(2S,4S)-N-[2-nitrobenzoyl]-4-azidopyrrolidine-2-carboxaldehyde diethylthioacetal | 1018783-17-9

• 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: (2S,4S)-N-[2-nitrobenzoyl]-4-azidopyrrolidine-2-carboxaldehyde diethylthioacetal
• CAS: 1018783-17-9
• 化学式: C₁₆H₂₁N₅O₃S₂
• 分子量: 395.506
• InChiKey: CXJBYPPWAKKHAZ-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  112.21
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-N-[2-nitrobenzoyl]-4-azidopyrrolidine-2-carboxaldehyde diethylthioacetal 、 (2S)-N-[5-methoxy-4-(2-propynyloxy)-2-nitrobenzoyl]-pyrrolidine-2-carboxaldehyde diethyl-dithioacetal 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of C8–C8/C2–C8-linked triazolo pyrrolobenzodiazepine dimers by employing ‘click’ chemistry and their DNA-binding affinity

  摘要：

  A series of 1,2,3-triazole-containing pyrrolo[2,1-c][1,4]benzodiazepine dimers have been prepared efficiently by employing a 'click' chemistry protocol. This method involves 1,3-dipolar cycloaddition of terminal alkynes with organic azides using a Cu(I)-catalyst. Further, these molecules exhibited interesting DNA-binding affinity profiles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.006
• 作为产物：
  描述：

  、 乙硫醇 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(2S,4S)-N-[2-nitrobenzoyl]-4-azidopyrrolidine-2-carboxaldehyde diethylthioacetal
  参考文献：
  名称：

  Synthesis of C8–C8/C2–C8-linked triazolo pyrrolobenzodiazepine dimers by employing ‘click’ chemistry and their DNA-binding affinity

  摘要：

  A series of 1,2,3-triazole-containing pyrrolo[2,1-c][1,4]benzodiazepine dimers have been prepared efficiently by employing a 'click' chemistry protocol. This method involves 1,3-dipolar cycloaddition of terminal alkynes with organic azides using a Cu(I)-catalyst. Further, these molecules exhibited interesting DNA-binding affinity profiles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.006

文献信息

• Synthesis of 1,2,3-triazole-linked pyrrolobenzodiazepine conjugates employing ‘click’ chemistry: DNA-binding affinity and anticancer activity
  作者：Ahmed Kamal、N. Shankaraiah、V. Devaiah、K. Laxma Reddy、Aarti Juvekar、Subrata Sen、Nisha Kurian、Surekha Zingde

  DOI：10.1016/j.bmcl.2007.12.063

  日期：2008.2

  1,2,3-Triazole based molecules are useful pharmacophores for several DNA-alkylating and cross-linking agents. A series of A/C8, C/C2 and A/C8-C/C2-linked 1,2,3-triazole-PBD conjugates have been synthesized by employing 'click' chemistry. These molecules have exhibited promising DNA-binding affinity and anticancer activity in selected human cancer cell lines. (c) 2007 Elsevier Ltd. All rights reserved.