(3,4-methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine | 39989-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (3,4-methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine
• 英文别名: 1-(1,3-benzodioxol-5-yl)-N-(2,2-dimethoxyethyl)methanimine
• CAS: 39989-38-3
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: BDXJXDXQNDFZBE-UHFFFAOYSA-N

物化性质

• 沸点：
  147 °C(Press: 0.4 Torr)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,4-methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine 在 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 7,8,9-Trimethoxy-2,3-methylenedioxy-11H-indeno[1,2-c]isoquinoline Hydrochloride
  参考文献：
  名称：

  Synthesis of Indenoisoquinoliniums and Methods of Use

  摘要：

  描述了取代的茚喹啉化合物，以及取代的茚喹啉化合物的制药配方。还描述了制备取代的茚喹啉化合物的方法。还描述了使用所述的取代的茚喹啉化合物或其制药配方来治疗哺乳动物癌症的方法。

  公开号：

  US20080242692A1
• 作为产物：
  描述：

  胡椒醛 、 氨基乙醛缩二甲醇 以 甲苯 为溶剂， 生成 (3,4-methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine
  参考文献：
  名称：

  一种有效的Ugi-3CR /氮杂Diels–Alder / Pomeranz–Fritsch方案，用于（±）-新戊胺，（±）-lennoxamine和麦格丙胺的新型氮杂类似物：面向多样性的合成方法†

  摘要：

  描述了一系列（±）-新胺，（±）-伦诺明和麦加丙氨酸氮杂类似物的快速有效合成。合成策略涉及Ugi-3CR和另外两个缩合过程，即aza-Diels-Alder环加成反应和Pomeranz-Fritsch反应。醛基部分链大小的变化仅在两个操作反应步骤中提供了结构多样性。

  DOI：

  10.1039/c6ob02572b

文献信息

• Synthesis of indenoisoquinoliniums and methods of use
  申请人：Purdue Research Foundation

  公开号：US07781445B2

  公开（公告）日：2010-08-24

  Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for treating cancer in mammals using the described substituted indenoisoquinolinium compounds or pharmaceutical formulations thereof.

  本文介绍了替代的吲哚异喹啉化合物以及替代的吲哚异喹啉化合物的药物配方。还介绍了制备替代吲哚异喹啉化合物的方法。同时，本文还介绍了使用所述的替代吲哚异喹啉化合物或其药物配方治疗哺乳动物癌症的方法。
• Synthesis and Mechanism of Action Studies of a Series of Norindenoisoquinoline Topoisomerase I Poisons Reveal an Inhibitor with a Flipped Orientation in the Ternary DNA−Enzyme−Inhibitor Complex As Determined by X-ray Crystallographic Analysis
  作者：Alexandra Ioanoviciu、Smitha Antony、Yves Pommier、Bart L. Staker、Lance Stewart、Mark Cushman

  DOI：10.1021/jm050076b

  日期：2005.7.1

  Several norindenoisoquinolines substituted with methoxy or methylenedioxy groups have been prepared and their anticancer properties evaluated in cancer cell cultures and in topoisomerase I inhibition assays. 2,3-Dimethoxy-8,9-methylenedioxy-11H-indeno[1,2-c]isoquinoline hydrochloride (14) is a strong topoisomerase I inhibitor and also displays very high cytotoxicity in the NCI cancer cell culture screen (mean graph midpoint of 50 nM). The X-ray crystal structure of norindenoisoquinoline 14 in complex with topoisomerase I and DNA has been solved, providing insight into the structure-activity relationships within this class of new anticancer agents. The number and position of the norindenoisoquinoline substituents have a significant influence on biological activity and demonstrate that substitution on the nitrogen atom is not an absolute requirement for the antitumor effect of the indenoisoquinolines. Removal of the 11-keto group from the lead compound 1 and replacement of the N-alkyllactam with an unsubstituted pyridine ring causes the indenoisoquinoline ring system to flip over in the DNA-enzyme-inhibitor ternary complex. This allows the nitrogen atom to assume the hydrogen bond acceptor role of the 11-keto group, resulting in hydrogen bonding to Arg364.
• An efficient Ugi-3CR/aza Diels–Alder/Pomeranz–Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach
  作者：Óscar Vázquez-Vera、Jorge S. Sánchez-Badillo、Alejandro Islas-Jácome、Manuel A. Rentería-Gómez、Shrikant G. Pharande、Carlos J. Cortes-García、Mónica A. Rincón-Guevara、Ilich A. Ibarra、Rocío Gámez-Montaño、Eduardo González-Zamora

  DOI：10.1039/c6ob02572b

  日期：——

  rapid and efficient synthesis of a series of (±)-nuevamine, (±)-lennoxamine and magallanesine aza analogues is described. The synthetic strategy involves Ugi-3CR and two further condensation processes, aza-Diels–Alder cycloaddition and the Pomeranz–Fritsch reaction. The variation of the chain-size in aldehyde moieties provided structural diversity in only two operational reaction steps.

  描述了一系列（±）-新胺，（±）-伦诺明和麦加丙氨酸氮杂类似物的快速有效合成。合成策略涉及Ugi-3CR和另外两个缩合过程，即aza-Diels-Alder环加成反应和Pomeranz-Fritsch反应。醛基部分链大小的变化仅在两个操作反应步骤中提供了结构多样性。
• Synthesis of Indenoisoquinoliniums and Methods of Use
  申请人：Cushman Mark S.

  公开号：US20080242692A1

  公开（公告）日：2008-10-02

  Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for treating cancer in mammals using the described substituted indenoisoquinolinium compounds or pharmaceutical formulations thereof.

  描述了取代的茚喹啉化合物，以及取代的茚喹啉化合物的制药配方。还描述了制备取代的茚喹啉化合物的方法。还描述了使用所述的取代的茚喹啉化合物或其制药配方来治疗哺乳动物癌症的方法。