Title:
RACEMIC AND CHIRAL 3-(2,3-BUTADIENYL)OXYINDOLINONE COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/212974
Kind Code:
A1
Abstract:
A racemic and chiral 3-(2,3-butadienyl)oxyindolinone compound, a method for preparing the compound using a palladium catalyzed coupling reaction and an application thereof. According to the preparation method, 2,3-butadienyl carbonate and oxyindolinone are reacted in an organic solvent using a palladium catalyst, to directly construct a racemic 3-(2,3-butadienyl)oxyindolinone compound in one step; and if the palladium catalyst and a chiral phosphine ligand are reacted in the organic solvent in the system, to directly construct a chiral 3-(2,3-butadienyl)oxyindolinone compound in one step, and these compounds would be easily converted into other complex molecules. The method is easy to operate, the raw materials and reagents are easily available, the substrate has wide universality, the functional group has good compatibility, the reaction has good conversion rate, and the enantioselectivity and chemical selectivity are high. In addition, the 3-(2,3-butadienyl)oxyindolinone compound and related derivatives thereof provided in the present invention can be bonded to Sras-CoV-2 main protein 3CL hydrolase, and have good application prospect in treating human viral infection.
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Inventors:
MA SHENGMING (CN)
LIN JIE (CN)
JIA MINQIANG (CN)
CHENG BAO (CN)
CHEN QIN (CN)
QIAN HUI (CN)
LIN JIE (CN)
JIA MINQIANG (CN)
CHENG BAO (CN)
CHEN QIN (CN)
QIAN HUI (CN)
Application Number:
PCT/CN2021/076006
Publication Date:
October 28, 2021
Filing Date:
February 08, 2021
Export Citation:
Assignee:
UNIV FUDAN (CN)
International Classes:
C07C209/66; A61K31/404; A61P31/12; C07C225/20; C07D209/12
Domestic Patent References:
| WO2010008727A1 | 2010-01-21 |
Foreign References:
| CN102531996A | 2012-07-04 | |||
| CN106588749A | 2017-04-26 | |||
| CN108976123A | 2018-12-11 | |||
| KR20090036001A | 2009-04-13 |
Other References:
TRUNG CAO, ELIZABETH C. LINTON, JOSHUA DEITCH, SIMON BERRITT, AND MARISA C. KOZLOWSKI: "Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 24, 21 December 2012 (2012-12-21), pages 11034 - 11055, XP002760363, ISSN: 0022-3263, DOI: 10.1021/jo302039n
ZHAI YIZHAN, YOU SHU-LI, MA SHENGMING: "Palladium-catalyzed intermolecular allenylation reactions of 2,3-disubstituted indoles and allenyl carbonate", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 17, no. 30, 31 July 2019 (2019-07-31), pages 7128 - 7130, XP055860926, ISSN: 1477-0520, DOI: 10.1039/C9OB01435G
GAO RUN-DUO, ZHAI YIZHAN, YOU SHU-LI, MA SHENGMING: "Palladium-catalyzed intermolecular dearomatic allenylation of hydrocycloalk[ b ]indoles with 2,3-allenyl carbonates", ORGANIC CHEMISTRY FRONTIERS, vol. 5, no. 10, 1 January 2018 (2018-01-01), pages 1664 - 1669, XP055860928, DOI: 10.1039/C8QO00163D
ZHAI YIZHAN, YOU SHU-LI, MA SHENGMING: "Palladium-catalyzed intermolecular allenylation reactions of 2,3-disubstituted indoles and allenyl carbonate", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 17, no. 30, 31 July 2019 (2019-07-31), pages 7128 - 7130, XP055860926, ISSN: 1477-0520, DOI: 10.1039/C9OB01435G
GAO RUN-DUO, ZHAI YIZHAN, YOU SHU-LI, MA SHENGMING: "Palladium-catalyzed intermolecular dearomatic allenylation of hydrocycloalk[ b ]indoles with 2,3-allenyl carbonates", ORGANIC CHEMISTRY FRONTIERS, vol. 5, no. 10, 1 January 2018 (2018-01-01), pages 1664 - 1669, XP055860928, DOI: 10.1039/C8QO00163D
Attorney, Agent or Firm:
MSJLAW OFFICE (CN)
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