(6-Ethylpyridine-2,4-diyl)dimethanol | 111599-44-1

• 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: (6-Ethylpyridine-2,4-diyl)dimethanol
• 英文别名: [2-ethyl-6-(hydroxymethyl)pyridin-4-yl]methanol
• CAS: 111599-44-1
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: BSKVNTAPKJTFHA-UHFFFAOYSA-N

物化性质

• 沸点：
  322.3±37.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 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 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (6-Ethylpyridine-2,4-diyl)dimethanol
  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。
• Inhibitors of phosphoglycerate dehydrogenase (PHGDH) and uses thereof
  申请人：Whitehead Institute for Biomedical Research

  公开号：US11225469B2

  公开（公告）日：2022-01-18

  The present invention provides compounds of Formula (II), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, pro-drugs, and compositions thereof. Also provided are methods and kits involving the compounds of Formula (I), (II) or (III) for treating diseases associated with the over-expression of phosphoglycerate dehydrogenase (PHGDH) in a subject, such as proliferative diseases (e.g., cancers (e.g., breast cancer, ER negative breast cancer, melanoma, cervical cancer), benign neoplasms, diseases associated with angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases). Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the activity of PHGDH or inhibit the serine biosynthetic pathway, or both.

  本发明提供了式(II)化合物及其药学上可接受的盐、溶液剂、水合物、多晶型、共晶体、同分异构体、立体异构体、同位素标记的衍生物、原药及其组合物。还提供了涉及式(I)、(II)或(III)化合物的方法和试剂盒，用于治疗与受试者体内磷酸甘油脱氢酶（PHGDH）过度表达有关的疾病，如增殖性疾病（如癌症（如乳腺癌、ER阴性乳腺癌、黑色素瘤、宫颈癌）、良性肿瘤、与血管生成有关的疾病、炎症性疾病、自身炎症性疾病和自身免疫性疾病）。使用本发明的化合物或组合物治疗增殖性疾病患者，可抑制 PHGDH 的活性或抑制丝氨酸生物合成途径，或两者兼而有之。
• INHIBITORS OF PHOSPHOGLYCERATE DEHYDROGENASE (PHGDH) AND USES THEREOF
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20180105508A1

  公开（公告）日：2018-04-19

  The present invention provides compounds pounds of Formula (II), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, pro-drugs, and compositions thereof. Also provided are methods and kits involving the compounds of Formula (I), (II) or (III) for treating diseases associated with the over-expression of phosphoglycerate dehydrogenase (PHGDH) in a subject, such as proliferative diseases (e.g., cancers (e.g., breast cancer, ER negative breast cancer, melanoma, cervical cancer), benign neoplasms, diseases associated with angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases). Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the activity of PHGDH or inhibit the serine biosynthetic pathway, or both.
• 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.