2,4-diethyl-6-((trityloxy)methyl)pyridine | 1352789-09-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,4-diethyl-6-((trityloxy)methyl)pyridine
• CAS: 1352789-09-3
• 化学式: C₂₉H₂₉NO
• 分子量: 407.555
• InChiKey: OOGWUPCAAQPZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,4-diethyl-6-((trityloxy)methyl)pyridine 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4,6-Diethylpyridin-2-yl)methanol
  参考文献：
  名称：

  Heterotaxin: A TGF-β Signaling Inhibitor Identified in a Multi-Phenotype Profiling Screen in Xenopus Embryos

  摘要：

  Disruptions of anatomical left-right asymmetry result in life-threatening heterotaxic birth defects in vital organs. We performed a small molecule screen for left-right asymmetry phenotypes in Xenopus embryos and discovered a pyridine analog, heterotaxin, which disrupts both cardiovascular and digestive organ laterality and inhibits TGF-beta-dependent left-right asymmetric gene expression. Heterotaxin analogs also perturb vascular development, melanogenesis, cell migration, and adhesion, and indirectly inhibit the phosphorylation of an intracellular mediator of TGF-beta signaling. This combined phenotypic profile identifies these compounds as a class of TGF-beta signaling inhibitors. Notably, heterotaxin analogs also possess highly desirable antitumor properties, inhibiting epithelial-mesenchymal transition, angiogenesis, and tumor cell proliferation in mammalian systems. Our results suggest that assessing multiple organ, tissue, cellular, and molecular parameters in a whole organism context is a valuable strategy for identifying the mechanism of action of bioactive compounds.

  DOI：

  10.1016/j.chembiol.2010.12.008
• 作为产物：
  描述：

  1-trityloxy-2-propyne 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 草酰氯 、 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 xylenes 为溶剂， 反应 1.5h， 生成 2,4-diethyl-6-((trityloxy)methyl)pyridine
  参考文献：
  名称：

  Heterotaxin: A TGF-β Signaling Inhibitor Identified in a Multi-Phenotype Profiling Screen in Xenopus Embryos

  摘要：

  Disruptions of anatomical left-right asymmetry result in life-threatening heterotaxic birth defects in vital organs. We performed a small molecule screen for left-right asymmetry phenotypes in Xenopus embryos and discovered a pyridine analog, heterotaxin, which disrupts both cardiovascular and digestive organ laterality and inhibits TGF-beta-dependent left-right asymmetric gene expression. Heterotaxin analogs also perturb vascular development, melanogenesis, cell migration, and adhesion, and indirectly inhibit the phosphorylation of an intracellular mediator of TGF-beta signaling. This combined phenotypic profile identifies these compounds as a class of TGF-beta signaling inhibitors. Notably, heterotaxin analogs also possess highly desirable antitumor properties, inhibiting epithelial-mesenchymal transition, angiogenesis, and tumor cell proliferation in mammalian systems. Our results suggest that assessing multiple organ, tissue, cellular, and molecular parameters in a whole organism context is a valuable strategy for identifying the mechanism of action of bioactive compounds.

  DOI：

  10.1016/j.chembiol.2010.12.008