6-(4-hydroxyphenoxy)nicotinonitrile | 639091-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-hydroxyphenoxy)nicotinonitrile
• 英文别名: 6-(4-Hydroxyphenoxy)pyridine-3-carbonitrile
• CAS: 639091-31-9
• 化学式: C₁₂H₈N₂O₂
• mdl: MFCD12800336
• 分子量: 212.208
• InChiKey: UQGMXCBCLPEMKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  406.4±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-hydroxyphenoxy)nicotinonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到6-(4-hydroxyphenoxy)nicotinic acid
  参考文献：
  名称：

  Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

  摘要：

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.052
• 作为产物：
  描述：

  6-[(4-benzyloxy)phenoxy]nicotinonitrile 在 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 生成 6-(4-hydroxyphenoxy)nicotinonitrile
  参考文献：
  名称：

  苯氧基吡啶衍生物作为钠钙交换剂的新型抑制剂的合成及其构效关系。

  摘要：

  钠钙交换剂（NCX）被称为控制心肌细胞中Ca（2+）浓度的转运蛋白。在心力衰竭和心肌缺血-再灌注的情况下，NCX是导致心律失常的瞬态内向电流的基础，该电流导致心动过速后的去极化和非折返性延迟。NCX是治疗心力衰竭和心肌缺血-再灌注的有吸引力的靶标。我们基于化合物3设计并合成了一系列苯氧基吡啶衍生物。已评估了这些衍生物对CCL39细胞中NCX反向和正向模式的抑制活性。我们发现了几种新型的有效NCX抑制剂（39q，48k），它们对反向NCX抑制活性具有很高的选择性。

  DOI：

  10.1016/j.bmc.2004.07.038

文献信息

• Synthesis and structure–activity relationships of phenoxypyridine derivatives as novel inhibitors of the sodium–calcium exchanger
  作者：Takahiro Kuramochi、Akio Kakefuda、Hiroyoshi Yamada、Ippei Sato、Taku Taguchi、Shuichi Sakamoto

  DOI：10.1016/j.bmc.2004.07.038

  日期：2004.10

  nonreentrant initiation of ventricular tachycardia. NCX is an attractive target for treatment in heart failure and myocardial ischemia-reperfusion. We have designed and synthesized a series of phenoxypyridine derivatives, based on compound 3. These derivatives have been evaluated for their inhibitory activity against both the reverse and forward mode of NCX in CCL39 cells. We have discovered several

  钠钙交换剂（NCX）被称为控制心肌细胞中Ca（2+）浓度的转运蛋白。在心力衰竭和心肌缺血-再灌注的情况下，NCX是导致心律失常的瞬态内向电流的基础，该电流导致心动过速后的去极化和非折返性延迟。NCX是治疗心力衰竭和心肌缺血-再灌注的有吸引力的靶标。我们基于化合物3设计并合成了一系列苯氧基吡啶衍生物。已评估了这些衍生物对CCL39细胞中NCX反向和正向模式的抑制活性。我们发现了几种新型的有效NCX抑制剂（39q，48k），它们对反向NCX抑制活性具有很高的选择性。
• Design, synthesis and insecticidal evaluation of aryloxy dihalopropene derivatives
  作者：Ji-Chun Yang、Miao Li、Qiao Wu、Chang-Ling Liu、Xiu-Hui Chang

  DOI：10.1016/j.bmc.2015.09.030

  日期：2016.2

  Plutella xylostella (P. xylostella) is a highly migratory, cosmopolitan species and one of the most important pest of cruciferous crops worldwide. Pyridalyl as a novel class of insecticides has good efficacy against P. xylostella. On the basis of the commercial insecticide pyridalyl, a series of new aryloxy dihalopropene derivatives were designed and synthesized by using Intermediate Derivatization Methods. Their chemical structures were confirmed by H-1 NMR, high-resolution mass spectrum (HRMS), and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds against P. xylostella were evaluated. The results of bioassays indicated that most of the compounds showed moderate to high activities at the tested concentration, especially compounds 10e and 10g displayed more than 75% insecticidal activity against P. xylostella at 6.25 mg/L, while pyridalyl showed 50% insecticidal activity at the same concentration. The field trials result of the insecticidal activities showed that compound 10e as a 10% emulsifiable concentrate (EC) was effective in the control of P. xylostella at 75-150 g a. i./ha, and the mortality of P. xylostella for treatment with compound 10e at 75 g a. i./ha was equivalent to pyridalyl at 105 g a.i./ha. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor
  作者：Takahiro Kuramochi、Akio Kakefuda、Hiroyoshi Yamada、Issei Tsukamoto、Taku Taguchi、Shuichi Sakamoto

  DOI：10.1016/j.bmc.2005.03.052

  日期：2005.6

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.