CN110590763B - Structure, preparation and application of 2-thiazole formaldehyde-thiophene Schiff base - Google Patents
Structure, preparation and application of 2-thiazole formaldehyde-thiophene Schiff base Download PDFInfo
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- CN110590763B CN110590763B CN201910941334.1A CN201910941334A CN110590763B CN 110590763 B CN110590763 B CN 110590763B CN 201910941334 A CN201910941334 A CN 201910941334A CN 110590763 B CN110590763 B CN 110590763B
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- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000002262 Schiff base Substances 0.000 title description 11
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- KBKWSDMWJONSRZ-GNXRPPCSSA-N S1C(=CC=C1)\C=N\N=C\C=1SC=CN=1 Chemical compound S1C(=CC=C1)\C=N\N=C\C=1SC=CN=1 KBKWSDMWJONSRZ-GNXRPPCSSA-N 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
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- 238000001914 filtration Methods 0.000 claims description 4
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- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 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
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 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
- 239000007791 liquid phase Substances 0.000 claims 2
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
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- 150000003839 salts Chemical class 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000036961 partial effect Effects 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 7
- 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
- 239000000376 reactant Substances 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
- 238000003746 solid phase reaction Methods 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
- -1 Schiff base compounds Chemical class 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
- 229940079593 drug Drugs 0.000 description 2
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- 238000005516 engineering process 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
- 238000002211 ultraviolet spectrum Methods 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
- 239000006285 cell suspension Substances 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
- 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
- 238000010189 synthetic method Methods 0.000 description 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
The invention relates to a structure, a preparation method and partial properties of a compound crystal. The compound is brown needle crystal in appearance, has a melting point of 118.1-122.2 deg.C, and has a molecular formula of C 9 H 7 N 3 S 2 The chemical name is: 2- ((E) - (((E) -thiophen-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 properties of the fluorescence are also more and more deeply researched. Fluorescent substances have been widely used in the fields of dyes, organic pigments, optical brighteners, photo-oxidizers, coatings, chemical and biochemical marking analysis, solar collectors, anti-counterfeiting marks, drug tracing, lasers and the like. The organic fluorescent material is mainly used in the current popular technologies, 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; in the field of photochromism, certain schiff bases containing characteristic groups also have unique applications.
Disclosure of Invention
The invention relates to a compound which can be used as fluorescent material and anticancer drug, wherein the compound is brown needle crystal in appearance, and the melting point is as follows: 118.1-122.2 deg.C, and molecular formula C 9 H 7 N 3 S 2 The chemical name is: 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole, having the structure:
1. and (3) structure identification:
elemental analysis showed that this compound has the formula C 9 H 7 N 3 S 2 Molecular weight 221.30; elemental analysis results (%): the experimental values of C,48.82, H,3.16, N,18.88, S, 28.95; calculated values: c,48.85, H,3.19, N,18.89, S, 28.97; the analysis of the single crystal structure shows that the substance crystal belongs to a monoclinic system, the space group is P21/c,
β＝102.459(10)°，
z is 4; in connection with 1 HNMR spectra are 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 I is characterized in that: taking (E) -2- (hydrazono) thiazole and thiophene-2-formaldehyde as raw materials, and completing the preparation in one step in a proper organic solvent. The method comprises the following steps:
1) dissolving (E) -2- (hydrazono) thiazole in a proper organic solvent, adding thiophene-2-formaldehyde according to a certain substance quantity ratio, and stirring or grinding at a certain temperature for reacting for several hours.
2) Filtering, and naturally volatilizing the filtrate to precipitate brown needle crystals which are target products; if solid phase reaction is adopted, the target product crystal can be obtained by recrystallization with a proper organic solvent after the reaction is finished.
The second method is characterized in that: taking (E) -2- (hydrazono) thiazole and thiophene-2-formaldehyde as raw materials, and completing the steps in a proper organic solvent in one step, wherein the steps are as follows:
1) dissolving thiophene-2-formaldehyde in a proper organic solvent, adding (E) -2- (hydrazono) thiazole according to a certain substance amount ratio, and stirring or grinding to react for several hours at a certain temperature.
2) Filtering, and naturally volatilizing the filtrate to separate out brown needle 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 4:1 and 1: 4.
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 directly reacted with each other (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 at 236.0nm, 266nm and 345.0nm, and the ultraviolet spectrum is shown in figure 4; has strong fluorescence emission peak in 375.0-450.0nm range, 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 Single cell suspension per L, 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 129, 390 and 353 mu mol/L respectively, and the compound has weak inhibition effects 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
0.12701g (ca. 1mmol) of (E) -2- (hydrazono) thiazole were weighed out and dissolved in 50ml of acetonitrile, the solution was placed in a flask, stirred on a constant temperature heating magnetic stirrer, 187. mu.L (ca. 2mmol) was added to the solution by sucking with a pipette, and the reaction was stirred under reflux for 2 hours. Gradually changing the solution into yellow brown, filtering after the reaction is finished, standing the filtrate, and naturally volatilizing; brown needle-shaped crystals are separated out from the bottom of the beaker, namely the target product, and the yield is about 84 percent.
Drawings
FIG. 1 is a 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole 1 HNMR spectrogram (DMSO-D) 6 )。
FIG. 2 is a crystal structure diagram of 2- ((E) - ((((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 3 is a graphic representation of the crystal structure of 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole.
FIG. 4 is a UV spectrum of 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
FIG. 5 is a fluorescence spectrum of 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole (10) - 5 mol/L,CH 2 CL 2 )。
Claims (3)
1. A compound which is brown needle-like in appearance and has a melting point of: 118.1-122.2 deg.C, and molecular formula C 9 H 7 N 3 S 2 (ii) a The chemical name is: 2- ((E) - (((E) -thiophen-2-ylmethylene) hydrazono) methyl) thiazole, having the structure:
the material crystal belongs to a monoclinic system, the space group is P21/c,
β＝102.459(10)°，
Z＝4。
2. a method of synthesizing a compound as claimed in claim 1, characterized in that: the (E) -2- (hydrazono) thiazole and the thiophene-2-formaldehyde are taken 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 thiophene-2-formaldehyde according to the amount ratio of 1:4 to 4:1, stirring for 1-10 hours at normal temperature or at the reflux temperature, filtering, and after the filtrate is naturally volatilized, separating out brown needle-shaped crystals which are target products;
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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|---|---|---|---|---|
| JP4744144B2 (en) * | 2002-08-30 | 2011-08-10 | 株式会社ブリヂストン | Functional polymers and vulcanizates improved thereby |
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