CN109912451B - 4-羟基二苯甲酮腙-水杨醛席夫碱的制备和用途 - Google Patents
4-羟基二苯甲酮腙-水杨醛席夫碱的制备和用途 Download PDFInfo
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- CN109912451B CN109912451B CN201910274655.0A CN201910274655A CN109912451B CN 109912451 B CN109912451 B CN 109912451B CN 201910274655 A CN201910274655 A CN 201910274655A CN 109912451 B CN109912451 B CN 109912451B
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- hydroxybenzophenone
- hydrazone
- phase synthesis
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- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000002262 Schiff base Substances 0.000 title description 11
- -1 4-hydroxybenzophenone hydrazone-salicylaldehyde Schiff base Chemical class 0.000 title description 4
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- AIUATHLWVBCHAE-KIRJRVOOSA-N 2-[(E)-[(Z)-[(4-hydroxyphenyl)-phenylmethylidene]hydrazinylidene]methyl]phenol Chemical compound OC1=CC=C(C=C1)\C(\C1=CC=CC=C1)=N/N=C/C1=C(C=CC=C1)O AIUATHLWVBCHAE-KIRJRVOOSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 7
- 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
- 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 9
- MBBAQOHSSWERBC-UHFFFAOYSA-N 4-(C-phenylcarbonohydrazonoyl)phenol Chemical compound OC1=CC=C(C=C1)C(C1=CC=CC=C1)=NN MBBAQOHSSWERBC-UHFFFAOYSA-N 0.000 claims description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-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
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 201000007270 liver cancer Diseases 0.000 claims description 3
- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 150000003839 salts Chemical class 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
- 239000003960 organic solvent Substances 0.000 description 8
- 150000004753 Schiff bases Chemical class 0.000 description 7
- 239000000463 material Substances 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
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- 238000010586 diagram Methods 0.000 description 3
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- 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
- 239000002994 raw material Substances 0.000 description 3
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- 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
- 238000004458 analytical method Methods 0.000 description 2
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- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 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
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- 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
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- 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
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- 238000000921 elemental analysis Methods 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
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- 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
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN201910274655.0A CN109912451B (zh) | 2019-04-08 | 2019-04-08 | 4-羟基二苯甲酮腙-水杨醛席夫碱的制备和用途 |
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CN201910274655.0A CN109912451B (zh) | 2019-04-08 | 2019-04-08 | 4-羟基二苯甲酮腙-水杨醛席夫碱的制备和用途 |
Publications (2)
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CN109912451A CN109912451A (zh) | 2019-06-21 |
CN109912451B true CN109912451B (zh) | 2021-11-30 |
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- 2019-04-08 CN CN201910274655.0A patent/CN109912451B/zh active Active
Non-Patent Citations (2)
Title |
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A colorimetric and turn-on fluorescent chemosensor for selective detection of Hg2+:theoretical studies and intracellular applications;Rimi Roy等;《RSC Adv.》;20150731;第67833-67840页 * |
Specific Fluorescence Probes for Lipid Droplets Based on Simple AIEgens;Zhiming Wang等;《ACS Appl. Mater. Interfaces》;20160407;第10193-10200页 * |
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Effective date of registration: 20230104 Address after: Room 3115, No. 135, Ward Avenue, Ping'an Street, Changqing District, Jinan, Shandong 250300 Patentee after: Shandong Jiqing Technology Service Co.,Ltd. Address before: 250353 Qilu University of technology, Changqing University Town, Jinan City, Shandong Province Patentee before: Qilu University of Technology |
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Denomination of invention: Preparation and application of 4-hydroxybenzophenone hydrazone salicylaldehyde Schiff base Effective date of registration: 20231122 Granted publication date: 20211130 Pledgee: Qilu bank Limited by Share Ltd. Ji'nan Changqing branch Pledgor: Shandong Jiqing Technology Service Co.,Ltd. Registration number: Y2023980067041 |
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Granted publication date: 20211130 Pledgee: Qilu bank Limited by Share Ltd. Ji'nan Changqing branch Pledgor: Shandong Jiqing Technology Service Co.,Ltd. Registration number: Y2023980067041 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right |