5-(2-hydroxyethyl)-1-methylpyridin-2(1H)-one | 32897-20-4

• 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: 5-(2-hydroxyethyl)-1-methylpyridin-2(1H)-one
• 英文别名: 1-Methyl-3-(2-hydroxyethyl)-pyridon-(6)；5-(2-hydroxy-ethyl)-1-methyl-1H-pyridin-2-one；5-(2-Hydroxyethyl)-1-methylpyridin-2-one
• CAS: 32897-20-4
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: XXOIHQQNLNIITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyethyl)-1-methylpyridin-2(1H)-one 在 lithium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-(2-(2-(2-(3,5-dimethylphenyl)-5-(2-(2-fluoro-6-(trifluoromethyl)phenyl)acetyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)propylamino)ethyl)-1-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Identification of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives as novel GnRH receptor antagonists

  摘要：

  A novel series of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives were designed and synthesized as GnRH receptor antagonists. SAR studies led to a series of highly active molecules against both the rat and human receptors. Furthermore, one potent compound, 17j, demonstrated dose-dependent LH suppression in castrated rats. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.009
• 作为产物：
  描述：

  5-溴-1-甲基-2(1H)-吡啶酮 在 bis-triphenylphosphine-palladium(II) chloride 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2-hydroxyethyl)-1-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Identification of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives as novel GnRH receptor antagonists

  摘要：

  A novel series of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives were designed and synthesized as GnRH receptor antagonists. SAR studies led to a series of highly active molecules against both the rat and human receptors. Furthermore, one potent compound, 17j, demonstrated dose-dependent LH suppression in castrated rats. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.009

文献信息

• Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity
  作者：Wallace T. Ashton、Rosemary M. Sisco、Gerard R. Kieczykowski、Yi Tien Yang、Joel B. Yudkovitz、Jisong Cui、George R. Mount、Rena Ning Ren、Tsuei-Ju Wu、Xiaolan Shen、Kathryn A. Lyons、An-Hua Mao、Josephine R. Carlin、Bindhu V. Karanam、Stella H. Vincent、Kang Cheng、Mark T. Goulet

  DOI：10.1016/s0960-894x(01)00512-1

  日期：2001.10

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.