(3E,5E)-1-methyl-3,5-bis(quinolin-6-ylmethylene)-piperidin-4-one | 1261138-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3E,5E)-1-methyl-3,5-bis(quinolin-6-ylmethylene)-piperidin-4-one
• 英文别名: (3E,5E)-1-methyl-3,5-bis(quinolin-6-ylmethylidene)piperidin-4-one
• CAS: 1261138-64-0
• 化学式: C₂₆H₂₁N₃O
• 分子量: 391.472
• InChiKey: LZVCKZZSEVVNOH-HOFJZWJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-1-methyl-3,5-bis(quinolin-6-ylmethylene)-piperidin-4-one 、 碘甲烷 以 环丁砜 为溶剂， 反应 4.0h， 以72%的产率得到6,6'-(1E,1'E)-(1,1-dimethyl-4-oxopiperidinium-3,5-diylidene)bis(methan-1-yl-1-ylidene)bis(1-methylquinolinium) iodide
  参考文献：
  名称：

  Bisaryldiketene derivatives: A new class of selective ligands for c-myc G-quadruplex DNA

  摘要：

  A series of bisaryldiketene derivatives were designed and synthesized as a new class of specific G-quadruplex ligands. The ligand-quadruplex interactions were further evaluated by FRET, ITC, and PCR stop assay. In contrast to most of the G-quadruplex ligands reported so far, which comprise an extended aromatic ring, these compounds are neither polycyclic nor macrocyclic, but have a non-aromatic and relative flexible linker between two quinoline moieties enabling the conformation of compounds to be flexible. Our results showed that these bisaryldiketene derivatives could selectively recognize G-quadruplex DNA rather than binding to duplex DNA. Moreover, they showed promising discrimination between different G-quadruplex DNA. The primary binding affinity of ligand M2 for c-myc G-quadruplex DNA was over 200 times larger than that for telomere G-quadruplex DNA. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.021
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 喹啉-6-甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以74%的产率得到(3E,5E)-1-methyl-3,5-bis(quinolin-6-ylmethylene)-piperidin-4-one
  参考文献：
  名称：

  Bisaryldiketene derivatives: A new class of selective ligands for c-myc G-quadruplex DNA

  摘要：

  A series of bisaryldiketene derivatives were designed and synthesized as a new class of specific G-quadruplex ligands. The ligand-quadruplex interactions were further evaluated by FRET, ITC, and PCR stop assay. In contrast to most of the G-quadruplex ligands reported so far, which comprise an extended aromatic ring, these compounds are neither polycyclic nor macrocyclic, but have a non-aromatic and relative flexible linker between two quinoline moieties enabling the conformation of compounds to be flexible. Our results showed that these bisaryldiketene derivatives could selectively recognize G-quadruplex DNA rather than binding to duplex DNA. Moreover, they showed promising discrimination between different G-quadruplex DNA. The primary binding affinity of ligand M2 for c-myc G-quadruplex DNA was over 200 times larger than that for telomere G-quadruplex DNA. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.021

文献信息

• Bisaryldiketene derivatives: A new class of selective ligands for c-myc G-quadruplex DNA
  作者：Dan Peng、Jia-Heng Tan、Shuo-Bin Chen、Tian-Miao Ou、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.bmc.2010.10.021

  日期：2010.12

  A series of bisaryldiketene derivatives were designed and synthesized as a new class of specific G-quadruplex ligands. The ligand-quadruplex interactions were further evaluated by FRET, ITC, and PCR stop assay. In contrast to most of the G-quadruplex ligands reported so far, which comprise an extended aromatic ring, these compounds are neither polycyclic nor macrocyclic, but have a non-aromatic and relative flexible linker between two quinoline moieties enabling the conformation of compounds to be flexible. Our results showed that these bisaryldiketene derivatives could selectively recognize G-quadruplex DNA rather than binding to duplex DNA. Moreover, they showed promising discrimination between different G-quadruplex DNA. The primary binding affinity of ligand M2 for c-myc G-quadruplex DNA was over 200 times larger than that for telomere G-quadruplex DNA. (C) 2010 Elsevier Ltd. All rights reserved.