N'-(4-aminophenyl)-N-[2-(diethylamino)ethyl]hexanediamide | 754227-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(4-aminophenyl)-N-[2-(diethylamino)ethyl]hexanediamide
• CAS: 754227-34-4
• 化学式: C₁₈H₃₀N₄O₂
• 分子量: 334.462
• InChiKey: PMRWMZYOPLDFIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[9-chloro-6-(3-pyrrolidin-1-yl-propionylamino)-acridin-3-yl]-3-pyrrolidin-1-yl-propionoamide 、 N'-(4-aminophenyl)-N-[2-(diethylamino)ethyl]hexanediamide 以 甲醇 为溶剂， 生成 N1-(4-(3,6-bis(3-(pyrrolidin-1-yl)propanamido)acridin-9-ylamino)phenyl)-N6-(2-(diethylamino)ethyl)adipamide
  参考文献：
  名称：

  Synthesis, biophysical and biological evaluation of 3,6-bis-amidoacridines with extended 9-anilino substituents as potent G-quadruplex-binding telomerase inhibitors

  摘要：

  Telomerase and telomere maintenance are emerging targets for the treatment of human cancers. We report here on the targeting of the telomere-telomerase complex with a series of small molecules based on an acridine platform. A series of 3,6-bis-amidoacridines with extended 9-anilino sidechains were designed and synthesised as potential telomeric G-quadruplex DNA (G4) interacting compounds. G4-stabilisation was assessed using a high-throughput FRET (fluorescence resonance energy transfer) assay and telomerase inhibition quantified by a modified TRAP (telomerase repeat amplification protocol) method. Within the series, the compounds showed significant G4-stabilising ability (DeltaT(m) values of 25-36degreesC at 1 muM concentration) and telomerase inhibition in the nanomolar region ((EC50)-E-tel values of 80-318 nM). Furthermore, a direct correlation between the FRET and TRAP assays was observed, supporting the use of the rapid screening FRET assay for early assessment of potential G4-stabilising telomerase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.090
• 作为产物：
  描述：

  己二酸酐 在 palladium on activated charcoal ammonium formate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 N'-(4-aminophenyl)-N-[2-(diethylamino)ethyl]hexanediamide
  参考文献：
  名称：

  Synthesis, biophysical and biological evaluation of 3,6-bis-amidoacridines with extended 9-anilino substituents as potent G-quadruplex-binding telomerase inhibitors

  摘要：

  Telomerase and telomere maintenance are emerging targets for the treatment of human cancers. We report here on the targeting of the telomere-telomerase complex with a series of small molecules based on an acridine platform. A series of 3,6-bis-amidoacridines with extended 9-anilino sidechains were designed and synthesised as potential telomeric G-quadruplex DNA (G4) interacting compounds. G4-stabilisation was assessed using a high-throughput FRET (fluorescence resonance energy transfer) assay and telomerase inhibition quantified by a modified TRAP (telomerase repeat amplification protocol) method. Within the series, the compounds showed significant G4-stabilising ability (DeltaT(m) values of 25-36degreesC at 1 muM concentration) and telomerase inhibition in the nanomolar region ((EC50)-E-tel values of 80-318 nM). Furthermore, a direct correlation between the FRET and TRAP assays was observed, supporting the use of the rapid screening FRET assay for early assessment of potential G4-stabilising telomerase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.090