17,18-dimethoxyluotonin A | 704912-41-4

• 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: 17,18-dimethoxyluotonin A
• 英文别名: 6,7-dimethoxy-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,13,15,17,19-nonaen-10-one
• CAS: 704912-41-4
• 化学式: C₂₀H₁₅N₃O₃
• 分子量: 345.357
• InChiKey: PSDWYAFCXLKALA-UHFFFAOYSA-N

物化性质

• 熔点：
  282 °C (decomp)
• 沸点：
  596.5±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17,18-dimethoxyluotonin A 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以10%的产率得到17,18-dihydroxyluotonin A
  参考文献：
  名称：

  Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives

  摘要：

  A series of A-ring and E-ring analogues of the natural product luotonin A, a known topoisomerase I poison, was evaluated for growth inhibition in human carcinoma and leukemia cell lines. Rational design of structures was based on analogues of the related alkaloid camptothecin, which has been demonstrated to exert cytotoxic effects by the same mechanism of action. When compared to luotonin A, several compounds exhibited an improved topoisomerase I-dependent growth inhibition of a human leukemia cell line. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.067
• 作为产物：
  描述：

  在 palladium diacetate potassium acetate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 17,18-dimethoxyluotonin A
  参考文献：
  名称：

  Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives

  摘要：

  A series of A-ring and E-ring analogues of the natural product luotonin A, a known topoisomerase I poison, was evaluated for growth inhibition in human carcinoma and leukemia cell lines. Rational design of structures was based on analogues of the related alkaloid camptothecin, which has been demonstrated to exert cytotoxic effects by the same mechanism of action. When compared to luotonin A, several compounds exhibited an improved topoisomerase I-dependent growth inhibition of a human leukemia cell line. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.067

文献信息

• Synthesis and topoisomerase I inhibitory properties of luotonin A analogues
  作者：Ali Cagir、Brian M. Eisenhauer、Rong Gao、Shannon J. Thomas、Sidney M. Hecht

  DOI：10.1016/j.bmc.2004.08.052

  日期：2004.12

  reaction proceeded to a single product. In contrast when the reaction was carried out in tetrahydrofuran or in phosphorus oxychloride, an additional isomeric product was obtained. The luotonin A analogues were evaluated for their ability to effect stabilization of the covalent binary complex formed between human topoisomerase I and DNA, and for cytotoxicity toward a yeast strain expressing the human

  萤光素A是一种天然存在的吡咯并喹唑啉喹啉生物碱，先前已证明是拓扑异构酶I毒物。现在，在氧氯化磷存在下，通过邻氨基苯甲酸衍生物与1,2-二氢吡咯并[3,4-b]喹啉-3-one的缩合反应，制得了许多褪黑素A衍生物。当使用二氯甲烷作为溶剂时，反应进行为单一产物。相反，当反应在四氢呋喃或三氯氧磷中进行时，获得了另外的异构体产物。评价了褪黑素A类似物对人拓扑异构酶I和DNA之间形成的共价二元复合物的稳定作用的能力，以及对表达人拓扑异构酶I的酵母菌株的细胞毒性。
• 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.