[1-ethyl-6-(methyloxy)-1H-imidazo[4,5-c]pyridin-2-yl]acetonitrile | 925213-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: [1-ethyl-6-(methyloxy)-1H-imidazo[4,5-c]pyridin-2-yl]acetonitrile
• 英文别名: 1H-Imidazo[4,5-c]pyridine-2-acetonitrile, 1-ethyl-6-methoxy-；2-(1-ethyl-6-methoxyimidazo[4,5-c]pyridin-2-yl)acetonitrile
• CAS: 925213-65-6
• 化学式: C₁₁H₁₂N₄O
• 分子量: 216.242
• InChiKey: OZCHZTHLZVDYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-ethyl-6-(methyloxy)-1H-imidazo[4,5-c]pyridin-2-yl]acetonitrile 在 盐酸 、 sodium nitrite 、 sodium hydroxide 、 羟胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以385 mg的产率得到4-{1-ethyl-6-methoxy-1H-imidazo[4,5-c]pyridin-2-yl}-1,2,5-oxadiazol-3-amine
  参考文献：
  名称：

  Discovery of Aminofurazan-azabenzimidazoles as Inhibitors of Rho-Kinase with High Kinase Selectivity and Antihypertensive Activity

  摘要：

  The discovery, proposed binding mode, and optimization of a novel class of Rho-kinase inhibitors are presented. Appropriate substitution on the 6-position of the azabenzimidazole core provided subnanomolar enzyme potency in vitro while dramatically improving selectivity over a panel of other kinases. Pharmacokinetic data was obtained for the most potent and selective examples and one (6n) has been shown to lower blood pressure in a rat model of hypertension.

  DOI：

  10.1021/jm060873p
• 作为产物：
  描述：

  2,4-二甲氧基-5-硝基吡啶 在 palladium on activated charcoal 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 [1-ethyl-6-(methyloxy)-1H-imidazo[4,5-c]pyridin-2-yl]acetonitrile
  参考文献：
  名称：

  Discovery of Aminofurazan-azabenzimidazoles as Inhibitors of Rho-Kinase with High Kinase Selectivity and Antihypertensive Activity

  摘要：

  The discovery, proposed binding mode, and optimization of a novel class of Rho-kinase inhibitors are presented. Appropriate substitution on the 6-position of the azabenzimidazole core provided subnanomolar enzyme potency in vitro while dramatically improving selectivity over a panel of other kinases. Pharmacokinetic data was obtained for the most potent and selective examples and one (6n) has been shown to lower blood pressure in a rat model of hypertension.

  DOI：

  10.1021/jm060873p

文献信息

• Discovery of Aminofurazan-azabenzimidazoles as Inhibitors of Rho-Kinase with High Kinase Selectivity and Antihypertensive Activity
  作者：Robert A. Stavenger、Haifeng Cui、Sarah E. Dowdell、Robert G. Franz、Dimitri E. Gaitanopoulos、Krista B. Goodman、Mark A. Hilfiker、Robert L. Ivy、Jack D. Leber、Joseph P. Marino,、Hye-Ja Oh、Andrew Q. Viet、Weiwei Xu、Guosen Ye、Daohua Zhang、Yongdong Zhao、Larry J. Jolivette、Martha S. Head、Simon F. Semus、Patricia A. Elkins、Robert B. Kirkpatrick、Edward Dul、Sanjay S. Khandekar、Tracey Yi、David K. Jung、Lois L. Wright、Gary K. Smith、David J. Behm、Christopher P. Doe、Ross Bentley、Zunxuan X. Chen、Erding Hu、Dennis Lee

  DOI：10.1021/jm060873p

  日期：2007.1.1

  The discovery, proposed binding mode, and optimization of a novel class of Rho-kinase inhibitors are presented. Appropriate substitution on the 6-position of the azabenzimidazole core provided subnanomolar enzyme potency in vitro while dramatically improving selectivity over a panel of other kinases. Pharmacokinetic data was obtained for the most potent and selective examples and one (6n) has been shown to lower blood pressure in a rat model of hypertension.