6-Methoxy-3-[2-{tert-butoxycarbonyl}amino)ethyl]-1-(p-toluenesulfonyl)indole-4,7-dione | 161156-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Methoxy-3-[2-{tert-butoxycarbonyl}amino)ethyl]-1-(p-toluenesulfonyl)indole-4,7-dione
• 英文别名: tert-butyl N-[2-[6-methoxy-1-(4-methylphenyl)sulfonyl-4,7-dioxoindol-3-yl]ethyl]carbamate
• CAS: 161156-09-8
• 化学式: C₂₃H₂₆N₂O₇S
• 分子量: 474.535
• InChiKey: LEIQQYAWCBDUTR-UHFFFAOYSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-Methoxy-3-[2-{tert-butoxycarbonyl}amino)ethyl]-1-(p-toluenesulfonyl)indole-4,7-dione 在 氧气 、 sodium methylate 、 碳酸氢钠 、 三乙胺 、 三氟乙酸 、 copper dichloride 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 discorhabdin C
  参考文献：
  名称：

  Discorhabdin生物碱的仿生方法：Discorhabdins C和E和Dethiadiscorhabdin D的总合成。

  摘要：

  Discorhabdin生物碱的特征性螺二烯酮结构很容易通过酪胺取代的吲哚喹啉亚胺26、35和36与氯化铜，三乙胺和氧的反应而形成。这种环化提供了一种可能的仿生途径，可以合成Discorhabdins C和E（41和42）。未溴化的螺二烯酮40在Pd / C上与氢反应生成烯酮46。在α位置的溴化反应得到溴烯酮的混合物，在用碱性氧化铝处理后，该溴烯酮会平滑转化为去噻二氢腐霉菌素D（4）。

  DOI：

  10.1021/jo9815397
• 作为产物：
  描述：

  tert-butyl (2-(7-(benzyloxy)-6-methoxy-1H-indol-3-yl)ethyl)carbamate 在 palladium on activated charcoal potassium nitrososulfonate 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 6-Methoxy-3-[2-{tert-butoxycarbonyl}amino)ethyl]-1-(p-toluenesulfonyl)indole-4,7-dione
  参考文献：
  名称：

  Discorhabdin生物碱的仿生方法：Discorhabdins C和E和Dethiadiscorhabdin D的总合成。

  摘要：

  Discorhabdin生物碱的特征性螺二烯酮结构很容易通过酪胺取代的吲哚喹啉亚胺26、35和36与氯化铜，三乙胺和氧的反应而形成。这种环化提供了一种可能的仿生途径，可以合成Discorhabdins C和E（41和42）。未溴化的螺二烯酮40在Pd / C上与氢反应生成烯酮46。在α位置的溴化反应得到溴烯酮的混合物，在用碱性氧化铝处理后，该溴烯酮会平滑转化为去噻二氢腐霉菌素D（4）。

  DOI：

  10.1021/jo9815397

文献信息

• Azide-Mediated Detosylation of <i>N</i>-Tosylpyrroloiminoquinones and <i>N</i>-Tosylindole-4,7-quinones
  作者：Sadanandan Velu、Swayamprabha Patel、Dwayaja Nadkarni、Srinivasan Murugesan、Jason King

  DOI：10.1055/s-0028-1083570

  日期：——

  The utility of NaN3 as a reagent for the detosylation of N-tosylpyrroloiminoquinones and N-tosylindole-4,7-quinones is described. The NaN3-mediated detosylation is carried out in polar aprotic solvents such as DMF and DMSO. The reaction occurs under neutral, mild conditions and results in good to excellent yields of the detosylated quinones.

  NaN3作为N-甲苯磺酰吡咯并咪诺喹啉和N-甲苯磺酰吲哚-4,7-喹啉脱甲苯磺酰化反应试剂的实用性已经得到了描述。在极性质子惰性溶剂如DMF和DMSO中进行NaN3介导的脱甲苯磺酰化反应。该反应在温和中性条件下进行，并能获得较好的至优异的脱甲苯磺酰化喹啉产率。
• A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase Inhibitors
  作者：Rachana V. Ohri、Alexander T. Radosevich、K. James Hrovat、Christine Musich、David Huang、Theodore R. Holman、F. Dean Toste

  DOI：10.1021/ol050897a

  日期：2005.6.1

  A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.
• Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach
  作者：Eyyani V. Sadanandan、Sasi K. Pillai、M. V. Lakshmikantham、Adil D. Billimoria、J. Shane Culpepper、Michael P. Cava

  DOI：10.1021/jo00111a043

  日期：1995.3

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).
• Total synthesis of zyzzyanones A–D
  作者：Dwayaja H. Nadkarni、Srinivasan Murugesan、Sadanandan E. Velu

  DOI：10.1016/j.tet.2013.03.052

  日期：2013.5

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.
• Marine Alkalod Makaluvamines and Derivatives Thereof
  申请人：Velu Sadanandan E.

  公开号：US20100144779A1

  公开（公告）日：2010-06-10

  The present disclosure provides compounds based on the marine alkaloid makaluvamine. Described are compounds of the general formula (I) and (II). Also described are pharmaceutical compositions comprising one or more of the compounds of the general formula (I) and (II). The compounds and pharmaceutical compositions described inhibit the growth of several cancer lines, induce apoptosis and cell cycle arrest, display topoisomerase II inhibitory activity and modulate the activity and/or expression of key proteins involved in the regulation of cell growth. Methods of treatment and prevention using the compounds and pharmaceutical compositions described are also provided.