Title:
4-SUBSTITUED COUMARIN DERIVATIVE, AND PREPARATION METHOD AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2017/049871
Kind Code:
A1
Abstract:
The present invention provides a 4-substituted coumarin derivative having a structural formula as shown by formula 1, and also provides a preparation method and use of the 4-substituted coumarin derivative. Said compound has a stronger anti-tumor activity, better inhibits microtubule assembly, and thus can be used to prepare a pharmaceutical against allergy and drug-resistant tumor cells.
Inventors:
CHEN LIJUAN (CN)
WEI YUQUAN (CN)
WEI YUQUAN (CN)
Application Number:
PCT/CN2016/074796
Publication Date:
March 30, 2017
Filing Date:
February 29, 2016
Export Citation:
Assignee:
SI CHUAN UNIV (CN)
International Classes:
C07D409/04; A61K31/37; A61K31/4709; A61K31/55; A61P29/00; A61P35/00; C07D311/16; C07D405/04; C07D407/04; C07D407/14; C07D409/14
Domestic Patent References:
| WO2012136910A1 | 2012-10-11 | |||
| WO2005103705A2 | 2005-11-03 | |||
| WO2014153533A1 | 2014-09-25 |
Foreign References:
| DE2331438A1 | 1974-01-10 | |||
| CN101657443A | 2010-02-24 | |||
| CN102627638A | 2012-08-08 | |||
| US5527827A | 1996-06-18 | |||
| CN102746281A | 2012-10-24 |
Other References:
MANJUNATH GHATE ET AL.: "Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti inflammatory agents", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 31 December 2003 (2003-12-31), pages 297 - 302, XP004416740
O LGA G. GANINA ET AL.: "Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor", BIOORGANIC & MEDICINAL CHEMISTRY, 5 September 2008 (2008-09-05), pages 8806 - 8812, XP025468935
DEMETRIS VRAKAS ET AL.: "Retention of substituted coumarins using immobilized artificial membrane (IAM) chromatography: A comparative study with n-octanol partitioning and reversed-phase HPLC and TLC", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 11 July 2005 (2005-07-11), pages 908 - 913, XP027718792
KRISHNAMOORTHY SIVAKUMAR ET AL.: "A Fluorogenic 1, 3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes", ORGANIC LETTERS, 4 November 2004 (2004-11-04), pages 4603 - 4606, XP002995168
DEMETRIOS N. NICOLAIDES ET AL.: "Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1, 2, 4-oxadiazole derivatives", J. MED. CHEM., vol. 33, 31 December 1998 (1998-12-31), pages 715 - 724, XP004140826
DEBORAH D. SOTO-ORTEGA ET AL.: "Inhibition of amyloid-b aggregation by coumarin analogs can be manipulated by functionalization of the aromatic center", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 19, 12 March 2011 (2011-03-12), pages 2596 - 2602, XP055373308
JIE SHENG ET AL.: "Generation of 4-substituted coumarins via CeH bond activation under palladium bromideecopper(I) bromide cooperative catalysis", TETRAHEDRON, vol. 69, 21 October 2013 (2013-10-21), pages 10230 - 10234, XP028761498
KOTA SASANO ET AL.: "Palladium(II)-Catalyzed Direct Carboxylation of Alkenyl C H Bonds with C02", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 135, 18 July 2013 (2013-07-18), pages 10954 - 10957, XP055373311
See also references of EP 3354648A4
O LGA G. GANINA ET AL.: "Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor", BIOORGANIC & MEDICINAL CHEMISTRY, 5 September 2008 (2008-09-05), pages 8806 - 8812, XP025468935
DEMETRIS VRAKAS ET AL.: "Retention of substituted coumarins using immobilized artificial membrane (IAM) chromatography: A comparative study with n-octanol partitioning and reversed-phase HPLC and TLC", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 11 July 2005 (2005-07-11), pages 908 - 913, XP027718792
KRISHNAMOORTHY SIVAKUMAR ET AL.: "A Fluorogenic 1, 3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes", ORGANIC LETTERS, 4 November 2004 (2004-11-04), pages 4603 - 4606, XP002995168
DEMETRIOS N. NICOLAIDES ET AL.: "Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1, 2, 4-oxadiazole derivatives", J. MED. CHEM., vol. 33, 31 December 1998 (1998-12-31), pages 715 - 724, XP004140826
DEBORAH D. SOTO-ORTEGA ET AL.: "Inhibition of amyloid-b aggregation by coumarin analogs can be manipulated by functionalization of the aromatic center", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 19, 12 March 2011 (2011-03-12), pages 2596 - 2602, XP055373308
JIE SHENG ET AL.: "Generation of 4-substituted coumarins via CeH bond activation under palladium bromideecopper(I) bromide cooperative catalysis", TETRAHEDRON, vol. 69, 21 October 2013 (2013-10-21), pages 10230 - 10234, XP028761498
KOTA SASANO ET AL.: "Palladium(II)-Catalyzed Direct Carboxylation of Alkenyl C H Bonds with C02", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 135, 18 July 2013 (2013-07-18), pages 10954 - 10957, XP055373311
See also references of EP 3354648A4
Attorney, Agent or Firm:
CHENGDU HONGQIAO PATENT LAW OFFICE (CN)
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