铁屎米酮N氧化物 | 60755-87-5

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 中文名称: 铁屎米酮N氧化物
• 中文别名: 铁屎米酮N氧化物
• 英文名称: canthin-6-one-3-N-oxide
• 英文别名: canthin-6-one N-oxide；6-oxido-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-6-ium-2-one
• CAS: 60755-87-5
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: PMKULNRVYULJPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3,3a,4,5-六氢铁屎米酮 在 5%-palladium/activated carbon 、 间氯过氧苯甲酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 铁屎米酮N氧化物
  参考文献：
  名称：

  Synthesis, in vitro antibacterial activities of a series of 3- N -substituted canthin-6-ones

  摘要：

  An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (mu g.mL(-1)) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (mu g.mL(-1)) against Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.070

文献信息

• Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin-6-one β-Carboline Series and Study of Phenotypic Properties on<i>C. elegans</i>
  作者：Gerardo Cebrián-Torrejón、Nicolas Mackiewicz、Rafael P. Vázquez-Manrique、Alain Fournet、Bruno Figadère、Julien Nicolas、Erwan Poupon

  DOI：10.1002/ejoc.201300770

  日期：2013.9

  Based on the biosynthetic line of canthin-6-one alkaloids from their simple precursors such as tryptamine, the present work is focused on the study of alternative protocol of the Bischler-Napieralski reaction and has led to a full coverage of the different biosynthetic intermediates. Nanoparticles were also prepared as mimics of biosynthetic assembly lines and some interesting biological results in

  基于来自色胺等简单前体的角蛋白-6-一生物碱的生物合成线，目前的工作重点是研究 Bischler-Napieralski 反应的替代方案，并全面覆盖了不同的生物合成中间体。纳米颗粒也被制备为生物合成装配线的模拟物，并且还报道了一些有趣的化学生态学生物学结果。
• USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended
  申请人：Fournet Alain Robert Francois Maxime

  公开号：US20110059977A1

  公开（公告）日：2011-03-10

  The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.

  本发明涉及使用以下式(I)中至少一种化合物，用于制备用于治疗或预防与分支杆菌相关或由其引起的病理状况的药物，其中B特别代表氮原子，而R1、R2、R3、R4、R5、R6、R7和R8特别代表氢原子。
• Haynes et al., Australian Journal of Scientific Research, Series A: Physical Sciences, 1952, vol. <A> 5, p. 387,398
  作者：Haynes et al.

  DOI：——

  日期：——
• Extraction, Hemisynthesis, and Synthesis of Canthin-6-one Analogues. Evaluation of Their Antifungal Activities
  作者：Flor Soriano-Agatón、Delphine Lagoutte、Erwan Poupon、François Roblot、Alain Fournet、Jean-Charles Gantier、Reynald Hocquemiller

  DOI：10.1021/np050250z

  日期：2005.11.1

  Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities.
• UTILISATION DE LA CANTHIN-6-ONE ET SES ANALOGUES DANS LE TRAITEMENT DES PATHOLOGIES LIEES AUX MYCOBACTERIES
  申请人：Institut de Recherche pour le Développement

  公开号：EP1998770B1

  公开（公告）日：2010-04-21