CAS: 639-43-0; Akuammicine

该化合物是一种主要源于以传统药用著而闻名的非洲沃阿坎加植物的种子的杂醇藻类,其特点是结构复杂,其特点是具有双环框架,在其环中含有氮原子;氨基氨基氨基氨存在一系列生物活动,包括止痛,抗炎和潜在的抗疟影响,这使药物研究感兴趣;该化合物与各种...

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    3-(Tert-Butyl) 6-Methyl 1,2,3A,4,6A,7-Hexahydro-3H-Pyrrolo[2,3-D]Carbazole-3,6-Dicarboxylate
    Methyl (3As,6Ar,11Br)-2,3,3A,4,6A,7-Hexahydro-1H-Pyrrolo[2,3-D]Carbazole-6-Carboxylate 1322613-98-8
    (+/-)-Dehydrotubifoline
    (+/-)-(1R*,7R*,8S*)-2-(E)-Ethylidene-7-<2-<5-(1,3-Dimethylhexahydro-2-Oxo-1,3,5-Triazine)>Phenyl>-4-Azatricyclo<5.2.2.04,8>Undecan-11-One
    (1Rs,7Rs,8Sr)-7-(2-Nitrophenyl)-2-Vinylidene-4-Azatricyclo[5.2.2.04,8]Undecan-11-One
    1-Chloroethyl (3Ar,7As)-3A-(2-Nitrophenyl)-4-Oxo-2,3,7,7A-Tetrahydroindole-1-Carboxylate
    16-Decarbomethoxy-21-Oxotetrahydroalstonine
    (3Ar,7As)-3A-(2-Nitrophenyl)-1-(4-Trimethylsilylbut-2-Ynyl)-2,3,7,7A-Tetrahydroindol-4-One 192431-40-6
    1-Chloroethyl (3Ar,7As)-3A-(2-Nitrophenyl)-4-Oxo-2,3,5,6,7,7A-Hexahydroindole-1-Carboxylate
    (+/-)-(19α,20α)-19-Methyloxayohimban-17,21-Dione

    合成工艺路线路线简述

      📜Methyl (3As,6Ar,11Br)-2,3,3A,4,6A,7-Hexahydro-1H-Pyrrolo[2,3-D]Carbazole-6-Carboxylate置于palladium Diacetate,三乙胺,N,N-二异丙基乙胺,三苯基膦体系中,用 乙腈 作为反应溶剂,化学反应 5.0H,反应生成 (19E)-2,16,19,20-四去氢枯苒-17-酸甲酯
      参考文献:通过区域和立体控制的合作催化下的马钱子和白屈菜碱生物碱的对映选择性合成.
      标题:通过区域和立体控制的合作催化下的马钱子和白屈菜碱生物碱的对映选择性合成.
      摘要:我们描述的对映选择性合成马钱子和白屈菜生物碱.在第一种情况下,吲哚乙酸酯被确定为对映选择性协同异硫脲/ Pd催化α-烷基化的优秀伴侣亲核试剂.这提供了以高收率和出色的对映体诱导水平包含吲哚的立构中心的产品,其方式明显独立于n取代基.这导致了(−)‐ Akuammicine和(−)‐ Strychnine的简明合成.在第二种情况下,邻位表现不佳对映选择性协同异硫脲/ Ir催化的α-烷基化反应中的预取代肉桂酸亲电试剂可通过适当的取代基选择来克服,从而导致(+)-螯合碱,(+)-去甲螯合碱和(+)-螯合胺的对映选择性合成.
      DOI:10.1002/anie.202005151

      海关参考信息

      专利信息


      专利号:US-12435094-B1
      优先权日:2024-11-12
      标题:Methods of preparing isomers, analogs, and synthetic derivatives from akuamma seeds
      发明人:MITCHELL HAYWOOD MAX; PAGE CECIL; MERINO JOSEPH WILLIAM
      权利人:MITCHELL HAYWOOD MAX; PAGE CECIL; MERINO JOSEPH WILLIAM
      摘要:Methods are provided for the extraction, isolation, and synthesis of akuammine and other naturally occurring alkaloids from the seeds of the plant Picralima nitida (Akuamma), and their conversion to a variety of isomers, analogs, and synthetic derivatives.

      专利号:US-11072613-B2
      优先权日:2016-03-02
      标 题:Compositions and methods for making terpenoid indole alkaloids
      发明人:DE LUCA VINCENZO; QU YANG
      权利人:WILLOW BIOSCIENCES INC
      摘要:Methods that may be used for the manufacture of a class of chemical compounds known as terpenoid indole alkaloids, including tabersonine and catharanthine are provided. Compositions useful for the synthesis of terpenoid indole alkaloids, including tabersonine and catharanthine are also provided. The provided compounds are useful in the manufacture of chemotherapeutic agents.

      供应商参考报价(招募中)

      品牌试剂参考报价(招募中)

      📌 第三方产品分析报告

      ✅ COA系统入驻 | 共享模式

      主要参考文献


      1: Tatsis EC, Carqueijeiro I, Dugé de Bernonville T, Franke J, Dang TT, Oudin A, Lanoue A, Lafontaine F, Stavrinides AK, Clastre M, Courdavault V, O'Connor SE. A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate. Nat Commun. 2017 Aug 22;8(1):316. doi: 10.1038/s41467-017-00154-x.
      2: Munagala S, Sirasani G, Kokkonda P, Phadke M, Krynetskaia N, Lu P, Sharom FJ, Chaudhury S, Abdulhameed MD, Tawa G, Wallqvist A, Martinez R, Childers W, Abou-Gharbia M, Krynetskiy E, Andrade RB. Synthesis and evaluation of Strychnos alkaloids as MDR reversal agents for cancer cell eradication. Bioorg Med Chem. 2014 Feb 1;22(3):1148-55. doi: 10.1016/j.bmc.2013.12.022. Epub 2013 Dec 21.

      合成参考文献


      参考文献:10.1038/nature10232
      摘要:Jones SB, Simmons B, Mastracchio A, MacMillan DW. Collective synthesis of natural products by means of organocascade catalysis. Nature. 2011 Jul 13;475(7355):183–8.
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