CN102126942B - Method for synthesizing hypericin - Google Patents
Method for synthesizing hypericin Download PDFInfo
- Publication number
- CN102126942B CN102126942B CN 201010600246 CN201010600246A CN102126942B CN 102126942 B CN102126942 B CN 102126942B CN 201010600246 CN201010600246 CN 201010600246 CN 201010600246 A CN201010600246 A CN 201010600246A CN 102126942 B CN102126942 B CN 102126942B
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- CN
- China
- Prior art keywords
- hypericin
- reaction
- described step
- emodin anthrone
- emodin
- 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.)
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- BTXNYTINYBABQR-UHFFFAOYSA-N hypericin Chemical compound C12=C(O)C=C(O)C(C(C=3C(O)=CC(C)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 BTXNYTINYBABQR-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 229940005608 hypericin Drugs 0.000 title claims abstract description 55
- PHOKTTKFQUYZPI-UHFFFAOYSA-N hypericin Natural products Cc1cc(O)c2c3C(=O)C(=Cc4c(O)c5c(O)cc(O)c6c7C(=O)C(=Cc8c(C)c1c2c(c78)c(c34)c56)O)O PHOKTTKFQUYZPI-UHFFFAOYSA-N 0.000 title claims abstract description 55
- SSKVDVBQSWQEGJ-UHFFFAOYSA-N pseudohypericin Natural products C12=C(O)C=C(O)C(C(C=3C(O)=CC(O)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 SSKVDVBQSWQEGJ-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- CBOKHFLBNZMMAA-UHFFFAOYSA-N Emodin anthrone Natural products OC1=CC(O)=CC2=CC3=CC(C)=CC(O)=C3C(O)=C21 CBOKHFLBNZMMAA-UHFFFAOYSA-N 0.000 claims abstract description 28
- LAJSXCAVRQXZIO-UHFFFAOYSA-N emodin anthrone Chemical compound C1=C(O)C=C2CC3=CC(C)=CC(O)=C3C(=O)C2=C1O LAJSXCAVRQXZIO-UHFFFAOYSA-N 0.000 claims abstract description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 18
- RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 claims abstract description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 10
- 229960000583 acetic acid Drugs 0.000 claims abstract description 9
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 2
- YLILOANQCQKPOD-UHFFFAOYSA-N protohypericin Chemical compound C12=C(O)C=C(O)C(C(C3=C(O)C=C(C=C33)C)=O)=C2C3=C2C3=C1C(O)=CC(O)=C3C(=O)C1=C(O)C=C(C)C=C12 YLILOANQCQKPOD-UHFFFAOYSA-N 0.000 abstract 4
- VWDXGKUTGQJJHJ-UHFFFAOYSA-N Catenarin Natural products C1=C(O)C=C2C(=O)C3=C(O)C(C)=CC(O)=C3C(=O)C2=C1O VWDXGKUTGQJJHJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010282 Emodin Substances 0.000 abstract 1
- RBLJKYCRSCQLRP-UHFFFAOYSA-N Emodin-dianthron Natural products O=C1C2=CC(C)=CC(O)=C2C(=O)C2=C1CC(=O)C=C2O RBLJKYCRSCQLRP-UHFFFAOYSA-N 0.000 abstract 1
- YOOXNSPYGCZLAX-UHFFFAOYSA-N Helminthosporin Natural products C1=CC(O)=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O YOOXNSPYGCZLAX-UHFFFAOYSA-N 0.000 abstract 1
- NTGIIKCGBNGQAR-UHFFFAOYSA-N Rheoemodin Natural products C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O NTGIIKCGBNGQAR-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- VASFLQKDXBAWEL-UHFFFAOYSA-N emodin Natural products OC1=C(OC2=C(C=CC(=C2C1=O)O)O)C1=CC=C(C=C1)O VASFLQKDXBAWEL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- PKUBGLYEOAJPEG-UHFFFAOYSA-N physcion Natural products C1=C(C)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O PKUBGLYEOAJPEG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000593508 Garcinia Species 0.000 description 1
- 235000000885 Garcinia xanthochymus Nutrition 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 201010600246 CN102126942B (en) | 2010-12-22 | 2010-12-22 | Method for synthesizing hypericin |
Applications Claiming Priority (1)
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CN 201010600246 CN102126942B (en) | 2010-12-22 | 2010-12-22 | Method for synthesizing hypericin |
Publications (2)
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CN102126942A CN102126942A (en) | 2011-07-20 |
CN102126942B true CN102126942B (en) | 2013-10-23 |
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CN 201010600246 Expired - Fee Related CN102126942B (en) | 2010-12-22 | 2010-12-22 | Method for synthesizing hypericin |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103274920B (en) * | 2013-06-14 | 2014-12-17 | 西北农林科技大学 | Efficient hypericin synthesizing method initiated by monochromatic light |
CN108863741A (en) * | 2017-05-11 | 2018-11-23 | 上海凯伟化工科技有限公司 | A kind of synthetic method of hypericin |
CN108084065B (en) * | 2017-11-21 | 2020-06-16 | 中国农业科学院兰州畜牧与兽药研究所 | Hypericin derivative and preparation method and application thereof |
CN111138262A (en) * | 2020-01-13 | 2020-05-12 | 成都金石缘科技有限公司 | Hypericin synthesis method |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1827574A (en) * | 2006-04-19 | 2006-09-06 | 中国农业科学院兰州畜牧与兽药研究所 | Chemical synthesis process for hypericin and derivatives thereof |
-
2010
- 2010-12-22 CN CN 201010600246 patent/CN102126942B/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1827574A (en) * | 2006-04-19 | 2006-09-06 | 中国农业科学院兰州畜牧与兽药研究所 | Chemical synthesis process for hypericin and derivatives thereof |
Non-Patent Citations (6)
Title |
---|
A microwave-assisted synthesis of phenanthroperylene quinones as exemplified with hypericin;Stefan Aigner et al.;《Monatshefte für Chemie》;20080218;第139卷;第991-993页 * |
Stefan Aigner et al..A microwave-assisted synthesis of phenanthroperylene quinones as exemplified with hypericin.《Monatshefte für Chemie》.2008,第139卷第991-993页. |
汤媛 等.金丝桃素的合成工艺改进.《合成化学》.2009,第17卷(第4期),第498-499、502页. |
汤媛 等.金丝桃素研究进展.《医药导报》.2009,第28卷第65-67页. |
金丝桃素的合成工艺改进;汤媛 等;《合成化学》;20090820;第17卷(第4期);第498-499、502页 * |
金丝桃素研究进展;汤媛 等;《医药导报》;20090518;第28卷;第65-67页 * |
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CN102126942A (en) | 2011-07-20 |
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Effective date of registration: 20140519 Address after: 430079 No. 666, hi tech Avenue, East Lake hi tech Development Zone, Hubei, Wuhan Patentee after: Hubei Shinrezing Pharmaceutical Co., Ltd. Address before: 430068 Wuchang, Hubei Province, South Lake, Li Jia Dun special No. 1 Patentee before: Hubei Industry University |
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Owner name: LIU MINGXING Free format text: FORMER OWNER: HUBEI SHINREZING PHARMACEUTICAL CO., LTD. Effective date: 20140529 |
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Free format text: CORRECT: ADDRESS; FROM: 430079 WUHAN, HUBEI PROVINCE TO: 430068 WUHAN, HUBEI PROVINCE |
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Effective date of registration: 20140529 Address after: 430068 College of food and pharmaceutical engineering, Ministry of light industry, Hubei University of Technology, Hongshan District, Wuhan, Hubei Patentee after: Liu Mingxing Address before: 430079 No. 666, hi tech Avenue, East Lake hi tech Development Zone, Hubei, Wuhan Patentee before: Hubei Shinrezing Pharmaceutical Co., Ltd. |
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Owner name: WUHAN MAIDESEN MEDICAL TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: LIU MINGXING Effective date: 20150217 |
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Free format text: CORRECT: ADDRESS; FROM: 430068 WUHAN, HUBEI PROVINCE TO: 430079 WUHAN, HUBEI PROVINCE |
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Effective date of registration: 20150217 Address after: 430079 No. 666, hi tech Avenue, East Lake hi tech Development Zone, Hubei, Wuhan Patentee after: Wuhan Maidesen Medical Technology Co.,Ltd. Address before: 430068 College of food and pharmaceutical engineering, Ministry of light industry, Hubei University of Technology, Hongshan District, Wuhan, Hubei Patentee before: Liu Mingxing |
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