9-benzyl-7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one | 1333109-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-benzyl-7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one
• 英文别名: 9-benzyl-7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1-one
• CAS: 1333109-66-2
• 化学式: C₃₃H₂₈N₂O₇
• 分子量: 564.595
• InChiKey: UBPJACWLZBZINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-benzyl-7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one 在 aluminum (III) chloride 、 苯甲醚 、 甲醇 作用下， 反应 5.0h， 以20%的产率得到7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one
  参考文献：
  名称：

  Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D

  摘要：

  A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a beta-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.056
• 作为产物：
  描述：

  tert-butyl (1,2-bis(4-isopropoxy-3-methoxyphenyl)-2-oxoethyl)carbamate 在 aluminum (III) chloride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.25h， 生成 9-benzyl-7-hydroxy-3,4-bis(4-hydroxy-3-methoxyphenyl)-6-methoxy-2H-pyrido[3,4-b]indol-1(9H)-one
  参考文献：
  名称：

  Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D

  摘要：

  A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a beta-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.056

文献信息

• Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D
  作者：Salvatore Cananzi、Lucio Merlini、Roberto Artali、Giovanni Luca Beretta、Nadia Zaffaroni、Sabrina Dallavalle

  DOI：10.1016/j.bmc.2011.06.056

  日期：2011.8

  A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a beta-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line. (C) 2011 Elsevier Ltd. All rights reserved.