CN115260038B - 一种治疗食管癌的新型查尔酮衍生物及其制备方法和医药用途 - Google Patents
一种治疗食管癌的新型查尔酮衍生物及其制备方法和医药用途 Download PDFInfo
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- CN115260038B CN115260038B CN202210843796.1A CN202210843796A CN115260038B CN 115260038 B CN115260038 B CN 115260038B CN 202210843796 A CN202210843796 A CN 202210843796A CN 115260038 B CN115260038 B CN 115260038B
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- chalcone derivative
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- esophageal cancer
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- GVSPXQVUXHMUMA-MDWZMJQESA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GVSPXQVUXHMUMA-MDWZMJQESA-N 0.000 title claims abstract description 46
- 208000000461 Esophageal Neoplasms Diseases 0.000 title claims abstract description 29
- 206010030155 Oesophageal carcinoma Diseases 0.000 title claims abstract description 29
- 201000004101 esophageal cancer Diseases 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 10
- 208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims abstract description 8
- 208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims abstract description 8
- 206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims abstract description 7
- 229940079593 drug Drugs 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 150000001788 chalcone derivatives Chemical class 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- -1 aromatic acetophenone compounds Chemical class 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003935 benzaldehydes Chemical class 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 abstract description 22
- 238000011282 treatment Methods 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 12
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- 238000002474 experimental method Methods 0.000 abstract description 4
- 238000001727 in vivo Methods 0.000 abstract description 4
- 206010061309 Neoplasm progression Diseases 0.000 abstract description 3
- 231100000673 dose–response relationship Toxicity 0.000 abstract description 3
- 238000010172 mouse model Methods 0.000 abstract description 3
- 230000005751 tumor progression Effects 0.000 abstract description 3
- 238000012404 In vitro experiment Methods 0.000 abstract description 2
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- 241000699670 Mus sp. Species 0.000 description 7
- 230000006907 apoptotic process Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 4
- 238000010609 cell counting kit-8 assay Methods 0.000 description 4
- 150000001789 chalcones Chemical class 0.000 description 4
- 235000005513 chalcones Nutrition 0.000 description 4
- 108010087230 Sincalide Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 3
- 102000004121 Annexin A5 Human genes 0.000 description 2
- 108090000672 Annexin A5 Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000001640 apoptogenic effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- 238000000684 flow cytometry Methods 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011580 nude mouse model Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012342 propidium iodide staining Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 1
- 238000011728 BALB/c nude (JAX™ mouse strain) Methods 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 230000004668 G2/M phase Effects 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000025084 cell cycle arrest Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
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- 230000003111 delayed effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ketene group Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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CN202210843796.1A CN115260038B (zh) | 2022-07-18 | 2022-07-18 | 一种治疗食管癌的新型查尔酮衍生物及其制备方法和医药用途 |
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CN202210843796.1A CN115260038B (zh) | 2022-07-18 | 2022-07-18 | 一种治疗食管癌的新型查尔酮衍生物及其制备方法和医药用途 |
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CN115260038B true CN115260038B (zh) | 2024-02-02 |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63267749A (ja) * | 1987-04-09 | 1988-11-04 | メレルダウファーマスーティカルズ インコーポレーテッド | カルコン誘導体で痛風を治療する治療剤 |
WO2013054998A1 (ko) * | 2011-10-13 | 2013-04-18 | 건국대학교 산학협력단 | 신규한 칼콘 유도체 및 이를 유효성분으로 하는 항암제 조성물 |
KR20140147619A (ko) * | 2013-06-20 | 2014-12-30 | 이화여자대학교 산학협력단 | 신규한 칼콘 유도체 및 이의 용도 |
WO2016020427A1 (en) * | 2014-08-05 | 2016-02-11 | Charité - Universitätsmedizin Berlin | Macc1 inhibitors and use thereof in the treatment of cancer |
CN106496052A (zh) * | 2016-10-19 | 2017-03-15 | 汕头大学医学院 | 一种査尔酮类化合物及其制备方法和应用 |
CN109705017A (zh) * | 2019-01-22 | 2019-05-03 | 中美(河南)荷美尔肿瘤研究院 | 一种查尔酮吲哚衍生物在制备抗肿瘤药物中的应用 |
CN111269104A (zh) * | 2020-01-23 | 2020-06-12 | 温州医科大学 | 一种查尔酮类似物及其应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011137516A1 (en) * | 2010-05-03 | 2011-11-10 | The Royal Institution For The Advancement Of Learning / Mcgill University | Flavonoid dimers and their use |
-
2022
- 2022-07-18 CN CN202210843796.1A patent/CN115260038B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63267749A (ja) * | 1987-04-09 | 1988-11-04 | メレルダウファーマスーティカルズ インコーポレーテッド | カルコン誘導体で痛風を治療する治療剤 |
WO2013054998A1 (ko) * | 2011-10-13 | 2013-04-18 | 건국대학교 산학협력단 | 신규한 칼콘 유도체 및 이를 유효성분으로 하는 항암제 조성물 |
KR20140147619A (ko) * | 2013-06-20 | 2014-12-30 | 이화여자대학교 산학협력단 | 신규한 칼콘 유도체 및 이의 용도 |
WO2016020427A1 (en) * | 2014-08-05 | 2016-02-11 | Charité - Universitätsmedizin Berlin | Macc1 inhibitors and use thereof in the treatment of cancer |
CN106496052A (zh) * | 2016-10-19 | 2017-03-15 | 汕头大学医学院 | 一种査尔酮类化合物及其制备方法和应用 |
CN109705017A (zh) * | 2019-01-22 | 2019-05-03 | 中美(河南)荷美尔肿瘤研究院 | 一种查尔酮吲哚衍生物在制备抗肿瘤药物中的应用 |
CN111269104A (zh) * | 2020-01-23 | 2020-06-12 | 温州医科大学 | 一种查尔酮类似物及其应用 |
Non-Patent Citations (6)
Title |
---|
Design, Synthesis and Molecular Docking of Chalcone Derivatives as Potential Anticancer Agents;Heba M. Abosalim,et al.;《ChemistrySelect》;第6卷;第888-895页 * |
Heba M. Abosalim,et al..Design, Synthesis and Molecular Docking of Chalcone Derivatives as Potential Anticancer Agents.《ChemistrySelect》.2021,第6卷第888-895页. * |
Retrochalcone Echinatin Triggers Apoptosis of Esophageal Squamous Cell Carcinoma via ROSand ER Stress-Mediated Signaling Pathways;Ah-Won Kwak,et al.;《Molecules》;第24卷(第22期);第1-14页 * |
Yan Yang,et al..A novel synthetic chalcone derivative, 2,4,6‑trimethoxy‑4′‑nitrocha lcone (Ch‑19), exerted anti‑tumor effects through stimulating ROS accumulation and inducing apoptosis in esophageal cancer cells.《Cell Stress and Chaperones》.2022,第27卷645-657. * |
异甘草素抗食管癌细胞活性及其机制研究;陈利军 等;《现代肿瘤医学》;第26卷(第7期);第1012-1015页 * |
查尔酮衍生物cc-85调节活性氧诱导食管癌细胞凋亡的作用机制研究;李莉莉;《中国优秀硕士学位论文全文数据库 医药卫生科技辑》(第11期);第E057-48页 * |
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