CN109912491A - 4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use - Google Patents
4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use Download PDFInfo
- Publication number
- CN109912491A CN109912491A CN201910274629.8A CN201910274629A CN109912491A CN 109912491 A CN109912491 A CN 109912491A CN 201910274629 A CN201910274629 A CN 201910274629A CN 109912491 A CN109912491 A CN 109912491A
- Authority
- CN
- China
- Prior art keywords
- compound
- organic solvent
- follows
- hydrazone
- isatin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
The present invention relates to a kind of structure of compound crystal, preparation method and some properties.This compound appearance be in orange bulk crystals, 240.9-244.3 DEG C of fusing point, molecular formula C21H15N3O2, chemical name are as follows: E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone；The compound structure is detailed in specification, has certain photoluminescent property and anticancer activity.
Description
Technical field
The present invention relates to the fields such as organic synthesis, optical material and pharmaceutical chemistry, use simpler method one-step synthesis
Target product the advantage is that novelty, simple and easy synthetic method, higher purity and the yield of compound structure.
Background technique
Currently, being constantly progressive with modern science and technology, people are more and more to the research of fluorescence, to its photoluminescent property
Research it is also more and more deep.Fluorescent material is in dyestuff, organic pigment, Optical Bleaching Agent, photooxidant, coating, chemistry and life
Change the fields such as labeled analysis, solar energy trap, anti-fake mark, pharmaceutical indications and laser to have obtained more being widely applied.Its
Middle organic fluorescence materials are mainly used for the technology of current hot topic, such as fluorescence probe, fluorescence analysis, even more optical electron device,
The indispensable material of DNA diagnosis, Optochemical sensor, laser dye, organic electroluminescence device.
Schiff bases is primarily referred to as a kind of organic compound containing imines or azomethine characteristic group (- RC=N-), usually
Schiff bases is condensed by amine and active carbonyl group.Schiff bases compound and its metal complex mainly medicine and pharmacology, catalysis,
There is important application in analytical chemistry, corrosion and photochromic field.In medical domain, schiff bases has antibacterial, sterilization, resists and swell
Tumor, antiviral bioactivity；In catalytic field, the complex of the cobalt of schiff bases, nickel and palladium has been used as catalyst to use；?
Analytical chemistry field, schiff bases can be used to identify, identify metal ion and quantitative analysis metal ion as good ligand
Content；In corrosion field, certain aromatic schiff bases pass through the corrosion inhibiter frequently as copper；In photochromic field, it is certain containing
The schiff bases of characteristic group also has unique application.
Summary of the invention
The contents of the present invention are to synthesize a kind of compound that can be used as fluorescent material and anticancer drug, and compound appearance is in
Orange bulk, fusing point are as follows: 240.9-244.3 DEG C, molecular formula C21H15N3O2, chemical name are as follows: E-3- ((Z- (4- hydroxy phenyl) (benzene
Base) methylene) hydrazono-) indole-2-ketone, structure is as follows:
1, Structural Identification:
Elemental analysis shows that the molecular formula that this compound has is C21H15N3O2；Single crystal structure analysis shows that its crystallization belongs to
Monoclinic system, space group are P 21/c, β=
102.685 (4) °,Z=8；It is related1HNMR spectrum is shown in that attached drawing 1, attached drawing 2, attached drawing 3 are the compound respectively
Hot ellipsoid crystal structure figure and crystal structure accumulation graph.
2, synthetic method.
Synthetic method is characterized in that: using 4- dihydroxy benaophenonel hydrazone and isatin as raw material, in suitable organic solvent
One step is completed.Steps are as follows:
1) after 4- dihydroxy benaophenonel hydrazone being all dissolved in suitable organic solvent, add according to certain the ratio between amount of substance
Enter isatin, stirring or griding reaction a few houres can be completed at a certain temperature.
2) it filters, volatilizees naturally to filtrate, the orange bulk crystals of precipitation are target product；According to solid phase reaction,
Then end of reaction is recrystallized with suitable organic solvent can obtain target product crystal.
Method two is characterized in that: using 4- dihydroxy benaophenonel hydrazone and isatin as raw material, one in suitable organic solvent
Step is completed, and steps are as follows:
1) after isatin being all dissolved in suitable organic solvent, 4- hydroxyl hexichol is added according to the ratio between certain amount of substance
Ketone hydrazone, stirring or griding reaction a few houres can be completed at a certain temperature.
2) it filters, volatilizees naturally to filtrate, the orange bulk crystals of precipitation are target product；According to solid phase reaction,
Then end of reaction is recrystallized with suitable organic solvent can obtain target product crystal.
The difference of both the above method is that reactant charging sequence is different, but the molar ratio of reactant between 2:1 with
Between 1:3.
Organic solvent (anti-solvent-applied or recrystallization solvent) in both the above method is selected from: methanol, ethyl alcohol, second
Nitrile, methylene chloride, chloroform, tetrahydrofuran, acetone etc., can also not have to organic solvent when reaction, between raw material directly reaction (Gu
Phase reaction).
Preferably, the reaction temperature is room temperature or is heated to reflux, and reaction method is stirring or grinding.
Preferably, the reaction time is selected from: 2-10h.
The beneficial effects of the present invention are: more complicated functional molecular can be synthesized with fairly simple step and reactant
Material.
3, ultraviolet and photoluminescent property
For compound there are two strong absworption peak near 207.0nm and 250.0nm, ultraviolet spectra is shown in attached drawing 4；In 370.0-
460.0nm range has very strong fluorescence emission peak, and fluorescence spectrum is shown in attached drawing 5；This shows that the compound has preferable photoluminescent property.
4, anti tumor activity in vitro:
By the A549 lung carcinoma cell in logarithmic phase growth, 4T1Breast cancer cell and Hep G2 liver cancer cells, are used respectively
0.25% trypsin digestion cell, become it is unicellular, with containing 10% fetal calf serum F12K culture solution be made concentration be 1.25
×107The single cell suspension of a/L, by cell inoculation in 96 well culture plates, (the every hole 2.5 × 10 every 200 μ L of hole3A cell).
96 porocyte culture plates are placed in CO2In incubator, at 37 DEG C, 5%CO2Under the conditions of, cultivate 48h.
When inner cell covers with (90% is full) when hole, this Schiff aqueous slkali (200 of various dose is added by experimental group
The hole μ L/), making the final concentration of untested compound is respectively 5 μM, 10 μM, 30 μM, 50 μM, 100 μM, and every group sets 3 multiple holes, culture
96h。
It is separately added into the MTT that 20 μ L concentration are 0.5g/L in each hole, continues to cultivate 4h, MTT is made to be reduced to first a ceremonial jade-ladle, used in libation
(Formazan).After whole supernatants are sucked out, the DMSO of 200 μ L is added in every hole, is shaked 15min, is made first a ceremonial jade-ladle, used in libation after completely dissolution, is transported
With the absorbance (OD value) at enzyme-linked immunosorbent assay instrument measurement 490nm.Then it is calculated according to the following formula:
Cell inhibitory rate %=(control group OD value-experimental group OD value)/control group OD value × 100%
Test result shows the schiff bases to A549 lung carcinoma cell, 4T1Breast cancer cell and Hep G2 liver cancer cells
IC50 (half-inhibitory concentration of drug) is respectively 81.0 μM, 92.0 μM and 103.0 μM, this shows the compound to these three cancers
Cell has certain inhibitory effect.
Specific embodiment
Content in order to better understand the present invention further illustrates technology of the invention below by a specific embodiment
Scheme:
Embodiment 1
It weighs 0.1995g (about 0.94mmol) 4- dihydroxy benaophenonel hydrazone to be dissolved in 50ml acetonitrile, solution is put into flask
It is interior, it is placed on constant-temperature heating magnetic stirring apparatus and stirs, weigh 0.1384g (about 0.94mmol) isatin and be added in solution, heat back
Stream is stirred to react 2 hours.Solution gradually becomes buff, and after reaction, filtering, filtrate stands, and volatilizees naturally；Beaker bottom
Blocky orange crystal, as target product is precipitated.
Detailed description of the invention
Attached drawing 1 is E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone1HNMR spectrum
Figure.
Attached drawing 2 is the crystal structure of E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone
Figure.
Attached drawing 3 is the crystal structure of E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone
Accumulation graph.
Attached drawing 4 is the ultraviolet spectra of E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone
Figure.
Attached drawing 5 is the fluorescence spectrum of E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone
Figure.
Claims (5)
1. a kind of compound, appearance is in orange bulk crystals, fusing point are as follows: 240.9-244.3 DEG C, molecular formula C21H15N3O2, chemistry
Name are as follows: E-3- ((Z- (4- hydroxy phenyl) (phenyl) methylene) hydrazono-) indole-2-ketone, structure are as follows:
It, which is crystallized, belongs to monoclinic system, space group P21/c, β=102.685 (4) °,Z=8.
2. the synthetic method of compound as described in claim 1, it is characterised in that: with 4- dihydroxy benaophenonel hydrazone and isatin
For raw material, reacted in methanol, ethyl alcohol, acetonitrile, methylene chloride, chloroform, tetrahydrofuran, acetone and other organic solvent, steps are as follows:
1) after 4- dihydroxy benaophenonel hydrazone being all dissolved in organic solvent, isatin is added by the ratio between 2:1 to the amount of 1:3 substance,
Stirring or griding reaction 2-10h can be completed under certain temperature；According to solid phase reaction, then organic solvent can not be had to；
2) it filters, volatilizees naturally to filtrate, the orange bulk crystals of precipitation are target product；According to solid phase reaction, then may be used
With methanol, ethyl alcohol, acetonitrile, methylene chloride, chloroform, tetrahydrofuran, acetone and other organic solvent recrystallization, target product crystalline substance can be obtained
Body.
3. the synthetic method of compound as stated in claim 2, it is characterised in that: reaction temperature is room temperature or is heated to back
Stream.
4. compound crystal as described in claim 1 is in dyestuff, organic pigment, Optical Bleaching Agent, photooxidant, coating, chemistry
And biochemical marker analysis, solar energy trap, anti-fake mark, pharmaceutical indications, fluorescence probe, fluorescence analysis, optical electron device,
The purposes in the fields such as Optochemical sensor, laser dye, organic electroluminescence device, the purposes are based on its photoluminescent property.
5. as described in the appended claim 1 in compound crystal or other pharmacology acceptable salt in preparation tumor
Application, it is characterised in that: the tumour be lung cancer, breast cancer or liver cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910274629.8A CN109912491B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of 4-hydroxybenzophenone hydrazone-isatin Schiff base |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910274629.8A CN109912491B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of 4-hydroxybenzophenone hydrazone-isatin Schiff base |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109912491A true CN109912491A (en) | 2019-06-21 |
| CN109912491B CN109912491B (en) | 2020-08-07 |
Family
ID=66968851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910274629.8A Active CN109912491B (en) | 2019-04-08 | 2019-04-08 | Preparation and application of 4-hydroxybenzophenone hydrazone-isatin Schiff base |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109912491B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115304536A (en) * | 2022-07-26 | 2022-11-08 | 合肥工业大学 | Preparation and application of indoline-2-ketone compound derivative |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945302A (en) * | 2015-06-12 | 2015-09-30 | 齐鲁工业大学 | Structure, preparation and application of benzil dihydrazone-indole-3-carboxaldehyde dual-Schiff base |
| CN107043345A (en) * | 2017-06-20 | 2017-08-15 | 齐鲁工业大学 | Preparation, structure and the purposes of the diketone Schiff base of 4-acetylbiphenyl hydrazone indoline 2,3 |
| CN107266348A (en) * | 2017-06-20 | 2017-10-20 | 齐鲁工业大学 | Preparation, structure and the purposes of the indolecarboxaldehyde Schiff base of 4-acetylbiphenyl hydrazone 3 |
-
2019
- 2019-04-08 CN CN201910274629.8A patent/CN109912491B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945302A (en) * | 2015-06-12 | 2015-09-30 | 齐鲁工业大学 | Structure, preparation and application of benzil dihydrazone-indole-3-carboxaldehyde dual-Schiff base |
| CN107043345A (en) * | 2017-06-20 | 2017-08-15 | 齐鲁工业大学 | Preparation, structure and the purposes of the diketone Schiff base of 4-acetylbiphenyl hydrazone indoline 2,3 |
| CN107266348A (en) * | 2017-06-20 | 2017-10-20 | 齐鲁工业大学 | Preparation, structure and the purposes of the indolecarboxaldehyde Schiff base of 4-acetylbiphenyl hydrazone 3 |
Non-Patent Citations (2)
| Title |
|---|
| ARSHIA等: "Synthesis and urease inhibitory potential of benzophenone sulfonamide hybrid in vitro and in silico", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| D.A.LEMENOVSKII等: "Nes metallocene complexes of Nb and Ta with functionalized", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115304536A (en) * | 2022-07-26 | 2022-11-08 | 合肥工业大学 | Preparation and application of indoline-2-ketone compound derivative |
| CN115304536B (en) * | 2022-07-26 | 2023-09-22 | 合肥工业大学 | Preparation and application of indoline-2-one compound derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109912491B (en) | 2020-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104945302A (en) | Structure, preparation and application of benzil dihydrazone-indole-3-carboxaldehyde dual-Schiff base | |
| CN107266348B (en) | Preparation, structure and the purposes of 4-acetylbiphenyl hydrazone -3- indolecarboxaldehyde Schiff base | |
| CN107043345B (en) | 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base preparation, structure and purposes | |
| CN110606843B (en) | Structure, preparation and application of bipyridyl ketone hydrazone-2-acetylpyrazine | |
| CN109912491A (en) | 4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use | |
| CN109824572A (en) | Structure, the preparation and use of -3 indolecarboxaldehyde schiff bases of 4- dihydroxy benaophenonel hydrazone -1- methyl | |
| CN107501303B (en) | Copper (II) complex and its synthetic method and application that a kind of brufen and quinoline-8-formaldehyde schiff bases are constructed | |
| CN109824647A (en) | The preparation and use of 4- dihydroxy benaophenonel hydrazone -2- acetyl thiophene schiff bases | |
| CN110790695A (en) | Synthesis and application of benzil hydrazone-N-methyl-3-indole formaldehyde | |
| CN107266349B (en) | Preparation, structure and the purposes of 4-acetylbiphenyl hydrazone -2- indolecarboxaldehyde Schiff base | |
| CN110590765B (en) | Structure, preparation and application of 2-thiazole formaldehyde-furfural Schiff base | |
| CN109912517A (en) | The preparation and use of 4- dihydroxy benaophenonel hydrazone -2- acetyl group pyrazine schiff bases | |
| CN106565755B (en) | Using 1- pyridine -6- methoxy-p-carbolines as copper nitrate (II) chelate and its synthetic method of ligand and application | |
| CN109912451A (en) | 4- dihydroxy benaophenonel hydrazone-schiff base of salicylaldehyde preparation and use | |
| CN105348146B (en) | Structure, preparation and use of benzil hydrazone-chlorobenzaldehyde bis-Schiff base | |
| CN110698383B (en) | Structure, synthesis and application of benzil hydrazone-3-acetyl indole | |
| CN109824541A (en) | The preparation and use of bis- ((2- fluorophenyl) (4- fluorophenyl) methylene) hydrazines of (1Z, 2Z) -1,2- | |
| CN110577521B (en) | Structure, preparation and application of 2-thiazole formaldehyde-2-pyridine Schiff base | |
| CN110590764B (en) | Structure, preparation and application of 2-thiazole formaldehyde-4-pyridine Schiff base | |
| CN107118147B (en) | Preparation, structure and the purposes of 4-acetylbiphenyl hydrazone -3- acetylindole Schiff base | |
| CN110590763B (en) | Structure, preparation and application of 2-thiazole formaldehyde-thiophene Schiff base | |
| CN110563667B (en) | Structure, preparation and application of 2-thiazole formaldehyde-1-naphthalene Schiff base | |
| CN110563716B (en) | Structure, preparation and application of 2-thiazole formaldehyde-6-indole Schiff base | |
| CN110590696B (en) | Structure, preparation and application of 2-thiazole formaldehyde Schiff base | |
| CN107043344B (en) | Preparation, structure and the purposes of 4-acetylbiphenyl hydrazone-N- methyl -3- indolecarboxaldehyde Schiff base |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20201224 Address after: 233000 No.10, building 32, Zone 8, Guangcai market, bengshan District, Bengbu City, Anhui Province Patentee after: Bengbu Hongjing Technology Co.,Ltd. Address before: 250353 Qilu University of technology, Changqing University Town, Jinan City, Shandong Province Patentee before: Qilu University of Technology |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220615 Address after: 401220 huangjueyan, Fengcheng street, Changshou District, Chongqing Patentee after: CHONGQING CHANGFENG CHEMICAL INDUSTRY Co.,Ltd. Address before: 233000 No.10, building 32, Zone 8, Guangcai market, bengshan District, Bengbu City, Anhui Province Patentee before: Bengbu Hongjing Technology Co.,Ltd. |
|
| TR01 | Transfer of patent right |