7-methoxyquinolino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one | 704912-40-3

• 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-methoxyquinolino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one
• 英文别名: 7-methoxyluotonine A；16-methoxyluotonin A；5-methoxy-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,13,15,17,19-nonaen-10-one
• CAS: 704912-40-3
• 化学式: C₁₉H₁₃N₃O₂
• 分子量: 315.331
• InChiKey: WKZGVVMYERFXBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxyquinolino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one 在 氢溴酸 作用下， 以10%的产率得到5-Hydroxy-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,13,15,17,19-nonaen-10-one
  参考文献：
  名称：

  褪黑素A类似物的合成和拓扑异构酶I抑制特性。

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2004.08.052
• 作为产物：
  描述：

  1-(2-溴喹啉-3-基 )甲胺 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 氰化四乙基铵 、 copper(l) cyanide 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 7-methoxyquinolino[2',3':3,4]pyrrolo[2,1-b]quinazolin-11(13H)-one
  参考文献：
  名称：

  Concise Approach to Mono- and Disubstituted Luotonin A Analogs and Their Cytotoxicity Test

  摘要：

  A concise approach for the preparation of luotonin A analogs has been developed. The new synthetic route contains an anion-assisted intramolecular double hetero Diels-Alder reaction and a direct oxidative cross coupling reaction. Some synthetic luotonin A analogs show cytotoxic activities against Daudi and Jurkat human cancer cells as potent as camptothecin.

  DOI：

  10.3987/com-17-s(t)6

文献信息

• Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives
  作者：Kassoum Nacro、Conxiang (Charles) Zha、Peter R. Guzzo、R. Jason Herr、Denise Peace、Thomas D. Friedrich

  DOI：10.1016/j.bmc.2007.03.067

  日期：2007.6

  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.
• Synthesis and cytotoxic activity of substituted Luotonin A derivatives
  作者：Sabrina Dallavalle、Lucio Merlini、Giovanni Luca Beretta、Stella Tinelli、Franco Zunino

  DOI：10.1016/j.bmcl.2004.09.039

  日期：2004.12

  Luotonin A is a cytotoxic alkaloid that has been shown to inhibit topoisomerase I via stabilization of the binary complex topoisomerase-DNA in the same fashion as camptothecin. The synthesis and the cytotoxic activity on the lung carcinoma cell line H460 of a series of derivatives of Luotonin A is reported. The compounds inhibit topoisomerase I but show weak cytotoxic activity, thus confirming the peculiarity of ring E of camptothecin for antitumor activity. (C) 2004 Published by Elsevier Ltd.
• 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.
• Concise Approach to Mono- and Disubstituted Luotonin A Analogs and Their Cytotoxicity Test
  作者：Masahiro Toyota、Natsuko Kagawa、Kimiko Nishimura、Shinya Abe

  DOI：10.3987/com-17-s(t)6

  日期：——

  A concise approach for the preparation of luotonin A analogs has been developed. The new synthetic route contains an anion-assisted intramolecular double hetero Diels-Alder reaction and a direct oxidative cross coupling reaction. Some synthetic luotonin A analogs show cytotoxic activities against Daudi and Jurkat human cancer cells as potent as camptothecin.
• 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。