6-(4-hydroxymethylphenoxy)nicotinonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4-hydroxymethylphenoxy)nicotinonitrile
• 英文别名: 2-(4-hydroxymethyl-phenoxy)-isonicotinonitrile；2-[4-(Hydroxymethyl)phenoxy]-4-pyridinecarbonitrile；2-[4-(hydroxymethyl)phenoxy]pyridine-4-carbonitrile
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: CWZNODZTUAJQON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-hydroxymethylphenoxy)nicotinonitrile 在 咪唑 、 碘 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Discovery of dual positive allosteric modulators (PAMs) of the metabotropic glutamate 2 receptor and CysLT1 antagonists for treating migraine headache

  摘要：

  Pyridylmethylsulfonamide series were the first reported example of positive allosteric modulators (PAM) of the mGlu(2) receptor. The hydroxyacetophenone scaffold is a second series of mGlu(2) PAMs we have identified. This series of molecules are potent mGlu(2) potentiators and possess significant CysLT1 (cysteinyl leukotriene receptor 1) antagonist activity, showing in vivo efficacy in a dural plasma protein extravasation (PPE) model of migraine. In this paper, we describe the dual SAR, pharmacokinetics and preclinical in vivo efficacy data for a tetrazole containing hydroxyacetophenone scaffold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.049
• 作为产物：
  描述：

  2-氯-4-氰基吡啶 、 对羟基苯甲醇 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以32%的产率得到6-(4-hydroxymethylphenoxy)nicotinonitrile
  参考文献：
  名称：

  Discovery of dual positive allosteric modulators (PAMs) of the metabotropic glutamate 2 receptor and CysLT1 antagonists for treating migraine headache

  摘要：

  Pyridylmethylsulfonamide series were the first reported example of positive allosteric modulators (PAM) of the mGlu(2) receptor. The hydroxyacetophenone scaffold is a second series of mGlu(2) PAMs we have identified. This series of molecules are potent mGlu(2) potentiators and possess significant CysLT1 (cysteinyl leukotriene receptor 1) antagonist activity, showing in vivo efficacy in a dural plasma protein extravasation (PPE) model of migraine. In this paper, we describe the dual SAR, pharmacokinetics and preclinical in vivo efficacy data for a tetrazole containing hydroxyacetophenone scaffold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.049

文献信息

• Potentiators Of Glutamate Receptors
  申请人：Aicher Daniel Thomas

  公开号：US20080096930A1

  公开（公告）日：2008-04-24

  The present invention provides compounds of formula (I); pharmaceutical compositions thereof, and methods of using the same, processes or preparing the same, and intermediates thereof.

  本发明提供了式（I）的化合物；其制药组合物和使用方法，制备方法或中间体。
• VERFAHREN ZUR HERSTELLUNG VON LEDER
  申请人：BASF SE

  公开号：EP1592814B1

  公开（公告）日：2010-10-13
• VERFAHREN ZUR HERSTELLUNG VON LEDER UNTER VERWENDUNG VON POLYMERISATEN
  申请人：BASF Aktiengesellschaft

  公开号：EP1651781A1

  公开（公告）日：2006-05-03
• VERFAHREN ZUR HERSTELLUNG VON COPOLYMERISATEN
  申请人：BASF Aktiengesellschaft

  公开号：EP1668041B1

  公开（公告）日：2007-01-24
• WÄSSRIGE DISPERSIONEN VON COPOLYMERISATEN, IHRE HERSTELLUNG UND VERWENDUNG
  申请人：BASF SE

  公开号：EP1670859B1

  公开（公告）日：2010-03-17