CN105906678B - Fluorine substitution triazole norcantharidin derivative of structure containing glucoside and preparation method and application - Google Patents
Fluorine substitution triazole norcantharidin derivative of structure containing glucoside and preparation method and application Download PDFInfo
- Publication number
- CN105906678B CN105906678B CN201610395573.8A CN201610395573A CN105906678B CN 105906678 B CN105906678 B CN 105906678B CN 201610395573 A CN201610395573 A CN 201610395573A CN 105906678 B CN105906678 B CN 105906678B
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- China
- Prior art keywords
- structure containing
- room temperature
- glucoside
- preparation
- methanol
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- 229930182478 glucoside Natural products 0.000 title claims abstract description 20
- 150000008131 glucosides Chemical class 0.000 title claims abstract description 19
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 18
- 239000011737 fluorine Substances 0.000 title claims abstract description 17
- 238000006467 substitution reaction Methods 0.000 title claims abstract description 15
- -1 triazole norcantharidin derivative Chemical class 0.000 title claims abstract description 15
- 125000001153 fluoro group Chemical group F* 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 3
- 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 2
- 230000008676 import Effects 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000005457 ice water Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 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 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 150000003949 imides Chemical class 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 150000002240 furans Chemical class 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 3
- 230000033228 biological regulation Effects 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 230000003292 diminished effect Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- WFBHLGOLOWZMBJ-GVYWOMJSSA-N (4r,5s,6r,7r)-1-bromo-4,5,6,7,8-pentahydroxyoctane-2,3-dione Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(=O)C(=O)CBr WFBHLGOLOWZMBJ-GVYWOMJSSA-N 0.000 claims description 2
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229940071125 manganese acetate Drugs 0.000 claims description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- JAABVEXCGCXWRR-FBXFSONDSA-N rel-norcantharidin Chemical group C1C[C@H]2[C@@H]3C(=O)OC(=O)[C@@H]3[C@@H]1O2 JAABVEXCGCXWRR-FBXFSONDSA-N 0.000 abstract description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 6
- 239000002246 antineoplastic agent Substances 0.000 abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 5
- 150000000177 1,2,3-triazoles Chemical class 0.000 abstract description 4
- 230000003993 interaction Effects 0.000 abstract description 2
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical class C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 208000032839 leukemia Diseases 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229940095758 cantharidin Drugs 0.000 description 4
- 229930008397 cantharidin Natural products 0.000 description 4
- DHZBEENLJMYSHQ-UHFFFAOYSA-N cantharidine Natural products O1C2CCC1C1(C)C2(C)C(=O)OC1=O DHZBEENLJMYSHQ-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 206010033128 Ovarian cancer Diseases 0.000 description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 description 3
- 208000005718 Stomach Neoplasms Diseases 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 206010017758 gastric cancer Diseases 0.000 description 3
- 201000007270 liver cancer Diseases 0.000 description 3
- 208000014018 liver neoplasm Diseases 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 201000011549 stomach cancer Diseases 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000623906 Lytta vesicatoria Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AORTZIIKTZPIQU-UHFFFAOYSA-N 3-butyl-4-methyloxolane-2,5-dione Chemical compound CCCCC1C(C)C(=O)OC1=O AORTZIIKTZPIQU-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010073069 Hepatic cancer Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000002508 compound effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- JAABVEXCGCXWRR-UHFFFAOYSA-N norcantharidin Chemical compound C1CC2C3C(=O)OC(=O)C3C1O2 JAABVEXCGCXWRR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- 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
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/24—Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
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- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CN201610395573.8A CN105906678B (en) | 2016-06-06 | 2016-06-06 | Fluorine substitution triazole norcantharidin derivative of structure containing glucoside and preparation method and application |
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CN201610395573.8A CN105906678B (en) | 2016-06-06 | 2016-06-06 | Fluorine substitution triazole norcantharidin derivative of structure containing glucoside and preparation method and application |
Publications (2)
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CN105906678A CN105906678A (en) | 2016-08-31 |
CN105906678B true CN105906678B (en) | 2018-06-26 |
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CN201610395573.8A Active CN105906678B (en) | 2016-06-06 | 2016-06-06 | Fluorine substitution triazole norcantharidin derivative of structure containing glucoside and preparation method and application |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111233883A (en) * | 2020-03-17 | 2020-06-05 | 遵义医科大学 | Norcantharidin fluorine-containing benzyl ester salt derivative, synthesis method and anti-tumor application |
CN111362962B (en) * | 2020-03-17 | 2022-08-09 | 遵义医科大学 | Tetrafluorobenzyl norcantharidin carboxylate and synthesis method thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101717411A (en) * | 2009-11-19 | 2010-06-02 | 绍兴文理学院 | Methyl-removal cantharidin derivative phosphate disodium salt and synthesis method and application thereof |
CN101812066A (en) * | 2010-03-04 | 2010-08-25 | 绍兴文理学院 | Pyrazolo N-substituted dehydronorcantharidin imide derivative as well as synthesis method, activity test method and application thereof |
CN102276673A (en) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound |
CN104817605A (en) * | 2015-04-14 | 2015-08-05 | 湖北工程学院 | 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and preparation method and application thereof |
-
2016
- 2016-06-06 CN CN201610395573.8A patent/CN105906678B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101717411A (en) * | 2009-11-19 | 2010-06-02 | 绍兴文理学院 | Methyl-removal cantharidin derivative phosphate disodium salt and synthesis method and application thereof |
CN101812066A (en) * | 2010-03-04 | 2010-08-25 | 绍兴文理学院 | Pyrazolo N-substituted dehydronorcantharidin imide derivative as well as synthesis method, activity test method and application thereof |
CN102276673A (en) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound |
CN104817605A (en) * | 2015-04-14 | 2015-08-05 | 湖北工程学院 | 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose and preparation method and application thereof |
Non-Patent Citations (5)
Title |
---|
1, 2, 3-TRIAZOLE DERIVATIVES AS POSSIBLE ANTIINFLAMMATORY AGENTS;Ram Janam Singh;《RASAYAN J.Chem.》;20091231;第2卷(第3期);706-708 * |
Disodium Phosphate of Norcantharidin Analogues: Design, Synthesis and their Anticancer Evaluation;Liping Deng,等;《Letters in Drug Design & Discovery》;20091231;第6卷(第5期);345-352 * |
Novel 1, 2, 3-Triazole-Linked Norcantharidin Analogues: Synthesis and Evaluation of Growth Inhibition in a Panel of Selected Tumor-Cell Lines;Liping Deng,等;《Letters in Drug Design & Discovery》;20081231;第5卷(第3期);225-231 * |
Synthesis and In-vitro anti-inflammatory activity of novel glycodendrimers with benzene 1,3,5 carboxamide core and triazole as branching unit;Perumal Rajakumar,等;《European Journal of Medicinal Chemistry》;20110626;第46卷;4687-4695 * |
去甲斑蝥素主动肝靶向性药物设计研究进展;赵岩,等;《环球中医药》;20141130;第7卷(第11期);889-892 * |
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Effective date of registration: 20240328 Address after: 529100, underground, No. 23 Longchang Road, Huicheng, Xinhui District, Jiangmen City, Guangdong Province Patentee after: Gangzhou Environmental Protection Service Co.,Ltd. in Xinhui District Jiangmen City Country or region after: China Address before: Room 314-1, dantaihu building (Wuluo Science Park), No.9, Taihu East Road, Wuzhong District, Suzhou City, Jiangsu Province, 215100 Patentee before: Suzhou ruipengcheng Technology Co.,Ltd. Country or region before: China |