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ZHAO Zeng, XU Xusheng, SUN Qingyan, CHEN Hao, LIU Runhui. Configuration inversion of C-2-hydroxy in lycorine[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(6): 511-515. doi: 10.3969/j.issn.1006-0111.2016.06.008
Citation: ZHAO Zeng, XU Xusheng, SUN Qingyan, CHEN Hao, LIU Runhui. Configuration inversion of C-2-hydroxy in lycorine[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(6): 511-515. doi: 10.3969/j.issn.1006-0111.2016.06.008

Configuration inversion of C-2-hydroxy in lycorine

doi: 10.3969/j.issn.1006-0111.2016.06.008
  • Received Date: 2016-04-16
  • Rev Recd Date: 2016-06-21
  • Objective Study configuration inversion of C-2-hydroxy in lycorine to provide a foundation for semi-synthesis of asiaticumine B. Methods Use instrumental analyses to explore the C-2-hydroxy configuration through oxidation and reduction reactions. Results Accomplished configuration inversion of C-2-hydroxy in lycorine with 49% yield. Conclusion We identified a convenient and efficient method for the configuration inversion of C 2-hydroxy in lycorine.
  • [1] Lamoral-Theys D, Andolfi A, Van Goietsenoven G. et al. Lycorine,the main phenanthridine amaryllidaceae alkaloid,exhibits significant antitumor activity in cancer cells that display resistance toproapoptotic stimuli:an investigation of structure-activity relationship and mechanistic insight[J]. J Med Chem, 2009,52(20):6244-6256.
    [2] Liu J, Yang Y, Xu Y,et al. Lycorine reduces mortality of human enterovirus 71-infected mice by inhibiting virus replication[J]. Virol J,2011,8:483.
    [3] 抗晶晶, 王辉. 石蒜碱抗炎作用研究进展[J].中国野生植物资源,2013, 32(6):1-3.
    [4] 秦昆明, 李笑, 徐昭,等. 石蒜碱及其衍生物的药理作用研究概况[J].北京联合大学学报(自然科学版),2009, 23(1):6-10.
    [5] 孙倩. 文殊兰化学成分及生物活性研究[D].上海:第二军医大学, 2008.
    [6] Clevers H, Nusse R. Wnt/β-catenin signaling and disease[J]. Cell, 2012,149(6):1192-1205.
    [7] Wang P,Li LF,Wang QY,et al. Anti-dengue-virus activity and structure-activity relationship studies of lycorine derivatives[J]. Chem Med Chem,2014,9(7):1522-1533.
    [8] Schultz AG, Holoboski MA, Smyth MS. The first asymmetric total syntheses of (+)-lycorine and (+)-1-deoxylycorine[J]. J Am Chem Soc, 1996,118(26):6210-6219.
    [9] Evdokimov NM, Lamoral-theys D,Mathieu V,et al. In search of a cytostatic agent derived from the alkaloid lycorine:synthesis and growth inhibitory properties of lycorine derivatives[J]. Bioorgan Med Chem, 2011, 19(23):7252-7261.
    [10] Kurti L,Czakó B. Strategic applications of named reactions in organic synthesis[M].Elsevier:Academic Press, 2005.
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Configuration inversion of C-2-hydroxy in lycorine

doi: 10.3969/j.issn.1006-0111.2016.06.008

Abstract: Objective Study configuration inversion of C-2-hydroxy in lycorine to provide a foundation for semi-synthesis of asiaticumine B. Methods Use instrumental analyses to explore the C-2-hydroxy configuration through oxidation and reduction reactions. Results Accomplished configuration inversion of C-2-hydroxy in lycorine with 49% yield. Conclusion We identified a convenient and efficient method for the configuration inversion of C 2-hydroxy in lycorine.

ZHAO Zeng, XU Xusheng, SUN Qingyan, CHEN Hao, LIU Runhui. Configuration inversion of C-2-hydroxy in lycorine[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(6): 511-515. doi: 10.3969/j.issn.1006-0111.2016.06.008
Citation: ZHAO Zeng, XU Xusheng, SUN Qingyan, CHEN Hao, LIU Runhui. Configuration inversion of C-2-hydroxy in lycorine[J]. Journal of Pharmaceutical Practice and Service, 2016, 34(6): 511-515. doi: 10.3969/j.issn.1006-0111.2016.06.008
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