2-[(1-formyl-5,6-dihydro-4H-indolo[1,2,3-ef]pyrrolo[3,2,1-jk][1,5]benzodiazepin-5-yl)oxy]ethyl 4-methylbenzenesulfonate

• 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: 2-[(1-formyl-5,6-dihydro-4H-indolo[1,2,3-ef]pyrrolo[3,2,1-jk][1,5]benzodiazepin-5-yl)oxy]ethyl 4-methylbenzenesulfonate
• 英文别名: 2-[(12-Formyl-1,14-diazapentacyclo[9.6.2.02,7.08,18.014,19]nonadeca-2,4,6,8(18),9,11(19),12-heptaen-16-yl)oxy]ethyl 4-methylbenzenesulfonate；2-[(12-formyl-1,14-diazapentacyclo[9.6.2.02,7.08,18.014,19]nonadeca-2,4,6,8(18),9,11(19),12-heptaen-16-yl)oxy]ethyl 4-methylbenzenesulfonate
• 化学式: C₂₇H₂₄N₂O₅S
• 分子量: 488.564
• InChiKey: RMULYBJVYGCBBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1-formyl-5,6-dihydro-4H-indolo[1,2,3-ef]pyrrolo[3,2,1-jk][1,5]benzodiazepin-5-yl)oxy]ethyl 4-methylbenzenesulfonate 、 二乙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以84%的产率得到5-[2-(diethylamino)ethoxy]-5,6-dihydro-4H-indolo[1,2,3-ef]pyrrolo[3,2,1-jk][1,5]benzodiazepine-1-carbaldehyde
  参考文献：
  名称：

  Synthesis and activities of new indolopyrrolobenzodiazepine derivatives toward acute myeloid leukemia cells

  摘要：

  The synthesis of new indolopyrrolobenzodiazepine derivatives is described. Six compounds were selected for evaluation of cytotoxicity towards acute myeloid leukemia (AML) cells and normal fibroblasts. One compound (29) showed selective AML cell death induction. Its action was only partly overcome by knock-down of p53 or Bcl-2 overexpression, suggesting a strong activation of intrinsic apoptotic pathways. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.031
• 作为产物：
  描述：

  1,10-dihydropyrrolo[2,3-a]carbazole 在 lithium aluminium tetrahydride 、 sodium hydride 、 caesium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 10.0h， 生成 2-[(1-formyl-5,6-dihydro-4H-indolo[1,2,3-ef]pyrrolo[3,2,1-jk][1,5]benzodiazepin-5-yl)oxy]ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and activities of new indolopyrrolobenzodiazepine derivatives toward acute myeloid leukemia cells

  摘要：

  The synthesis of new indolopyrrolobenzodiazepine derivatives is described. Six compounds were selected for evaluation of cytotoxicity towards acute myeloid leukemia (AML) cells and normal fibroblasts. One compound (29) showed selective AML cell death induction. Its action was only partly overcome by knock-down of p53 or Bcl-2 overexpression, suggesting a strong activation of intrinsic apoptotic pathways. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.031

文献信息

• Synthesis and activities of new indolopyrrolobenzodiazepine derivatives toward acute myeloid leukemia cells
  作者：Francis Giraud、Marion Bourhis、Edris Ebrahimi、Lars Herfindal、Romy Roy Choudhury、Ronja Bjørnstad、Stein Ove Døskeland、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.bmc.2015.10.031

  日期：2015.11

  The synthesis of new indolopyrrolobenzodiazepine derivatives is described. Six compounds were selected for evaluation of cytotoxicity towards acute myeloid leukemia (AML) cells and normal fibroblasts. One compound (29) showed selective AML cell death induction. Its action was only partly overcome by knock-down of p53 or Bcl-2 overexpression, suggesting a strong activation of intrinsic apoptotic pathways. (C) 2015 Elsevier Ltd. All rights reserved.