tert-butyl (5-(phenylethynyl)pyridin-2-yl)carbamate | 1259524-97-4

• 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: tert-butyl (5-(phenylethynyl)pyridin-2-yl)carbamate
• 英文别名: tert-butyl N-[5-(2-phenylethynyl)pyridin-2-yl]carbamate
• CAS: 1259524-97-4
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: BUMIGKIMMYYJMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (5-(phenylethynyl)pyridin-2-yl)carbamate 在 potassium permanganate 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 水 、 丙酮 为溶剂， 以64%的产率得到tert-butyl (5-(2-oxo-2-phenylacetyl)pyridin-2-yl)carbamate
  参考文献：
  名称：

  Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors

  摘要：

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.

  DOI：

  10.1021/jm101101q
• 作为产物：
  描述：

  苯乙炔 、 2-(Boc-氨基)-5-溴吡啶 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 以74%的产率得到tert-butyl (5-(phenylethynyl)pyridin-2-yl)carbamate
  参考文献：
  名称：

  Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors

  摘要：

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.

  DOI：

  10.1021/jm101101q

文献信息

• Structure−Activity Relationships of Substituted 1-Pyridyl-2-phenyl-1,2-ethanediones: Potent, Selective Carboxylesterase Inhibitors
  作者：Brandon M. Young、Janice L. Hyatt、David C. Bouck、Taosheng Chen、Parimala Hanumesh、Jeanine Price、Vincent A. Boyd、Philip M. Potter、Thomas R. Webb

  DOI：10.1021/jm101101q

  日期：2010.12.23

  Inhibition of intestinal carboxylesterases may allow modification of the pharmacokinetics/pharmacodynamic profile of existing drugs by altering half-life or toxicity. Since previously identified diarylethane-1,2-dione inhibitors are decidedly hydrophobic, a modified dione scaffold was designed and elaborated into a > 300 member library, which was subsequently screened to establish the SAR for esterase inhibition. This allowed the identification of single digit nanomolar hiCE inhibitors that showed improvement in selectivity and measured solubility.