =9.9633(18) A, b =9.0506(12) A and c =
β＝92.436(13)°，
Z＝4。
2. A method of synthesizing a compound as claimed in claim 1, characterized in that: the (E) -2- (hydrazono) thiazole and 2-pyridine-formaldehyde are used as raw materials, and liquid phase synthesis or solid phase synthesis can be adopted:
1) if a liquid phase synthesis method is adopted, completely dissolving (E) -2- (hydrazono) thiazole in a methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran or acetone organic solvent, adding 2-pyridine-formaldehyde according to the mass ratio of 1:4 to 4:1, stirring for 1-10 hours at normal temperature or at the reflux temperature, filtering, and naturally volatilizing the filtrate to precipitate yellow blocky crystals, namely the target product;
2) if the solid-phase synthesis method is adopted, the two reaction raw materials are mixed according to the mass ratio of 1:4 to 4:1, then grinding reaction is carried out for 1-10 h at normal temperature, and then methanol, ethanol, acetonitrile, dichloromethane, chloroform, tetrahydrofuran or acetone organic solvent is used for recrystallization, thus obtaining the target product crystal.
3. Use of a compound as claimed in claim 1, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for the treatment of tumours, wherein: the tumor is lung cancer, malignant melanoma or cervical cancer.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603619A (en) * | 2012-02-15 | 2012-07-25 | 合肥工业大学 | Compound with anticancer activity and preparation method thereof |
| CN110229119A (en) * | 2019-05-21 | 2019-09-13 | 辽宁科技大学 | A kind of synthesis and application method of the benzothiazole bis-Schiff base fluorescent molecular probe for iron ion detection |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603619A (en) * | 2012-02-15 | 2012-07-25 | 合肥工业大学 | Compound with anticancer activity and preparation method thereof |
| CN110229119A (en) * | 2019-05-21 | 2019-09-13 | 辽宁科技大学 | A kind of synthesis and application method of the benzothiazole bis-Schiff base fluorescent molecular probe for iron ion detection |
Non-Patent Citations (3)
| Title |
|---|
| "Ag(I) Complexes Generated from Double Schiff-Base Ligand with Thiazole as the Terminal Binding Sites";Yu-Bin Dong等;《CRYSTAL GROWTH & DESIGN》;20061231;第6卷(第11期);全文 * |
| "Synthesis and Biological Evaluation of Benzo[d]isothiazole，Benzothiazole and Thiazole Schiff Bases";Paola Vicini等;《Bioorganic & Medicinal Chemistry》;20031231(第11期);全文 * |
| "新型吲哚类席夫碱的合成、结构表征及抗癌活性研究";卜凡志;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20180415(第04期);全文 * |
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