Methyl 2-(2-ethylphenyl)-4-(pyridin-3-yloxymethyl)benzoate | 1026224-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-(2-ethylphenyl)-4-(pyridin-3-yloxymethyl)benzoate
• CAS: 1026224-92-9
• 化学式: C₂₂H₂₁NO₃
• 分子量: 347.414
• InChiKey: JVWNNVPMUOREOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-(2-ethylphenyl)-4-(pyridin-3-yloxymethyl)benzoate 在 lithium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 methyl (2S)-2-[[2-(2-ethylphenyl)-4-(pyridin-3-yloxymethyl)benzoyl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Potent and Selective Non-Cysteine-Containing Inhibitors of Protein Farnesyltransferase

  摘要：

  Potent and selective non-thiol-containing inhibitors of protein farnesyltransferase are described. FTI-276 (1) was transformed into pyridyl ether analogue 19. The potency of pyridyl ether 19 was improved by modification of the biphenyl core to that of an o-tolyl substituted biphenyl core to give 29. In addition to 0.4 nM in vitro potency, 29 displayed 350 nM potency in whole cells as the parent carboxylic acid. The o-tolyl biphenyl core dramatically and unexpectedly enhanced the potency of other compounds as exemplified by 46, 47, 48, and 49.

  DOI：

  10.1021/jm980298s
• 作为产物：
  描述：

  2-氨基对苯二甲酸二甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 氯化亚砜 、 18-冠醚-6 、 硫酸 、 二异丁基氢化铝 、 caesium carbonate 、 尿素 、 potassium iodide 、 lithium chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.08h， 生成 Methyl 2-(2-ethylphenyl)-4-(pyridin-3-yloxymethyl)benzoate
  参考文献：
  名称：

  Potent and Selective Non-Cysteine-Containing Inhibitors of Protein Farnesyltransferase

  摘要：

  Potent and selective non-thiol-containing inhibitors of protein farnesyltransferase are described. FTI-276 (1) was transformed into pyridyl ether analogue 19. The potency of pyridyl ether 19 was improved by modification of the biphenyl core to that of an o-tolyl substituted biphenyl core to give 29. In addition to 0.4 nM in vitro potency, 29 displayed 350 nM potency in whole cells as the parent carboxylic acid. The o-tolyl biphenyl core dramatically and unexpectedly enhanced the potency of other compounds as exemplified by 46, 47, 48, and 49.

  DOI：

  10.1021/jm980298s

文献信息

• Potent and Selective Non-Cysteine-Containing Inhibitors of Protein Farnesyltransferase
  作者：David J. Augeri、Stephen J. O'Connor、Dave Janowick、Bruce Szczepankiewicz、Gerry Sullivan、John Larsen、Douglas Kalvin、Jerry Cohen、Edward Devine、Haichao Zhang、Sajeev Cherian、Badr Saeed、Shi-Chung Ng、Saul Rosenberg

  DOI：10.1021/jm980298s

  日期：1998.10.1

  Potent and selective non-thiol-containing inhibitors of protein farnesyltransferase are described. FTI-276 (1) was transformed into pyridyl ether analogue 19. The potency of pyridyl ether 19 was improved by modification of the biphenyl core to that of an o-tolyl substituted biphenyl core to give 29. In addition to 0.4 nM in vitro potency, 29 displayed 350 nM potency in whole cells as the parent carboxylic acid. The o-tolyl biphenyl core dramatically and unexpectedly enhanced the potency of other compounds as exemplified by 46, 47, 48, and 49.