CN106083966A - 氟取代含半乳糖苷结构三氮唑类去甲斑蝥素衍生物及其制备方法与应用 - Google Patents
氟取代含半乳糖苷结构三氮唑类去甲斑蝥素衍生物及其制备方法与应用 Download PDFInfo
- Publication number
- CN106083966A CN106083966A CN201610398110.7A CN201610398110A CN106083966A CN 106083966 A CN106083966 A CN 106083966A CN 201610398110 A CN201610398110 A CN 201610398110A CN 106083966 A CN106083966 A CN 106083966A
- Authority
- CN
- China
- Prior art keywords
- galactoside
- fluorine
- methanol
- room temperature
- norcantharidin derivative
- Prior art date
- 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.)
- Granted
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 21
- 239000011737 fluorine Substances 0.000 title claims abstract description 20
- -1 galactoside structure triazole norcantharidin derivative Chemical class 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 18
- 150000008195 galaktosides Chemical group 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- HXBYBCASAVUYKF-YTQLPXDHSA-N (4r,5s,6s,7r)-4,5,6,7,8-pentahydroxyoctane-2,3-dione Chemical compound CC(=O)C(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO HXBYBCASAVUYKF-YTQLPXDHSA-N 0.000 claims abstract description 8
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 7
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229940095758 cantharidin Drugs 0.000 claims description 8
- 229930008397 cantharidin Natural products 0.000 claims description 8
- DHZBEENLJMYSHQ-UHFFFAOYSA-N cantharidine Natural products O1C2CCC1C1(C)C2(C)C(=O)OC1=O DHZBEENLJMYSHQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000005457 ice water Substances 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 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
- 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
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 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 5
- 238000001914 filtration Methods 0.000 claims description 5
- 150000003949 imides 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
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 230000033228 biological regulation Effects 0.000 claims description 3
- 239000003729 cation exchange resin Substances 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
- 238000012544 monitoring process Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 229930182830 galactose Natural products 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
- 239000002904 solvent Substances 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 229920001429 chelating resin Polymers 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
- 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 description 7
- 150000000177 1,2,3-triazoles Chemical class 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 230000004071 biological effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 208000032839 leukemia Diseases 0.000 description 6
- 150000003852 triazoles Chemical class 0.000 description 6
- 210000004881 tumor cell Anatomy 0.000 description 5
- 241001597008 Nomeidae Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 206010009944 Colon cancer Diseases 0.000 description 3
- 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
- 230000008859 change Effects 0.000 description 3
- 208000029742 colonic neoplasm Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 206010017758 gastric cancer Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 201000011549 stomach cancer Diseases 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 0 CC1[C@](C)[C@](N)OC2C1*2 Chemical compound CC1[C@](C)[C@](N)OC2C1*2 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JAABVEXCGCXWRR-UHFFFAOYSA-N norcantharidin Chemical compound C1CC2C3C(=O)OC(=O)C3C1O2 JAABVEXCGCXWRR-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229940125782 compound 2 Drugs 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN201610398110.7A CN106083966B (zh) | 2016-06-06 | 2016-06-06 | 氟取代含半乳糖苷结构三氮唑类去甲斑蝥素衍生物及其制备方法与应用 |
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CN201610398110.7A CN106083966B (zh) | 2016-06-06 | 2016-06-06 | 氟取代含半乳糖苷结构三氮唑类去甲斑蝥素衍生物及其制备方法与应用 |
Publications (2)
Publication Number | Publication Date |
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CN106083966A true CN106083966A (zh) | 2016-11-09 |
CN106083966B CN106083966B (zh) | 2018-10-23 |
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CN201610398110.7A Active CN106083966B (zh) | 2016-06-06 | 2016-06-06 | 氟取代含半乳糖苷结构三氮唑类去甲斑蝥素衍生物及其制备方法与应用 |
Country Status (1)
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CN (1) | CN106083966B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111253415A (zh) * | 2020-03-17 | 2020-06-09 | 遵义医科大学 | 去甲斑蝥素羧酸三氟苄酯及其合成方法和应用 |
Citations (4)
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CN101717411A (zh) * | 2009-11-19 | 2010-06-02 | 绍兴文理学院 | 去甲基斑蝥素衍生物磷酸二钠盐及其合成方法与用途 |
CN101812066A (zh) * | 2010-03-04 | 2010-08-25 | 绍兴文理学院 | 吡唑并n-取代去甲去氢斑蝥素酰亚胺衍生物及其合成方法、活性测试方法与应用 |
CN102276673A (zh) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | 一种2-脱氧-β-D-吡喃葡萄糖基三唑类化合物的制备方法 |
CN104817605A (zh) * | 2015-04-14 | 2015-08-05 | 湖北工程学院 | 2-(1’,2’,3’-三氮唑-4’-氧苄基)-1,3,4,6-o-乙酰基-d-葡萄糖及其制备方法和应用 |
-
2016
- 2016-06-06 CN CN201610398110.7A patent/CN106083966B/zh active Active
Patent Citations (4)
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CN101717411A (zh) * | 2009-11-19 | 2010-06-02 | 绍兴文理学院 | 去甲基斑蝥素衍生物磷酸二钠盐及其合成方法与用途 |
CN101812066A (zh) * | 2010-03-04 | 2010-08-25 | 绍兴文理学院 | 吡唑并n-取代去甲去氢斑蝥素酰亚胺衍生物及其合成方法、活性测试方法与应用 |
CN102276673A (zh) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | 一种2-脱氧-β-D-吡喃葡萄糖基三唑类化合物的制备方法 |
CN104817605A (zh) * | 2015-04-14 | 2015-08-05 | 湖北工程学院 | 2-(1’,2’,3’-三氮唑-4’-氧苄基)-1,3,4,6-o-乙酰基-d-葡萄糖及其制备方法和应用 |
Non-Patent Citations (6)
Title |
---|
LIPING DENG,等: "Disodium Phosphate of Norcantharidin Analogues: Design, Synthesis and their Anticancer Evaluation", 《LETTERS IN DRUG DESIGN & DISCOVERY》 * |
LIPING DENG,等: "Novel 1, 2, 3-Triazole-Linked Norcantharidin Analogues: Synthesis and Evaluation of Growth Inhibition in a Panel of Selected Tumor-Cell Lines", 《LETTERS IN DRUG DESIGN & DISCOVERY》 * |
PERUMAL RAJAKUMAR,等: "Synthesis and In-vitro anti-inflammatory activity of novel glycodendrimers with benzene 1,3,5 carboxamide core and triazole as branching unit", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
RAM JANAM SINGH: "1, 2, 3-TRIAZOLE DERIVATIVES AS POSSIBLE ANTIINFLAMMATORY AGENTS", 《RASAYAN J.CHEM.》 * |
赵岩,等: "去甲斑蝥素主动肝靶向性药物设计研究进展", 《环球中医药》 * |
高建德,等: "《物理药剂学及应用》", 31 May 2014 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111253415A (zh) * | 2020-03-17 | 2020-06-09 | 遵义医科大学 | 去甲斑蝥素羧酸三氟苄酯及其合成方法和应用 |
CN111253415B (zh) * | 2020-03-17 | 2022-08-09 | 遵义医科大学 | 去甲斑蝥素羧酸三氟苄酯及其合成方法和应用 |
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CN106083966B (zh) | 2018-10-23 |
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