CN107043345B - 4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base preparation, structure and purposes - Google Patents
4-acetylbiphenyl hydrazone-indoline -2,3- diketone Schiff base preparation, structure and purposes Download PDFInfo
- Publication number
- CN107043345B CN107043345B CN201710468260.5A CN201710468260A CN107043345B CN 107043345 B CN107043345 B CN 107043345B CN 201710468260 A CN201710468260 A CN 201710468260A CN 107043345 B CN107043345 B CN 107043345B
- Authority
- CN
- China
- Prior art keywords
- indoline
- diketone
- compound
- follows
- target product
- 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.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000002262 Schiff base Substances 0.000 title abstract description 14
- 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
- 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 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- 206010009944 Colon cancer Diseases 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
- 239000000126 substance Substances 0.000 claims abstract description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 206010006187 Breast cancer Diseases 0.000 claims abstract 2
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 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
- 229940079593 drug Drugs 0.000 abstract description 6
- -1 Schiff base compound Chemical class 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 201000005296 lung carcinoma Diseases 0.000 abstract description 3
- 239000002585 base Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 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
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000003756 stirring 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
- 108091003079 Bovine Serum Albumin Proteins 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
- 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 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
- 238000011081 inoculation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 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
- 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
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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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 |
Applications Claiming Priority (1)
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 |
Publications (2)
Publication Number | Publication Date |
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CN107043345A CN107043345A (en) | 2017-08-15 |
CN107043345B true CN107043345B (en) | 2019-07-05 |
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CN201710468260.5A Expired - Fee Related 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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CN (1) | CN107043345B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
CN109912491B (en) * | 2019-04-08 | 2020-08-07 | 齐鲁工业大学 | Preparation and application of 4-hydroxybenzophenone hydrazone-isatin Schiff base |
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 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6075044A (en) * | 1997-07-21 | 2000-06-13 | The Regents Of The University Of California | Heterocyclic derivatives as inhibitors of purine salvage phosphoribosyltransferases |
WO2008009935A1 (en) * | 2006-07-19 | 2008-01-24 | Ucl Business Plc | Pharmaceutical compositions and their use |
CN104193650A (en) * | 2014-08-12 | 2014-12-10 | 齐鲁工业大学 | Structure, preparation and application of benzildihydrazone-N,N'-bis(1-formacylnaphthalene) |
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 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1725227A1 (en) * | 2004-03-03 | 2006-11-29 | Biolipox AB | Use of new lipoxygenase inhibitors |
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2017
- 2017-06-20 CN CN201710468260.5A patent/CN107043345B/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6075044A (en) * | 1997-07-21 | 2000-06-13 | The Regents Of The University Of California | Heterocyclic derivatives as inhibitors of purine salvage phosphoribosyltransferases |
WO2008009935A1 (en) * | 2006-07-19 | 2008-01-24 | Ucl Business Plc | Pharmaceutical compositions and their use |
CN104193650A (en) * | 2014-08-12 | 2014-12-10 | 齐鲁工业大学 | Structure, preparation and application of benzildihydrazone-N,N'-bis(1-formacylnaphthalene) |
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 |
Also Published As
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CN107043345A (en) | 2017-08-15 |
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Effective date of registration: 20201230 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 Industrial University, 3501 University Road, Changqing District, Ji'nan, Shandong Patentee before: Qilu University of Technology |
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Effective date of registration: 20221221 Address after: No. 235, Mingchuan Road, Taohua Town, Feixi County, Hefei, Anhui 231200 Patentee after: Hefei Xiuhe Biotechnology 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. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190705 |