2-(3-(4-methoxybenzyloxy)propyl)-4,6-dimethylpyridine-3,5-dicarbaldehyde | 941693-23-8

• 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: 2-(3-(4-methoxybenzyloxy)propyl)-4,6-dimethylpyridine-3,5-dicarbaldehyde
• 英文别名: 2-[3-[(4-Methoxyphenyl)methoxy]propyl]-4,6-dimethylpyridine-3,5-dicarbaldehyde
• CAS: 941693-23-8
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: MYVKRUIICUDXBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-(4-methoxybenzyloxy)propyl)-4,6-dimethylpyridine-3,5-dicarbaldehyde 、 (1-壬基)三苯基溴化磷 生成 6,8-bis(dec-1-enyl)-5,7-dimethyl-2,3-dihydro-1H-indolizin-4-ium;chloride
  参考文献：
  名称：

  Total Synthesis of Anibamine, a Novel Natural Product as a Chemokine Receptor CCR5 Antagonist

  摘要：

  The total synthesis of anibamine, the first and only natural product known as a chemokine receptor CCR5 antagonist, is reported herein. Anibamine was synthesized from acetylacetone and cyanoacetamide in 10 steps.

  DOI：

  10.1021/ol070748n
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal copper(l) iodide 、 D(+)-10-樟脑磺酸 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， -70.0~20.0 ℃ 、393.01 kPa 条件下， 反应 10.67h， 生成 2-(3-(4-methoxybenzyloxy)propyl)-4,6-dimethylpyridine-3,5-dicarbaldehyde
  参考文献：
  名称：

  Total Synthesis of Anibamine, a Novel Natural Product as a Chemokine Receptor CCR5 Antagonist

  摘要：

  The total synthesis of anibamine, the first and only natural product known as a chemokine receptor CCR5 antagonist, is reported herein. Anibamine was synthesized from acetylacetone and cyanoacetamide in 10 steps.

  DOI：

  10.1021/ol070748n

文献信息

• The natural product CCR5 antagonist anibamine and its analogs as anti-prostate cancer agents
  作者：Kendra M. Haney、Feng Zhang、Christopher K. Arnatt、Yunyun Yuan、Guo Li、Joy L. Ware、David A. Gewirtz、Yan Zhang

  DOI：10.1016/j.bmcl.2011.07.058

  日期：2011.9

  Prostate cancer is a leading cause of death among males in the United States. As the chemokine receptor CCR5 is over-expressed in more aggressive forms of prostate cancer, and is also a critical receptor in inflammation, chemokine receptor CCR5 antagonists could potentially act as anti-prostate cancer agents. Anibamine, a natural product CCR5 antagonist, provides a unique molecular scaffold for the generation of novel analogs with possible anti-prostate cancer activity. A series of analogs of anibamine were designed, synthesized and tested against several prostate cancer cell lines. The analogs all acted as CCR5 antagonists at micromolar range affinity to the receptor while their anti-proliferative activity varied depending on the cell line type and their chemical structural properties. Further basal cytotoxicity characterization on these compounds indicated some of them may be suitable for in vivo studies. Published by Elsevier Ltd.