(3-chloroquinoxalin-2-yl)-(2-methoxyethyl)amine | 1436860-32-0

• 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: (3-chloroquinoxalin-2-yl)-(2-methoxyethyl)amine
• 英文别名: 3-chloro-N-(2-methoxyethyl)quinoxalin-2-amine
• CAS: 1436860-32-0
• 化学式: C₁₁H₁₂ClN₃O
• 分子量: 237.689
• InChiKey: DUQOGTBSENZEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-chloroquinoxalin-2-yl)-(2-methoxyethyl)amine 以 乙腈 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure–activity relationship study

  摘要：

  The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N-1 and N-3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.026
• 作为产物：
  描述：

  2,3-二氯喹喔啉 、 2-甲氧基乙胺 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以83.3%的产率得到(3-chloroquinoxalin-2-yl)-(2-methoxyethyl)amine
  参考文献：
  名称：

  Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure–activity relationship study

  摘要：

  The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N-1 and N-3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.026

文献信息

• Novel one-pot access to 2-formyl/acetyl-1-substituted pyrrolo[2,3-b]quinoxalines under Sonogashira reaction conditions
  作者：Ali Keivanloo、Mohammad Bakherad、Mahrokh Rahmani、Amin Rahimi

  DOI：10.1007/s00706-012-0887-1

  日期：2013.6

  A one-pot reaction of N-alkyl-3-chloroquinoxaline-2-amines with acetylenic alcohols in the presence of a Pd-Cu catalyst leads to the formation of 2-formyl/acetyl-N-substituted pyrrolo[2,3-b]quinoxalines in good to high yields. A possible mechanism for the conversion has also been proposed.