Title:
COUMARINS COMPOUNDS, THE PREPARATION AND THE USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2004/101543
Kind Code:
A1
Abstract:
The present invention relates to 4-substituted chiral courmarins, the preparation and the use thereof. These compounds have the structure of formula I, wherein R is an arly substituted by H, CHO, OCH3, X, NO2, C1-10 alkyl, CN, COOCH3, wherein aryl is phenyl, naphthyl, or aza-aryl; or a courmarin group substituted by R1, R2, R3 or R4; R1, R2, R3, R4 represent H, C1-10 alkyl, X, NO2, CN, OCH3, COOCH3 or OR5 respectively; R2 and R3 may also together be -O-CH2O-; R5 represents H, C1-10 alkyl; X is halogen. Thecompounds of the present invention have evident antifungal activities.
Inventors:
LIN GUOQIANG (CN)
LEI JIANGUANG (CN)
XU MINGHUA (CN)
REN JIN (CN)
LEI JIANGUANG (CN)
XU MINGHUA (CN)
REN JIN (CN)
Application Number:
PCT/CN2004/000491
Publication Date:
November 25, 2004
Filing Date:
May 17, 2004
Export Citation:
Assignee:
SHANGHAI INST ORGANIC CHEM (CN)
LIN GUOQIANG (CN)
LEI JIANGUANG (CN)
XU MINGHUA (CN)
REN JIN (CN)
LIN GUOQIANG (CN)
LEI JIANGUANG (CN)
XU MINGHUA (CN)
REN JIN (CN)
International Classes:
A61P31/10; C07D311/18; (IPC1-7): C07D311/18; A61K31/343; A61P31/10
Domestic Patent References:
| WO1998025608A1 | 1998-06-18 | |||
| WO1998004572A1 | 1998-02-05 |
Foreign References:
| JP2876129B2 | 1999-03-31 | |||
| US4083857A | 1978-04-11 | |||
| US5554611A | 1996-09-10 |
Other References:
LEI JIANGUANG ET AL.: "The first total synthesis of 4,4-bisisofraxidin", CHINESE J. CHEM., vol. 20, 2002, pages 1263 - 1267
PHARKPHOOM P. ET AL.: "A new biscoumarin from impatiens balsamina root cultures", PLANTA MEDICA, vol. 64, 1998, pages 774 - 775
PARADKAR M.V. ET AL.: "A facile synthesis of new [4,4-bi-2H-1-benzopyran]-2,2-diones", SYNTHETIC COMMUNICATIONS, vol. 18, no. 6, 1988, pages 589 - 596
ZHANG YANYING ET AL.: "A study on the synthesis and spectra characteristics of coumarins", DYESTUFFS AND COLORATION, vol. 40, no. 2, 2002, pages 68 - 70
MIN-LIANG YAO ET AL.: "A novel and convenient method to 4-substituted coumarins", HETEROATOM. CHEM., vol. 11, no. 6, 2000, pages 380 - 382
LAURENT SCHIO ET AL.: "Tosylates in palladium-catalysed coupling reactions. Applications to the synthesis of arylcoumarin inhibitors of gyrase B", TETRAHEDRON LETT., vol. 41, 2000, pages 1543 - 1547, XP004189792, DOI: doi:10.1016/S0040-4039(99)02351-5
JAYATI ET AL.: "Palladium in organic synthesis : part IV palladium (0) catalyzed arylation of coumarin", INDIAN J. CHEM., vol. 35B, 1996, pages 588 - 589
BOSE ET AL.: "Synthesis of 4-phenylcoumarins", INDIAN J. CHEM., vol. 29B, 1990, pages 422 - 424
DERVILLA: "A new approach to neoflavonoid synthesis", J. CHEM. SOC. PERKIN TRANS., vol. 1, 1990, pages 2851 - 2852
ZHANG YANYING ET AL.: "Current development in synthetic methods for arylcoumarins", DYESTUFFS AND COLORATION, vol. 40, no. 1, 2002, pages 39 - 41
MOHAMMAD ET AL.: "Biomimetic synthesis of some novel coumarin dimers", TETRAHEDRON, vol. 52, no. 11, 1999, pages 3991 - 3996, XP004196633, DOI: doi:10.1016/S0040-4020(96)00063-4
JOHANNES: "Synthesis of the natural coumarins (E)-suberenol, cyclobisuberodiene and two other related new coumarins", J. REISCH, NATURAL PRODUCTS CHEM., vol. 139, 1990, pages 931 - 933
SOROUSH ET AL.: "Synthesis and antifungal activity of coumarins and angular furanocoumarins", BIOORG. MED. CHEM., vol. 7, 1999, pages 1933 - 1940
HAO XIAOJIANG ET AL.: "The chemical constituents of boenninghausenia sessilicarpa", ACTA BOTANICA YUNNANICA, vol. 16, no. 3, 1994, pages 310 - 312
ZHAO YAJUN ET AL.: "A reverse friedel-crafts reaction and the synthesis of enzo[h]coumarin", ACTA SCIENTARIUM NATURALIUM UNIVERSITATIS PERKINENSIS, vol. 30, no. 4, 1994, pages 421 - 424
See also references of EP 1634878A4
PHARKPHOOM P. ET AL.: "A new biscoumarin from impatiens balsamina root cultures", PLANTA MEDICA, vol. 64, 1998, pages 774 - 775
PARADKAR M.V. ET AL.: "A facile synthesis of new [4,4-bi-2H-1-benzopyran]-2,2-diones", SYNTHETIC COMMUNICATIONS, vol. 18, no. 6, 1988, pages 589 - 596
ZHANG YANYING ET AL.: "A study on the synthesis and spectra characteristics of coumarins", DYESTUFFS AND COLORATION, vol. 40, no. 2, 2002, pages 68 - 70
MIN-LIANG YAO ET AL.: "A novel and convenient method to 4-substituted coumarins", HETEROATOM. CHEM., vol. 11, no. 6, 2000, pages 380 - 382
LAURENT SCHIO ET AL.: "Tosylates in palladium-catalysed coupling reactions. Applications to the synthesis of arylcoumarin inhibitors of gyrase B", TETRAHEDRON LETT., vol. 41, 2000, pages 1543 - 1547, XP004189792, DOI: doi:10.1016/S0040-4039(99)02351-5
JAYATI ET AL.: "Palladium in organic synthesis : part IV palladium (0) catalyzed arylation of coumarin", INDIAN J. CHEM., vol. 35B, 1996, pages 588 - 589
BOSE ET AL.: "Synthesis of 4-phenylcoumarins", INDIAN J. CHEM., vol. 29B, 1990, pages 422 - 424
DERVILLA: "A new approach to neoflavonoid synthesis", J. CHEM. SOC. PERKIN TRANS., vol. 1, 1990, pages 2851 - 2852
ZHANG YANYING ET AL.: "Current development in synthetic methods for arylcoumarins", DYESTUFFS AND COLORATION, vol. 40, no. 1, 2002, pages 39 - 41
MOHAMMAD ET AL.: "Biomimetic synthesis of some novel coumarin dimers", TETRAHEDRON, vol. 52, no. 11, 1999, pages 3991 - 3996, XP004196633, DOI: doi:10.1016/S0040-4020(96)00063-4
JOHANNES: "Synthesis of the natural coumarins (E)-suberenol, cyclobisuberodiene and two other related new coumarins", J. REISCH, NATURAL PRODUCTS CHEM., vol. 139, 1990, pages 931 - 933
SOROUSH ET AL.: "Synthesis and antifungal activity of coumarins and angular furanocoumarins", BIOORG. MED. CHEM., vol. 7, 1999, pages 1933 - 1940
HAO XIAOJIANG ET AL.: "The chemical constituents of boenninghausenia sessilicarpa", ACTA BOTANICA YUNNANICA, vol. 16, no. 3, 1994, pages 310 - 312
ZHAO YAJUN ET AL.: "A reverse friedel-crafts reaction and the synthesis of enzo[h]coumarin", ACTA SCIENTARIUM NATURALIUM UNIVERSITATIS PERKINENSIS, vol. 30, no. 4, 1994, pages 421 - 424
See also references of EP 1634878A4
Attorney, Agent or Firm:
SHANGHAI KAIJI INTELLECTUAL PROPERTY AGENT CO., LTD. (188 Nandandong Road, Shanghai 0, CN)
Download PDF: