CN107151260A - 一种抗肿瘤活性化合物的制备方法 - Google Patents
一种抗肿瘤活性化合物的制备方法 Download PDFInfo
- Publication number
- CN107151260A CN107151260A CN201710524848.8A CN201710524848A CN107151260A CN 107151260 A CN107151260 A CN 107151260A CN 201710524848 A CN201710524848 A CN 201710524848A CN 107151260 A CN107151260 A CN 107151260A
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- CN
- China
- Prior art keywords
- methanol
- natural products
- dichloromethane
- preparation
- glucose
- Prior art date
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Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 230000000259 anti-tumor effect Effects 0.000 title abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229930014626 natural product Natural products 0.000 claims abstract description 21
- 229930182470 glycoside Natural products 0.000 claims abstract description 19
- 150000002338 glycosides Chemical class 0.000 claims abstract description 19
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 16
- 238000006467 substitution reaction Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 239000008103 glucose Substances 0.000 claims abstract description 13
- 229930182478 glucoside Natural products 0.000 claims abstract description 12
- 150000008131 glucosides Chemical class 0.000 claims abstract description 12
- 230000004224 protection Effects 0.000 claims abstract description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
- 125000003147 glycosyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims abstract description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- -1 saturated sodium bicarbonate, saturated common salt Chemical class 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- GZCGUPFRVQAUEE-VANKVMQKSA-N aldehydo-L-glucose Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-VANKVMQKSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000001472 cytotoxic effect Effects 0.000 abstract 1
- 150000002303 glucose derivatives Chemical class 0.000 abstract 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710524848.8A CN107151260B (zh) | 2017-06-30 | 2017-06-30 | 一种抗肿瘤活性化合物的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710524848.8A CN107151260B (zh) | 2017-06-30 | 2017-06-30 | 一种抗肿瘤活性化合物的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107151260A true CN107151260A (zh) | 2017-09-12 |
| CN107151260B CN107151260B (zh) | 2020-09-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710524848.8A Active CN107151260B (zh) | 2017-06-30 | 2017-06-30 | 一种抗肿瘤活性化合物的制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107151260B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108929857A (zh) * | 2017-05-26 | 2018-12-04 | 中国海洋大学 | 一种柳珊瑚来源的海洋真菌及其在制备拓扑异构酶i抑制剂中的应用 |
-
2017
- 2017-06-30 CN CN201710524848.8A patent/CN107151260B/zh active Active
Non-Patent Citations (2)
| Title |
|---|
| SAGAR D. NALE，等: ""Synthesis of tyrosyl-DNA phosphodiesterase I inhibitors"", 《TETRAHEDRON LETTERS》 * |
| 李化军: ""3-取代槲皮素衍生物的合成研究"", 《中国优秀博硕士学位论文全文数据库（硕士）医药卫生科技辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108929857A (zh) * | 2017-05-26 | 2018-12-04 | 中国海洋大学 | 一种柳珊瑚来源的海洋真菌及其在制备拓扑异构酶i抑制剂中的应用 |
| CN108929857B (zh) * | 2017-05-26 | 2021-10-29 | 中国海洋大学 | 一种柳珊瑚来源的海洋真菌及其在制备拓扑异构酶i抑制剂中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107151260B (zh) | 2020-09-15 |
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Address after: 257093 Binhai New District, Lijin County, Dongying City, Shandong Province (Diaokou Township Residence) Applicant after: SHANDONG DOYE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Applicant after: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. Address before: 257093 Binhai New District, Lijin County, Dongying City, Shandong Province (Diaokou Township Residence) Applicant before: DONGYING DAOYI BIOLOGICAL MEDICINE TECHNOLOGY Co.,Ltd. Applicant before: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20200812 Address after: 261053 Shandong city of Weifang province Baotong Street No. 7166 Applicant after: WEIFANG MEDICAL University Applicant after: SHANDONG DOYE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Applicant after: Shandong Daozhen Pharmaceutical Technology Co.,Ltd. Applicant after: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. Address before: Dongying City, Shandong province 257093 Binhai Lijin County (diaokouhe Township resident) Applicant before: SHANDONG DOYE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Applicant before: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. |
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Denomination of invention: A preparation method of antitumor compound Effective date of registration: 20210224 Granted publication date: 20200915 Pledgee: Industrial and Commercial Bank of China Limited Shouguang sub branch Pledgor: Shandong Daozhen Pharmaceutical Technology Co.,Ltd. Registration number: Y2021980001298 |
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Address after: 261053 No. 7166 Baotong West Street, Weifang City, Shandong Province Patentee after: WEIFANG MEDICAL University Patentee after: Shandong Daohe Pharmaceutical Co.,Ltd. Patentee after: Daohe (Weifang) Pharmaceutical Technology Co.,Ltd. Patentee after: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. Address before: 261053 No. 7166 Baotong West Street, Weifang City, Shandong Province Patentee before: WEIFANG MEDICAL University Patentee before: SHANDONG DOYE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Patentee before: Shandong Daozhen Pharmaceutical Technology Co.,Ltd. Patentee before: WEIFANG HONGNUO HETAI NEW MATERIAL SCIENCE AND TECHNOLOGY Co.,Ltd. |
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Date of cancellation: 20211124 Granted publication date: 20200915 Pledgee: Industrial and Commercial Bank of China Limited Shouguang sub branch Pledgor: Shandong Daozhen Pharmaceutical Technology Co.,Ltd. Registration number: Y2021980001298 |
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Denomination of invention: A preparation method of antitumor active compound Effective date of registration: 20211126 Granted publication date: 20200915 Pledgee: Industrial and Commercial Bank of China Limited Shouguang sub branch Pledgor: Daohe (Weifang) Pharmaceutical Technology Co.,Ltd. Registration number: Y2021980013408 |
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Date of cancellation: 20221019 Granted publication date: 20200915 Pledgee: Industrial and Commercial Bank of China Limited Shouguang sub branch Pledgor: Daohe (Weifang) Pharmaceutical Technology Co.,Ltd. Registration number: Y2021980013408 |
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Application publication date: 20170912 Assignee: Shandong Xindao Pharmaceutical Technology Co.,Ltd. Assignor: Shandong Daohe Pharmaceutical Co.,Ltd. Contract record no.: X2022980019300 Denomination of invention: Preparation of an anti-tumor active compound Granted publication date: 20200915 License type: Common License Record date: 20221024 |
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