CN105017350B - 一种糖基吡啶类化合物及其制备和应用 - Google Patents
一种糖基吡啶类化合物及其制备和应用 Download PDFInfo
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- CN105017350B CN105017350B CN201410158407.7A CN201410158407A CN105017350B CN 105017350 B CN105017350 B CN 105017350B CN 201410158407 A CN201410158407 A CN 201410158407A CN 105017350 B CN105017350 B CN 105017350B
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- China
- Prior art keywords
- glycosyl
- pyridine compounds
- formula
- pyridine
- preparation
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- 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.)
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- -1 glycosyl pyridine compounds Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 238000006555 catalytic reaction Methods 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- DTUANRRVVJRTJS-UHFFFAOYSA-N 2-pyridin-3-ylbenzaldehyde Chemical class O=CC1=CC=CC=C1C1=CC=CN=C1 DTUANRRVVJRTJS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- HZIAZFYUXWXFEQ-SSPAHAAFSA-N NNC(=O)C1=CC=CC=C1.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O Chemical compound NNC(=O)C1=CC=CC=C1.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O HZIAZFYUXWXFEQ-SSPAHAAFSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 230000002401 inhibitory effect Effects 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 9
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 9
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- KHPAGGHFIDLUMB-UHFFFAOYSA-N 2-chloropyridine-3-carbaldehyde Chemical compound ClC1=NC=CC=C1C=O KHPAGGHFIDLUMB-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 208000037841 lung tumor Diseases 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- NXMFJCRMSDRXLD-UHFFFAOYSA-N 2-aminopyridine-3-carbaldehyde Chemical compound NC1=NC=CC=C1C=O NXMFJCRMSDRXLD-UHFFFAOYSA-N 0.000 description 1
- GNFWMEFWZWXLIN-UHFFFAOYSA-N 2-bromopyridine-3-carbaldehyde Chemical class BrC1=NC=CC=C1C=O GNFWMEFWZWXLIN-UHFFFAOYSA-N 0.000 description 1
- AFWWKZCPPRPDQK-UHFFFAOYSA-N 6-chloropyridine-3-carbaldehyde Chemical compound ClC1=CC=C(C=O)C=N1 AFWWKZCPPRPDQK-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CN201410158407.7A CN105017350B (zh) | 2014-04-18 | 2014-04-18 | 一种糖基吡啶类化合物及其制备和应用 |
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CN201410158407.7A CN105017350B (zh) | 2014-04-18 | 2014-04-18 | 一种糖基吡啶类化合物及其制备和应用 |
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CN105017350A CN105017350A (zh) | 2015-11-04 |
CN105017350B true CN105017350B (zh) | 2018-03-16 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1764644A (zh) * | 2003-02-05 | 2006-04-26 | 新南创新私人有限公司 | 金属离子螯合剂及其医疗用途 |
CN104109119A (zh) * | 2013-04-22 | 2014-10-22 | 中国医学科学院药物研究所 | N′-芳甲酰基邻吡啶酰肼衍生物及其制法和药物组合物与用途 |
-
2014
- 2014-04-18 CN CN201410158407.7A patent/CN105017350B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1764644A (zh) * | 2003-02-05 | 2006-04-26 | 新南创新私人有限公司 | 金属离子螯合剂及其医疗用途 |
CN104109119A (zh) * | 2013-04-22 | 2014-10-22 | 中国医学科学院药物研究所 | N′-芳甲酰基邻吡啶酰肼衍生物及其制法和药物组合物与用途 |
Non-Patent Citations (4)
Title |
---|
"Hydrazonechelators for the treatment of iron overload disorders: iron coordination chemistry and biological activity";Paul V. Bernhardt, et al.,;《Dalton Trans》;20070608;第30卷(第30期);第3205–3336页 * |
"Identification of the di-pyridyl ketone isonicotinoylhydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents";Erika M. Becker, et al.,;《British Journal of Pharmacology》;20031231;第138卷(第5期);第819 -830页 * |
"Synthesis of 4-Methoxybenzoylhydrazones and Evaluation of Their Antiglycation Activity";M. Taha et al.,;《Molecules》;20140121;第19卷;第1286-1301页 * |
"糖基化药物与糖基化技术的研究进展";邓玲玲等,;《中国生化药物杂志》;20111231;第32卷(第1期);第72-75页 * |
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Effective date of registration: 20210105 Address after: 311100 rooms 1010, 1012 and 1016, block F, building 1, 1378 Wenyi West Road, Cangqian street, Yuhang District, Hangzhou City, Zhejiang Province Patentee after: Hangzhou xinbeisi biomedical Co.,Ltd. Address before: 310018 No. 16 Xuelin Street, Jianggan District, Hangzhou City, Zhejiang Province Patentee before: Hangzhou Normal University |
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Denomination of invention: A glycosylpyridine compound and its preparation and application Granted publication date: 20180316 Pledgee: Guotou Taikang Trust Co.,Ltd. Pledgor: Hangzhou xinbeisi biomedical Co.,Ltd. Registration number: Y2024980011343 |