1-(1,3-benzodioxol-5-yl)-N-ethylmethanimine | 80985-00-8

• 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: 1-(1,3-benzodioxol-5-yl)-N-ethylmethanimine
• 英文别名: piperonal-ethylimine；Piperonal-aethylimin；3,4-Methylenedioxybenzylideneethylamine
• CAS: 80985-00-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: VCXCEVVTIMSXQD-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(1,3-benzodioxol-5-yl)-N-ethylmethanimine 在 氯化亚砜 、 四磷十氧化物 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 cis-6-ethyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Novel Oxidative Transformation of Indenoisoquinolines to Isoquinoline-3-spiro-3‘-phthalides in the Presence of Osmium Tetraoxide and 4-Methylmorpholine N-Oxide

  摘要：

  DOI：

  10.1021/jo980928y
• 作为产物：
  描述：

  胡椒醛 、 乙胺 以93%的产率得到1-(1,3-benzodioxol-5-yl)-N-ethylmethanimine
  参考文献：
  名称：

  Indenoisoquinolines as antineoplastic agents

  摘要：

  已完成。已准备和评估了多种吲哚异喹啉类化合物在人类癌细胞培养物中的细胞毒性和对拓扑异构酶I的活性。其中两种最具细胞毒性的吲哚异喹啉被证明是顺式-6-乙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-(亚甲二氧基)-5,11-二氧基-11H-吲哚[1,2-c]异喹啉和顺式-6-烯丙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-(亚甲二氧基)-5,11-二氧基-(11H)吲哚[1,2-c]异喹啉。其中两种最有效的拓扑异构酶I抑制剂分别是6-(3-羧基-1-丙基)-5,6-二氢-5,11-二氧基-11H-吲哚[1,2-c]异喹啉 (26) 和6-乙基-2,3-二甲氧基-8,9-(亚甲二氧基)-11H-吲哚[1,2-c]异喹啉盐酸盐 (27)。另外两种强效的拓扑异构酶I抑制剂，6-烯丙基-5,6-二氢-2,3-二甲氧基-8,9-(亚甲二氧基)-5,11-二氧基-11H-吲哚[1,2-c]异喹啉 (13c) 和 5,6-二氢-6-(4-羟基丁-1-基)-2,3-二甲氧基-8,9-亚甲二氧基-5,11-二氧基-(11H)-吲哚[1,2-c]异喹啉 (19a)，未对DNA进行解旋，也不影响拓扑异构酶II。

  公开号：

  US06509344B1

文献信息

• The Development of a Catalytic Synthesis of Münchnones:  A Simple Four-Component Coupling Approach to α-Amino Acid Derivatives
  作者：Rajiv Dhawan、Rania D. Dghaym、Bruce A. Arndtsen

  DOI：10.1021/ja027474d

  日期：2003.2.1

  molecules. As such, this methodology has been utilized to design a new catalytic synthesis of alpha-amino acid derivatives via a one-pot coupling of imines, carbon monoxide, and acid chloride followed by alcohol. The latter represents the first reported catalytic synthesis of alpha-amino acids directly from imine and carbon monoxide building blocks.

  已开发出一种直接从亚胺、一氧化碳和酰氯结构单元制备 1,3-恶唑鎓-5-氧化物（即 Münchnones）的新钯催化路线。这提供了 Münchnones 的直接催化合成，并且可以通过对亚胺或酰氯起始材料的简单改性来产生多种产品。Münchnones 是各种杂环和基于肽的分子的重要合成中间体。因此，该方法已被用于设计一种新的 α-氨基酸衍生物催化合成，通过亚胺、一氧化碳和酰氯的一锅偶联，然后是醇。后者代表了首次报道的直接从亚胺和一氧化碳结构单元催化合成 α-氨基酸。
• Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase I Inhibitors Lacking Substituents on the Aromatic Rings
  作者：Muthukaman Nagarajan、Andrew Morrell、Brian C. Fort、Marintha Rae Meckley、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1021/jm040025z

  日期：2004.11.1

  where it is involved in a hydrogen bonding interaction with the side chain guanidine group of Arg364. The DNA cleavage patterns observed in the presence of topoisomerase I and various indenoisoquinolines were similar, although significant differences were detected. There were also variations in the DNA cleavage pattern seen with camptothecin vs the indenoisoquinolines, which indicates that these two

  茚并异喹啉类是一类细胞毒性拓扑异构酶I抑制剂，与喜树碱相比具有某些优势，包括化合物本身的稳定性更高，以及药物-酶-DNA裂解复合物的稳定性更高。为了研究存在于先前合成的茚并异喹啉拓扑异构酶I抑制剂的芳香环上的二（甲氧基）和亚甲基二氧基取代基的可能的生物学作用，合成了一系列缺少这些取代基的化合物，并测试了其在癌细胞培养中的细胞毒性和酶的毒性。抑制活性。结果表明，芳族取代基对生物活性的贡献很小，但可观察到。关于三元复合物中未取代的茚并异喹啉与DNA和拓扑异构酶I结合的分子模型表明，内酰胺氮上的取代基突出于主沟，羰基被引出其参与的次沟。与Arg364的侧链胍基的氢键相互作用。尽管存在显着差异，但在拓扑异构酶I和各种茚并异喹啉存在下观察到的DNA切割模式相似。喜树碱与茚并异喹啉之间的DNA裂解模式也存在差异，这表明这两种拓扑异构酶I抑制剂可能以不同的方式靶向癌细胞基因组，从而产生了不同的抗癌活性谱。
• indenoisoquinolines as topoisomerase inhibitors I useful as antineoplastic agents
  申请人：Purdue Research Foundation

  公开号：EP2050452A1

  公开（公告）日：2009-04-22

  A number of indenoisoquinolines were prepared and evaluated for cytotoxicity in human cancer cell cultures and for activity vs. topoisomerase I. The two most cytotoxic indenoisoquinolines proved to be cis-6-ethyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline and cis-6-allyl-5,6,12,13-tetrahydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-(11H)indeno[1,2-c]isoquinoline. Two of the most potent topoisomerase I inhibitors were 6-(3-carboxy-1-propyl)-5,6-dihydro-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (26) and 6-ethyl-2,3-dimethoxy-8,9-(methylenedioxy)11H-indeno[1,2-c]isoquinolinium chloride (27). Two additional potent topoisomerase I inhibitors, 6-allyl-5,6-dihydro-2,3-dimethoxy-8,9-(methylenedioxy)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (13c) and 5,6-dihydro-6-(4-hydroxybut-1-yl)-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-(11H)indeno[1,2-c]isoquinoline (19a), did not unwind DNA and did not affect topoisomerase II.

  研究人员制备了多种茚并异喹啉，并对其在人类癌细胞培养物中的细胞毒性以及对拓扑异构酶 I 的活性进行了评估。结果表明，两种细胞毒性最强的茚异喹啉分别是顺式-6-乙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-（亚甲基二氧基）-5,11-二氧代-11H-茚并[1、2-c]异喹啉和顺式-6-烯丙基-5,6,12,13-四氢-2,3-二甲氧基-8,9-（亚甲基二氧基）-5,11-二氧代-11H-茚并[1,2-c]异喹啉。两种最有效的拓扑异构酶 I 抑制剂是 6-(3-羧基-1-丙基)-5,6-二氢-5,11-二氧代-11H-茚并[1,2-c]异喹啉（26）和 6-乙基-2,3-二甲氧基-8,9-(亚甲二氧基)11H-茚并[1,2-c]异喹啉氯化铵（27）。另外两种强效拓扑异构酶 I 抑制剂是 6-烯丙基-5,6-二氢-2,3-二甲氧基-8,9-（亚甲基二氧基）-5,11-二氧代-11H-茚并[1,2-c]异喹啉（13c）和 5、6-(4-羟基丁-1-基)-2,3-二甲氧基-8,9-亚甲基二氧基-5,11-二氧代-11H-茚并[1,2-c]异喹啉（19a）不会解开 DNA，也不会影响拓扑异构酶 II。
• Palladium-Catalyzed Carbonylative Cross-Coupling with Imines:  A Multicomponent Synthesis of Imidazolones
  作者：Ali R. Siamaki、Daniel A. Black、Bruce A. Arndtsen

  DOI：10.1021/jo701875b

  日期：2008.2.1

  [GRAPHICS]The palladium-catalyzed coupling of imines, chloroformates, organotin reagents, and carbon monoxide leads to the one-pot formation of ketocarbamates in good yields. These products can further be converted to highly substituted imidazolones via a cyclocondensation reaction. Overall, this methodology provides an alternative approach to imidazolones from five simple and readily available building blocks via a one-pot, multicomponent process.
• General Approach to the Coupling of Organoindium Reagents with Imines via Copper Catalysis
  作者：Daniel A. Black、Bruce A. Arndtsen

  DOI：10.1021/ol060277p

  日期：2006.5.1

  A copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides is described. This mild carbon-carbon bond forming reaction requires only one-third of an equivalent of indium reagent to proceed in high yield, with the sole byproduct being indium trichloride. The reaction demonstrates broad generality, with aryl-, heteroaryl-, vinyl-, and alkylindiums, as well as functionalized imines and acid chlorides, all providing alpha-substituted amides or N-protected amines in a single step.