CN107043345A - Preparation, structure and the purposes of the diketone Schiff base of 4-acetylbiphenyl hydrazone indoline 2,3 - Google Patents
Preparation, structure and the purposes of the diketone Schiff base of 4-acetylbiphenyl hydrazone indoline 2,3 Download PDFInfo
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- CN107043345A CN107043345A CN201710468260.5A CN201710468260A CN107043345A CN 107043345 A CN107043345 A CN 107043345A CN 201710468260 A CN201710468260 A CN 201710468260A CN 107043345 A CN107043345 A CN 107043345A
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- indoline
- diketone
- compound
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- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000002262 Schiff base Substances 0.000 title abstract description 14
- -1 diketone Schiff base Chemical class 0.000 title abstract description 3
- LWIKKBJFVMADMZ-UHFFFAOYSA-N N1CCC2=CC=CC=C12.C(C)(C1=CC=C(C=C1)C1=CC=CC=C1)=NN Chemical compound N1CCC2=CC=CC=C12.C(C)(C1=CC=C(C=C1)C1=CC=CC=C1)=NN LWIKKBJFVMADMZ-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 5
- 206010009944 Colon cancer Diseases 0.000 claims abstract description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 4
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 4
- 239000004305 biphenyl Substances 0.000 claims abstract description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims abstract description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 3
- 206010006187 Breast cancer Diseases 0.000 claims abstract 2
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- HDDXXLBVPQVLQK-UHFFFAOYSA-N 1-(4-phenylphenyl)ethylidenehydrazine Chemical compound C1=CC(C(=NN)C)=CC=C1C1=CC=CC=C1 HDDXXLBVPQVLQK-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012264 purified product Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 abstract description 3
- 201000005296 lung carcinoma Diseases 0.000 abstract description 3
- 239000002585 base Substances 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FJXPRESVZTVXCF-BUVRLJJBSA-N C/C(/c(cc1)ccc1-c1ccccc1)=N\N=C(/c(cccc1)c1N1)\C1=O Chemical compound C/C(/c(cc1)ccc1-c1ccccc1)=N\N=C(/c(cccc1)c1N1)\C1=O FJXPRESVZTVXCF-BUVRLJJBSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000006948 antiviral bioactivity Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 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 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003746 solid phase reaction 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
- 238000001308 synthesis method Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
The present invention relates to a kind of structure, preparation method and some properties of Schiff base compound.The compound outward appearance is in yellow powdery solid, 235.8 236.3 DEG C of fusing point, molecular formula C22H17N3O, chemistry is entitled：(E) ketone of 3 ((E) (1 (base of biphenyl 4) ethylidene) hydrazine fork) indoline 2, structure is as follows：The compounds process for production thereof is simple, to A549 lung carcinoma cells, 4T1The IC50 (half-inhibition concentration of medicine) of breast cancer cell and the colon cancer cells of CT 26 is respectively 40.5 μM, 47.0 μM and 38.5 μM, and this shows that the compound has certain inhibition to these three cancer cells.
Description
Technical field
The present invention relates to organic synthesis and medicinal chemistry art, better simply raw material and method one-step synthesis target have been used
Product.
Background technology
Schiff base is a kind of more special compound of structure, can synthesize different types of according to the difference for introducing group
Schiff base.Schiff base has important application in medical science, catalysis, analytical chemistry, corrosion and the field such as photochromic.For example,
Medical domain, Schiff base has antibacterial, sterilization, antitumor, antiviral bioactivity；In optical material field, because it is rich
The characteristics of electronics and rigid plane, make it have good fluorescence property and nonlinear optical property.
The report that 4-acetylbiphenyl hydrazone class Schiff base is used for medicine is less, but the drug molecule of the ring structure containing biphenyl is very normal
See；In drug design field, the cyclohexyl biphenyl stable system fragrant hydrophobic interaction of drug molecule, therefore it is commonly used for medicine
The structure of molecule.
The content of the invention
Present disclosure is to have synthesized a kind of 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base compound, the chemical combination
It is in yellow powdery solid, 235.8-236.3 DEG C of fusing point, molecular formula C that beyond the region of objective existence, which is seen,22H17N3O, chemistry is entitled：(E)-3-((E)-
(1- (biphenyl -4- bases) ethylidene)-hydrazine is pitched) indole-2-ketone, [english system is named as：(E)-3-((E)-(1-
(biphenyl-4-yl) ethylidene) hydrazono) indolin-2-one], it is abbreviated as 3-BEHIO；Structure is as follows.
1st, Structural Identification.
Elementary analysis shows, its C, H, N percentage composition is respectively 77.91%, 5.11% and 12.42% (to be based on molecule
Formula C22H17N3O theoretical value is respectively 77.86%, 5.05% and 12.38%), relevant1HNMR spectrums are shown in accompanying drawing 1.
2nd, synthetic method.
It is characterised by the compound synthesis method：With 4-acetylbiphenyl hydrazone and indoline -2,3- diketone for raw material, use
Solution is synthesized or solid-phase synthesis.Step is as follows：
1) 4-acetylbiphenyl hydrazone and indoline -2,3- diketone are dissolved in suitable organic solvent respectively, then by certain
Mixed in molar ratio, at a certain temperature stirring reaction certain time；Two kinds of reactions can also be directly mixed without organic solvent
Thing, griding reaction.
2) during liquid phase reactor, obtained solution is removed into most of solvent using certain method, yellow powder is can obtain
Shape solid, as target product；During solid phase reaction, grinding certain time can obtain target product.
3) target product can be recrystallized with purified product in suitable organic solvent.
It is preferred that, above-mentioned reaction dissolvent or recrystallization are selected from organic solvent：Methanol, ethyl acetate, dichloromethane, second
Alcohol, acetonitrile, acetone, chloroform, tetrahydrofuran.
It is preferred that, the reaction mol ratio of 4-acetylbiphenyl hydrazone and indoline -2,3- diketone is 1:4 to 4:1.
It is preferred that, the reaction temperature is room temperature to being heated to reflux.
It is preferred that, the reaction time is：0.5-12 hours.
It is preferred that, the method for removing solvent is volatilized or often/vacuum distillation for nature.
The beneficial effects of the invention are as follows：Can be with fairly simple step and the more complicated function of reactant one-step synthesis
Molecular material, and separation method is simple.
3rd, anti tumor activity in vitro：
The A549 lung carcinoma cells that will be grown in logarithmic phase, 4T1Breast cancer cell and CT-26 colon cancer cells, are used respectively
0.25% trypsin digestion cell, becomes unicellular, and concentration is made of the F12K nutrient solutions containing 10% hyclone for 1.25
×107Individual/L single cell suspension, cell is inoculated in 96 well culture plates, per the μ L of hole 200 (per hole 2.5 × 103Individual cell).
96 porocyte culture plates are placed in CO2In incubator, in 37 DEG C, 5%CO2Under the conditions of, cultivate 48h.
When hole, inner cell covers with (90% is full), empirically packet adds this Schiff base solution (200 of various dose
μ L/ holes), the final concentration for making testing compound is respectively 5 μM, 10 μM, 30 μM, 50 μM, 100 μM, and every group sets 3 multiple holes, culture
96h。
The MTT that 20 μ L concentration are 0.5g/L is separately added into each hole, continues to cultivate 4h, MTT is reduced to first a ceremonial jade-ladle, used in libation
(Formazan).Suction out after whole supernatants, 200 μ L DMSO is added per hole, 15min is shaked, make after first a ceremonial jade-ladle, used in libation fully dissolves, fortune
The absorbance (OD values) at 490nm is determined with enzyme-linked immunosorbent assay instrument.Then calculated according to the following formula：
Cell inhibitory rate %=(control group OD values-experimental group OD values)/control group OD value × 100%
Test result shows that the Schiff base is to A549 lung carcinoma cells, 4T1Breast cancer cell and CT-26 colon cancer cells
IC50 (half-inhibition concentration of medicine) is respectively 40.5 μM, 47.0 μM and 38.5 μM, and this shows the compound to these three cancers
Cell has certain inhibition.
Embodiment
In order to be better understood from present invention, the technology of the present invention is further illustrated below by two specific embodiments
Scheme：
Embodiment 1.
4-acetylbiphenyl hydrazone 0.20g (0.95mmol) is weighed to be dissolved in 30mL absolute methanols, heating stirring to whole dissolvings, plus
Enter indoline -2,3- diketone 0.14g (0.95mmol), be heated to reflux stirring 6 hours, be then filtrated to get filtrate, be placed in beaker
It is middle to stand volatilization, largely powdered precipitation can be obtained, head product (yield is about 79%), this head product will be obtained after gained precipitation filtering
Ethyl alcohol recrystallization can be used, yellow powdery solid, as 3-BEHIO Schiff bases is obtained.
Embodiment 2.
Weigh 4-acetylbiphenyl hydrazone 0.40g (1.9mmol) to be put into mortar, add indoline -2,3- diketone 0.28g
(1.9mmol), grinds 3 hours, obtains target product crude product；By gained powder ethyl alcohol recrystallization, yellow powdery solid is obtained,
As 3-BEHIO Schiff bases.
Brief description of the drawings
Accompanying drawing 1 is 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff bases1H NMR spectras.
Claims (4)
1. a kind of compound, outward appearance is in yellow powdery solid, 235.8-236.3 DEG C of fusing point, molecular formula C22H17N3O, chemical name
For：(E) -3- ((E)-(1- (biphenyl -4- bases) ethylidene)-hydrazine fork) indole-2-ketone, structure is as follows.
2. the preparation method of compound as described in the appended claim 1, it is characterised in that：With 4-acetylbiphenyl hydrazone and indoline -2,3-
Diketone is raw material, and using solution synthetic method, step is as follows：
1) by 4-acetylbiphenyl hydrazone and indoline -2,3- diketone be dissolved in respectively methanol, ethyl acetate, dichloromethane, ethanol, acetonitrile,
In acetone, chloroform or tetrahydrofuran organic solvent, then by 1:4 to 4:1 mixed in molar ratio, in room temperature at a temperature of being heated to reflux
Stirring reaction 0.5-12 hours；
2) obtained solution is volatilized using nature or often/vacuum distillation method removes most of solvent, can obtain yellow powder,
As target product；
3) target product can be organic in methanol, ethyl acetate, dichloromethane, ethanol, acetonitrile, acetone, chloroform or tetrahydrofuran
Recrystallized in solvent with purified product.
3. the preparation method of compound as described in the appended claim 1, it is characterised in that：With 4-acetylbiphenyl hydrazone and indoline -2,3-
Diketone is raw material, and using solid-phase synthesis, step is as follows：
1) 4-acetylbiphenyl hydrazone and indoline -2,3- diketone are pressed 1:4 to 4:1 mixed in molar ratio, at room temperature griding reaction 0.5-
12 hours, gained powder was target product head product；
2) target product head product can be in methanol, ethyl acetate, dichloromethane, ethanol, acetonitrile, acetone, chloroform or tetrahydrochysene furan
Mutter and recrystallize with purified product in organic solvent.
4. as described in the appended claim 1 compound or its pharmaceutically acceptable salt prepare prevention and/or treatment tumour medicine
Application in thing, it is characterised in that：The tumour is lung cancer, breast cancer or colon cancer.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710468260.5A CN107043345B (en) | 2017-06-20 | 2017-06-20 | 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base preparation, structure and purposes |
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| CN201710468260.5A CN107043345B (en) | 2017-06-20 | 2017-06-20 | 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base preparation, structure and purposes |
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| CN107043345A true CN107043345A (en) | 2017-08-15 |
| CN107043345B CN107043345B (en) | 2019-07-05 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824572A (en) * | 2019-04-08 | 2019-05-31 | 齐鲁工业大学 | Structure, the preparation and use of -3 indolecarboxaldehyde schiff bases of 4- dihydroxy benaophenonel hydrazone -1- methyl |
| CN109912517A (en) * | 2019-04-08 | 2019-06-21 | 齐鲁工业大学 | The preparation and use of 4- dihydroxy benaophenonel hydrazone -2- acetyl group pyrazine schiff bases |
| CN109912491A (en) * | 2019-04-08 | 2019-06-21 | 齐鲁工业大学 | 4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use |
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| 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 |
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| US6075044A (en) * | 1997-07-21 | 2000-06-13 | The Regents Of The University Of California | Heterocyclic derivatives as inhibitors of purine salvage phosphoribosyltransferases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109824572A (en) * | 2019-04-08 | 2019-05-31 | 齐鲁工业大学 | Structure, the preparation and use of -3 indolecarboxaldehyde schiff bases of 4- dihydroxy benaophenonel hydrazone -1- methyl |
| CN109912517A (en) * | 2019-04-08 | 2019-06-21 | 齐鲁工业大学 | The preparation and use of 4- dihydroxy benaophenonel hydrazone -2- acetyl group pyrazine schiff bases |
| CN109912491A (en) * | 2019-04-08 | 2019-06-21 | 齐鲁工业大学 | 4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use |
| CN109912517B (en) * | 2019-04-08 | 2020-08-07 | 齐鲁工业大学 | Preparation and application of 4-hydroxybenzophenone hydrazone-2-acetylpyrazine Schiff base |
| CN109912491B (en) * | 2019-04-08 | 2020-08-07 | 齐鲁工业大学 | Preparation and application of 4-hydroxybenzophenone hydrazone-isatin Schiff base |
| CN109824572B (en) * | 2019-04-08 | 2020-08-07 | 齐鲁工业大学 | Structure, preparation and application of 4-hydroxybenzophenone hydrazone-1-methyl-3 indole formaldehyde Schiff base |
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| CN107043345B (en) | 2019-07-05 |
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