6-phenylethynyl-nicotinic acid ethyl ester | 1174028-84-2

• 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-phenylethynyl-nicotinic acid ethyl ester
• 英文别名: ethyl 6-(2-phenylethynyl)pyridine-3-carboxylate
• CAS: 1174028-84-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: NDYCXRYORJTZFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phenylethynyl-nicotinic acid ethyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以73%的产率得到6-phenylethynylnicotinic acid
  参考文献：
  名称：

  Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator

  摘要：

  This Letter describes the discovery of a novel series of mGluR5 positive allosteric modulators (PAMs). The lead compound, 11c, exhibits excellent potency (EC50 = 30 nM) in vitro, and reaches high brain levels in both rats and mice after oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.095
• 作为产物：
  描述：

  苯乙炔 、 6-碘吡啶-3-羧酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 0.17h， 以96%的产率得到6-phenylethynyl-nicotinic acid ethyl ester
  参考文献：
  名称：

  Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator

  摘要：

  This Letter describes the discovery of a novel series of mGluR5 positive allosteric modulators (PAMs). The lead compound, 11c, exhibits excellent potency (EC50 = 30 nM) in vitro, and reaches high brain levels in both rats and mice after oral administration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.095

文献信息

• Efficacy switching SAR of mGluR5 allosteric modulators: Highly potent positive and negative modulators from one chemotype
  作者：Anette Graven Sams、Gitte Kobberøe Mikkelsen、Robbin M. Brodbeck、Xiaosui Pu、Andreas Ritzén

  DOI：10.1016/j.bmcl.2011.03.103

  日期：2011.6

  A series of metabotropic glutamate 5 receptor (mGluR5) allosteric ligands with positive, negative or no modulatory efficacy is described. The ability of this series to yield both mGluR5 PAMs and NAMs with single-digit nanomolar potency is unusual, and the underlying SAR is detailed. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator
  作者：Andreas Ritzén、Rikke Sindet、Morten Hentzer、Nannette Svendsen、Robbin M. Brodbeck、Christoffer Bundgaard

  DOI：10.1016/j.bmcl.2009.04.095

  日期：2009.6

  This Letter describes the discovery of a novel series of mGluR5 positive allosteric modulators (PAMs). The lead compound, 11c, exhibits excellent potency (EC50 = 30 nM) in vitro, and reaches high brain levels in both rats and mice after oral administration. (C) 2009 Elsevier Ltd. All rights reserved.