JPS63196576A - Furalnaphthoquinone derivative and carcinostatic agent and production thereof - Google Patents
Furalnaphthoquinone derivative and carcinostatic agent and production thereofInfo
- Publication number
- JPS63196576A JPS63196576A JP2859587A JP2859587A JPS63196576A JP S63196576 A JPS63196576 A JP S63196576A JP 2859587 A JP2859587 A JP 2859587A JP 2859587 A JP2859587 A JP 2859587A JP S63196576 A JPS63196576 A JP S63196576A
- Authority
- JP
- Japan
- Prior art keywords
- furalnaphthoquinone
- tables
- formulas
- formula
- chemical formulas
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 230000003327 cancerostatic effect Effects 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 4
- 239000000126 substance Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 238000011097 chromatography purification Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 241001530102 Tabebuia Species 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000002021 butanolic extract Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000284 extract Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 methanol Chemical class 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:A furalnaphthoquinone derivative expressed by formula I (R is -OR', -R', formula II or III; R' is H, alkyl or hydroxyalkyl). EXAMPLE:1-(1-Hydroxyethyl)-furalnaphthoquinone. USE:With powerful carcinostatic activity and useful as a carcinostatic agent. PREPARATION:Tree barks of Tabebuia avellanedal Lorenz or Tebebuia impetiginosa of the family Biognoniaceae unique to Sotth America are extracted with lower alcohols, such as methanol, etc., and the resultant extract is then adjusted to pH 8 and distributed with aqueous butanol to separate a butanol extract, which is subsequently subjected to column chromatography using silica gel and purified to afford the aimed compound expressed by formula I.
Description
【発明の詳細な説明】 氏名 塚 １）益 男[Detailed description of the invention] Name Tsuka 1) Masu Oo
Claims (3)
あります▼、▲数式、化学式、表等があります▼で Ｒ′は水素原子、アルキル基及び／又はハイドロオキシ
アルキル基）で表わされるフラルナフトキノン誘導体。(1) The following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is -OR', -R', ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. In ▼, R' is a hydrogen atom, an alkyl group and/or a hydroxyalkyl group), and is a furalnaphthoquinone derivative.
あります▼、▲数式、化学式、表等があります▼で Ｒ′は水素原子、アルキル基及び／又はハイドロオキシ
アルキル基）で表わされるフラルナフトキノン誘導体を
有効成分とする制癌剤。(2) The following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is -OR', -R', ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. An anticancer drug containing a furalnaphthoquinone derivative represented by ▼ (where R' is a hydrogen atom, an alkyl group, and/or a hydroxyalkyl group) as an active ingredient.
抽出し、クロマトグラフによる精製工程を経て次の一般
式で表わされるフラルナフトキノン誘導体を製造する方
法。 ▲数式、化学式、表等があります▼ （式中Ｒは−ＯＲ′、−Ｒ′、▲数式、化学式、表等が
あります▼、▲数式、化学式、表等があります▼で Ｒ′は水素原子、アルキル基及び／又はハイドロオキシ
アルキル基）(3) A method for producing a furalnaphthoquinone derivative represented by the following general formula by extracting the higher plant Ippei Hosch with an organic solvent or water and performing a chromatographic purification process. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R is -OR', -R', ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and R' is a hydrogen atom , alkyl group and/or hydroxyalkyl group)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2859587A JPS63196576A (en) | 1987-02-10 | 1987-02-10 | Furalnaphthoquinone derivative and carcinostatic agent and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2859587A JPS63196576A (en) | 1987-02-10 | 1987-02-10 | Furalnaphthoquinone derivative and carcinostatic agent and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63196576A true JPS63196576A (en) | 1988-08-15 |
Family
ID=12252944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2859587A Pending JPS63196576A (en) | 1987-02-10 | 1987-02-10 | Furalnaphthoquinone derivative and carcinostatic agent and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63196576A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994006786A1 (en) * | 1992-09-18 | 1994-03-31 | Taheebo Japan Co., Ltd. | 2-(1-HYDROXYETHYL)-5-HYDROXYNAPHTO[2,3-b]FURAN-4,9-DIONE AND ANTITUMOR AGENTS COMPRISING THIS COMPOUND |
| US7538234B2 (en) | 2007-05-31 | 2009-05-26 | Taheebo Japan Co., Ltd. | Preparation of Optically active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4, 9-diones having anticancer activities |
| JP2010539095A (en) * | 2007-09-10 | 2010-12-16 | ボストン バイオメディカル， インコーポレイテッド | Novel Stat3 pathway inhibitor and cancer stem cell inhibitor |
| US7910752B2 (en) | 2005-03-16 | 2011-03-22 | Taheebo Japan Co., Ltd. | Anticancer compound, intermediate therefor, and processes for producing these |
| CN107973788A (en) * | 2018-01-09 | 2018-05-01 | 沈阳药科大学 | BBI608 derivatives and its preparation and purposes |
| WO2018096401A1 (en) | 2016-11-22 | 2018-05-31 | Hitoshi Ban | New naphtho[2,3-b]furan derivatives |
| US10017488B2 (en) | 2014-02-07 | 2018-07-10 | Boston Biomedical, Inc. | 3-substituted carbonyl-naphtho[2,3-B]furane derivative or pharmaceutically acceptable salt thereof |
| US10543189B2 (en) | 2013-04-09 | 2020-01-28 | Boston Biomedical, Inc. | 2-acetylnaphtho[2,3-b]furan -4,9-dione for use on treating cancer |
| US10646464B2 (en) | 2017-05-17 | 2020-05-12 | Boston Biomedical, Inc. | Methods for treating cancer |
| WO2020161959A1 (en) * | 2019-02-06 | 2020-08-13 | タヒボジャパン株式会社 | Naphthoquinone compound having antibacterial and antiviral activities and pharmaceutical use thereof |
| US10906914B2 (en) | 2015-01-08 | 2021-02-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Furoquinolinediones as inhibitors of TDP2 |
| US10934309B2 (en) | 2014-03-31 | 2021-03-02 | Sumitomo Dainippon Pharma Oncology, Inc. | Tricyclic quinone derivative |
| US11299469B2 (en) | 2016-11-29 | 2022-04-12 | Sumitomo Dainippon Pharma Oncology, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
-
1987
- 1987-02-10 JP JP2859587A patent/JPS63196576A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| TETRAHEDRON LETTERS=1986 * |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06145162A (en) * | 1992-09-18 | 1994-05-24 | Tahibo Japan Kk | 2-@(3754/24)1-hydroxyethyl-5-hydroxynaphtho(2,3-b) furan-4,5-dione and anticancer medicine containing the same |
| WO1994006786A1 (en) * | 1992-09-18 | 1994-03-31 | Taheebo Japan Co., Ltd. | 2-(1-HYDROXYETHYL)-5-HYDROXYNAPHTO[2,3-b]FURAN-4,9-DIONE AND ANTITUMOR AGENTS COMPRISING THIS COMPOUND |
| US7910752B2 (en) | 2005-03-16 | 2011-03-22 | Taheebo Japan Co., Ltd. | Anticancer compound, intermediate therefor, and processes for producing these |
| US7538234B2 (en) | 2007-05-31 | 2009-05-26 | Taheebo Japan Co., Ltd. | Preparation of Optically active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4, 9-diones having anticancer activities |
| US10377731B2 (en) | 2007-09-10 | 2019-08-13 | Boston Biomedical, Inc. | Compositions and methods for cancer treatment |
| JP2010539095A (en) * | 2007-09-10 | 2010-12-16 | ボストン バイオメディカル， インコーポレイテッド | Novel Stat3 pathway inhibitor and cancer stem cell inhibitor |
| CN105963289A (en) * | 2007-09-10 | 2016-09-28 | 北京强新生物科技有限公司 | Novel group of STAT3 pathway inhibitors and cancer stem cell pathway inhibitors |
| US10851075B2 (en) | 2007-09-10 | 2020-12-01 | Sumitomo Dainippon Pharma Oncology, Inc. | Stat3 pathway inhibitors and cancer stem cell inhibitors |
| US10543189B2 (en) | 2013-04-09 | 2020-01-28 | Boston Biomedical, Inc. | 2-acetylnaphtho[2,3-b]furan -4,9-dione for use on treating cancer |
| US10017488B2 (en) | 2014-02-07 | 2018-07-10 | Boston Biomedical, Inc. | 3-substituted carbonyl-naphtho[2,3-B]furane derivative or pharmaceutically acceptable salt thereof |
| US10683274B2 (en) | 2014-02-07 | 2020-06-16 | Boston Biomedical, Inc. | 3-substituted carbonyl-naphtho[2,3-B]furane derivative or pharmaceutically acceptable salt thereof |
| US10934309B2 (en) | 2014-03-31 | 2021-03-02 | Sumitomo Dainippon Pharma Oncology, Inc. | Tricyclic quinone derivative |
| US10906914B2 (en) | 2015-01-08 | 2021-02-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Furoquinolinediones as inhibitors of TDP2 |
| WO2018096401A1 (en) | 2016-11-22 | 2018-05-31 | Hitoshi Ban | New naphtho[2,3-b]furan derivatives |
| US11299469B2 (en) | 2016-11-29 | 2022-04-12 | Sumitomo Dainippon Pharma Oncology, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| US10646464B2 (en) | 2017-05-17 | 2020-05-12 | Boston Biomedical, Inc. | Methods for treating cancer |
| CN107973788A (en) * | 2018-01-09 | 2018-05-01 | 沈阳药科大学 | BBI608 derivatives and its preparation and purposes |
| WO2020161959A1 (en) * | 2019-02-06 | 2020-08-13 | タヒボジャパン株式会社 | Naphthoquinone compound having antibacterial and antiviral activities and pharmaceutical use thereof |
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