heterotaxin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: heterotaxin
• 英文别名: 4-Butyl-6-ethylpyridine-2-methanol；(4-butyl-6-ethylpyridin-2-yl)methanol
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: MCIQCEZFJPDFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  heterotaxin 在 manganese(IV) oxide 、 sodium chlorite 、 2-甲基-2-丁烯 、 磷酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 4-butyl-6-ethylpyridine-2-carboxylic acid
  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：

  5-ethyl-1,1-diisopropyl-7-((trityloxy)methyl)-1,3-dihydro-[1,2]oxasilolo[3,4-c]pyridine 在 盐酸 、 正丁基锂 、 草酰氯 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 heterotaxin
  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

文献信息

• Pyridines via solid-supported [2 + 2 + 2] cyclotrimerization
  作者：Ramesh S. Senaiar、Douglas D. Young、Alexander Deiters

  DOI：10.1039/b515901f

  日期：——

  The formation of pyridines via a crossed [2 + 2 + 2] cycloaddition has been achieved on a solid-support for the first time.

  通过交叉的[2 + 2 + 2]环加成反应首次在固体载体上形成吡啶。
• Heterotaxin: A TGF-β Signaling Inhibitor Identified in a Multi-Phenotype Profiling Screen in Xenopus Embryos
  作者：Michael K. Dush、Andrew L. McIver、Meredith A. Parr、Douglas D. Young、Julie Fisher、Donna R. Newman、Philip L. Sannes、Marlene L. Hauck、Alexander Deiters、Nanette Nascone-Yoder

  DOI：10.1016/j.chembiol.2010.12.008

  日期：2011.2

  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.