15-deoxymatrine | 478-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 15-deoxymatrine
• 英文别名: (7a)-(7ar,13at,13bc,13cc)-dodecahydro-dipyrido[2,1-f;3',2',1'-ij][1,6]naphthyridine；Matridin；matridine；(1R,2R,9S,17S)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecane
• CAS: 478-81-9；569-24-4；6475-08-7；6838-35-3；6882-67-3；17844-90-5；26252-03-9；53776-48-0；53798-49-5；54383-33-4
• 化学式: C₁₅H₂₆N₂
• 分子量: 234.385
• InChiKey: UENROKUHQFYYJA-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  15-deoxymatrine 在 双氧水 作用下， 反应 0.5h， 以68%的产率得到1,16-dioxo-15-deoxymatrine
  参考文献：
  名称：

  苦参碱衍生物及其制备方法和在农药上的应 用

  摘要：

  本发明涉及苦参碱衍生物(I)及其制备方法和在防治植物病毒、杀虫、杀菌方面的应用，式中各基团的意义见说明书。本发明的苦参碱衍生物表现出特别优异的抗植物病毒活性，还具有杀菌活性和杀虫活性。

  公开号：

  CN105884775B
• 作为产物：
  描述：

  苦参碱 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 15-deoxymatrine
  参考文献：
  名称：

  一种简单的苦参碱衍生物，可轻松合成中孔沸石ITQ-37和ITQ-43 †

  摘要：

  具有介孔结构的ITQ-37和ITQ-43由于涉及大分子的前景广阔的应用而引起了人们的极大兴趣。然而，合成这些沸石是具有挑战性的。在此，已经通过使用简单的苦参碱衍生的有机结构导向剂合成了具有1.7和3.0的增强的Si / Ge比的MAS-ITQ-37和MAS-ITQ-43。

  DOI：

  10.1039/c8cc08196d

文献信息

• Total Synthesis of Matrine Alkaloids
  作者：Nicholas L. Magann、Erin Westley、Madison J. Sowden、Michael G. Gardiner、Michael S. Sherburn

  DOI：10.1021/jacs.2c09804

  日期：2022.11.2

  The total synthesis of three diastereomeric matrine natural products is reported. The 8-step synthesis commences with simple acyclic precursors, forms all 4 rings of the tetracyclic natural product framework, and forges 10 of the 20 covalent bonds of the target structure. A cross-conjugated triene is positioned at the core of an acyclic branched structure. This precursor collapses to the tetracyclic

  报道了三种非对映苦参碱天然产物的全合成。8 步合成从简单的无环前体开始，形成四环天然产物框架的所有 4 个环，并形成目标结构 20 个共价键中的 10 个。交叉共轭三烯位于无环支化结构的核心。该前体通过两个独立的分子内环加成的精心安排的序列折叠成四环天然产物框架。随后的后期氢化伴随着应变释放氧化还原差向异构化以提供三种天然产物。以同样的方式制备了前所未有的卡巴类似物。苦参碱的半合成操作提供了获得 10 种额外天然产物的途径。
• Synthesis, characterization and in vitro anti-tumor activities of matrine derivatives
  作者：Lisheng Wang、Yejun You、Songqing Wang、Xu Liu、Buming Liu、Jinni Wang、Xiao Lin、Mingsheng Chen、Gang Liang、Hua Yang

  DOI：10.1016/j.bmcl.2012.04.069

  日期：2012.6

  Nineteen previously unreported matrine derivatives were synthesized and characterized using elemental analysis, infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and mass spectrometry. Target compounds 6a-6l and 7a-7c showed stronger inhibitory activities than matrine in the in vitro antitumor tests and inhibited the growth of the Hep7402, B16-F10, A549, and TW03 cell lines. In addition, compound 6i exhibited a potent antitumor activity similar to that of colchicine. (C) 2012 Elsevier Ltd. All rights reserved.
• Various Bioactivity and Relationship of Structure–Activity of Matrine Analogues
  作者：Wanjun Ni、Chaojie Li、Yuxiu Liu、Hongjian Song、Lizhong Wang、Haibin Song、Qingmin Wang

  DOI：10.1021/acs.jafc.6b05474

  日期：2017.3.15

  For the first time, the botanic source natural product matrine was reported to have more potent inhibitory activity against tobacco mosaic virus (TMV) than the commercial virucide ribavirin. On the basis of the structural diversity modification strategy, a series of matrine derivatives was synthesized and systematically evaluated for their antiviral activity against TMV, fungicidal activity, and insecticidal activity. As a result, compounds 3 (inhibitory rate 67.3%, 69.5%, 63.7%, 63.0% at 500 mu g/mL for in vitro activity, inactivation, curative, and protection activities in vivo, respectively), 16 (66.7%, 60.7%, 63.8%, 68.9% at 500 mu g/mL), and 32 (74.6%, 76.9%, 72.3%, 75.7% at 500 mu g/mL) were found to have much higher anti-TMV activity than ribavirin (40.8%, 37.5%, 38.2%, 37.7% at 500 mu g/mL), even exhibiting as well as NK-007 (70.3%, 66.1%, 68.4%, 67.5% at 500 mu g/mL), which was an efficient compound created by our group previously. At the same time, it was found that matrine and its derivatives had a broad spectrum fungicidal activity (14 fungi), especially the inhibition of compound 32 against Phytophthora capsici Leonian reached 96.4% at a concentration of 50,mu g/mL. What's more, all compounds exhibited very good insecticidal activity to five kinds of insects (including Mythimna Separate, Helicoverpa Armigera, Ostrinia Nubilalis, Plutella xylostella, and Culex Pipiens Pallens); especially, the inhibition rate of C. Pipiens Pallens of compound 22 could still reach 70% at 1,mu g/mL.
• Studies on the Synthesis of Matrine. II. The Synthesis of Octadehydromatrine and Allomatridine¹
  作者：KYOSUKE TSUDA、HIROSHI MISHIMA

  DOI：10.1021/jo01102a026

  日期：1958.8
• Ochiai; Minato, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 914,917
  作者：Ochiai、Minato

  DOI：——

  日期：——