Title:
TAXAMAIRIN ANALOGS AND METHODS OF PREPARATION AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/207921
Kind Code:
A1
Abstract:
Taxamairin analogs useful in the treatment of cancer, pharmaceutical compositions including the same, methods of use thereof, and methods of preparation are provided. An efficient and scalable semi-synthesis of taxamairin compounds and analogs thereof from readily available commercial starting materials is provided. The synthesis involves low cost and relatively non-toxic reagents and is capable of synthesizing taxamairin A and taxamairin B and analogs thereof on multi-gram scale in yields up 12%and 21%, respectively.
Inventors:
LEE CHI SING (CN)
GE SIYUAN (CN)
ZHUANG ANDREW-GO (CN)
GE SIYUAN (CN)
ZHUANG ANDREW-GO (CN)
Application Number:
PCT/CN2023/090388
Publication Date:
November 02, 2023
Filing Date:
April 24, 2023
Export Citation:
Assignee:
UNIV HONG KONG BAPTIST UNIV (CN)
International Classes:
C07C69/013; A61K31/015; A61K31/215; A61P35/00; C07C37/00; C07C39/19; C07C67/00
Domestic Patent References:
| WO2021155257A1 | 2021-08-05 |
Foreign References:
| CN112707795A | 2021-04-27 |
Other References:
YANG, S. J. ET AL.: "DITERPENES FROM TAXUS MAIREI", PHYTOCHEMISTRY, vol. 49, no. 7, 31 December 1998 (1998-12-31), XP004290313, DOI: 10.1016/S0031-9422(98)00443-9
WANG XUE CHAO, ZHANG CHI, PAN XIN-FU, CHEN YAO-ZU : "Studies on the Total Synthesis of Taxamairin B", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, vol. 16, no. 6, 30 June 1995 (1995-06-30), pages 913 - 914, XP093104798
THOMMEN, C. ET AL.: "Collective Syntheses of Icetexane Nature Products Based on Biogenetic Hypotheses", CHEM. EUR. J., vol. 23, 29 November 2016 (2016-11-29), XP071842716, DOI: 10.1002/chem.201603932
CAO WEI, LIU TINGTING, YANG SHUTING, LIU MOUDE, PAN ZHENGHONG, ZHOU YINGJUN, DENG XU: "Efficient Synthesis of Icetexane Diterpenes and Apoptosis Inducing Effect by Upregulating BiP-ATF4-CHOP Axis in Colorectal Cells", JOURNAL OF NATURAL PRODUCTS, AMERICAN CHEMICAL SOCIETY, US, vol. 84, no. 7, 23 July 2021 (2021-07-23), US , pages 2012 - 2019, XP093104796, ISSN: 0163-3864, DOI: 10.1021/acs.jnatprod.1c00310
MAJETICH GEORGE, LI YANG, ZOU GE: "Total Synthesis of (±)-Komaroviquinone", HETEROCYCLES, JAPAN INSTITUTE OF HETEROCYCLIC CHEMISTRY, JP, vol. 73, no. 1, 1 January 2007 (2007-01-01), JP , pages 217 - 225, XP009550032, ISSN: 0385-5414, DOI: 10.3987/COM-07-S(U)36
WANG XUE CHAO, ZHANG CHI, PAN XIN-FU, CHEN YAO-ZU : "Studies on the Total Synthesis of Taxamairin B", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, vol. 16, no. 6, 30 June 1995 (1995-06-30), pages 913 - 914, XP093104798
THOMMEN, C. ET AL.: "Collective Syntheses of Icetexane Nature Products Based on Biogenetic Hypotheses", CHEM. EUR. J., vol. 23, 29 November 2016 (2016-11-29), XP071842716, DOI: 10.1002/chem.201603932
CAO WEI, LIU TINGTING, YANG SHUTING, LIU MOUDE, PAN ZHENGHONG, ZHOU YINGJUN, DENG XU: "Efficient Synthesis of Icetexane Diterpenes and Apoptosis Inducing Effect by Upregulating BiP-ATF4-CHOP Axis in Colorectal Cells", JOURNAL OF NATURAL PRODUCTS, AMERICAN CHEMICAL SOCIETY, US, vol. 84, no. 7, 23 July 2021 (2021-07-23), US , pages 2012 - 2019, XP093104796, ISSN: 0163-3864, DOI: 10.1021/acs.jnatprod.1c00310
MAJETICH GEORGE, LI YANG, ZOU GE: "Total Synthesis of (±)-Komaroviquinone", HETEROCYCLES, JAPAN INSTITUTE OF HETEROCYCLIC CHEMISTRY, JP, vol. 73, no. 1, 1 January 2007 (2007-01-01), JP , pages 217 - 225, XP009550032, ISSN: 0385-5414, DOI: 10.3987/COM-07-S(U)36
Attorney, Agent or Firm:
BEIJING PAT SF INTELLECTUAL PROPERTY AGENCY CO. LTD (CN)
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