Title:
PREPARATION METHOD FOR NATURAL BUFOGENIN COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/151623
Kind Code:
A1
Abstract:
A preparation method for a natural bufogenin compound, comprising: taking cheap and easily available commercial steroid skeleton materials such as androstenedione 4-AD or 3β-hydroxyl-5β-androstane-17-ketone; performing simple conversion by means of a biological-chemical relay synthesis or chemical synthesis method to obtain an intermediate 3β,14α-dihydroxyl-5β-androsterane-17-ketone compound; then completing uploading of an E ring, namely a hexaenolactone ring by means of chemical semi-synthesis; and finally realizing synthesis of the bufogenin compound. The preparation method is simple to operate and high in yield, can be used for large-scale preparation of the natural products, and has a wide application prospect.
Inventors:
LIN GUOQIANG (CN)
YE WENBO (CN)
ZHAO QUNFEI (CN)
ZHANG JIANGE (CN)
HE QINGLI (CN)
WANG CHAO (CN)
YE WENBO (CN)
ZHAO QUNFEI (CN)
ZHANG JIANGE (CN)
HE QINGLI (CN)
WANG CHAO (CN)
Application Number:
PCT/CN2023/075214
Publication Date:
August 17, 2023
Filing Date:
February 09, 2023
Export Citation:
Assignee:
UNIV SHANGHAI TRADITIONAL CHINESE MEDICINE (CN)
International Classes:
C07J1/00; C07J71/00
Domestic Patent References:
| WO2006120472A2 | 2006-11-16 |
Foreign References:
| US3687944A | 1972-08-29 | |||
| CN114395011A | 2022-04-26 |
Other References:
SONDHEIMER FRANZ, W. MCCRAE AND W. G. SALMOND: "Synthesis of bufadienolides. Synthesis of bufalin and resibufogenin", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 91, no. 5, 26 February 1969 (1969-02-26), pages 1228 - 1230, XP093083612, ISSN: 0002-7863, DOI: 10.1021/ja01033a039
PETTIT GEORGE R, AM ANO YOSHIAKI K, BRUSCHWEILER FRED, BROWN PETER: "Steroids and related natural products. 67. Bufadienolides. 14. Synthesis of bufotalien, 15.alpha.-hydroxybufalin, and resibufogenin", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 36, no. 24, 24 December 1971 (1971-12-24), pages 3736 - 3739, XP093083613, ISSN: 0022-3263, DOI: 10.1021/jo00823a016
SHIMIZU SHINSUKE, HAGIWARA KOICHI, ITOH HIROAKI, INOUE MASAYUKI: "Unified Total Synthesis of Five Bufadienolides", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 21, 6 November 2020 (2020-11-06), US , pages 8652 - 8657, XP093083614, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c03251
FERLAND J. M., LEFEBVRE Y.: "Synthetic cardenolides and related products. IV. D -homo derivatives", CANADIAN JOURNAL OF CHEMISTRY, NRC RESEARCH PRESS, CA, vol. 62, no. 2, 1 February 1984 (1984-02-01), CA , pages 309 - 314, XP093083615, ISSN: 0008-4042, DOI: 10.1139/v84-054
PETTIT GEORGE R, AM ANO YOSHIAKI K, BRUSCHWEILER FRED, BROWN PETER: "Steroids and related natural products. 67. Bufadienolides. 14. Synthesis of bufotalien, 15.alpha.-hydroxybufalin, and resibufogenin", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 36, no. 24, 24 December 1971 (1971-12-24), pages 3736 - 3739, XP093083613, ISSN: 0022-3263, DOI: 10.1021/jo00823a016
SHIMIZU SHINSUKE, HAGIWARA KOICHI, ITOH HIROAKI, INOUE MASAYUKI: "Unified Total Synthesis of Five Bufadienolides", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 21, 6 November 2020 (2020-11-06), US , pages 8652 - 8657, XP093083614, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c03251
FERLAND J. M., LEFEBVRE Y.: "Synthetic cardenolides and related products. IV. D -homo derivatives", CANADIAN JOURNAL OF CHEMISTRY, NRC RESEARCH PRESS, CA, vol. 62, no. 2, 1 February 1984 (1984-02-01), CA , pages 309 - 314, XP093083615, ISSN: 0008-4042, DOI: 10.1139/v84-054
Attorney, Agent or Firm:
XU & PARTNERS , LLC. et al. (CN)
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