7,8,9,10-tetrahydroluotonin A

• 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: 7,8,9,10-tetrahydroluotonin A
• 英文别名: 3,11,21-Triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),13,15,17,19-heptaen-10-one
• 化学式: C₁₈H₁₅N₃O
• 分子量: 289.337
• InChiKey: ALTRIBDAHXVMAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  色氨酸A 在 镍 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到7,8,9,10-tetrahydroluotonin A
  参考文献：
  名称：

  Total synthesis of luotonin A and 14-substituted analogues

  摘要：

  一种新的简明合成方法成功地从之前描述的化合物乙基4-氧-3,4-二氢喹唑啉-2-羧酸酯和1-(2-硝基苯基)丙-2-烯-1-酮中合成了luotonin A。使用14-氯luotonin A作为关键中间体，制备了新的14取代的luotonin A类似物。

  DOI：

  10.1039/b707684c

文献信息

• Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives
  作者：Yi Ju、Feng Liu、Chaozhong Li

  DOI：10.1021/ol901305q

  日期：2009.8.20

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.
• Synthesis and biochemical properties of E-ring modified luotonin A derivatives
  作者：Ali Cagir、Shannon H Jones、Brian M Eisenhauer、Rong Gao、Sidney M Hecht

  DOI：10.1016/j.bmcl.2004.02.069

  日期：2004.5

  Luotonin A is a cytotoxic pyrroloquinazolinoquinoline alkaloid that has been shown to stabilize the human topoisomerase I-DNA covalent binary complex in the same fashion Lis the antitumor alkaloid camptothecin. A study of the structural elements in luotonin A required for binary complex stabilization has revealed key differences relative to those required for camptothecin. (C) 2004 Elsevier Ltd. All rights reserved.
• Intramolecular Formal [4 + 2] Cycloaddition of Nitriles with Amides Triggered by TMSOTf/Et₃N: Highly Efficient Construction of Pyrrolo[1,2-<i>a</i>]pyrimidin-4(6<i>H</i>)-ones
  作者：Feng Liu、Chaozhong Li

  DOI：10.1021/jo900907h

  日期：2009.8.7

  By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.