4-(pyridin-2-ylmethoxy)toluene | 16173-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(pyridin-2-ylmethoxy)toluene
• 英文别名: 2-((p-tolyloxy)methyl)pyridine；2-[(4-Methylphenoxy)methyl]pyridine
• CAS: 16173-82-3
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: FIKPOAQRJVKWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(pyridin-2-ylmethoxy)toluene 在 四(三苯基膦)钯 、 MMPP 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 1-Methyl-2-[(4-methylphenoxy)methyl]-4-[(4-methylphenyl)methyl]pyridin-1-ium;trifluoromethanesulfonate
  参考文献：
  名称：

  Strategies To Reduce hERG K⁺Channel Blockade. Exploring Heteroaromaticity and Rigidity in Novel Pyridine Analogues of Dofetilide

  摘要：

  Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG interaction but most importantly may reveal drug design principles to reduce hERG affinity. In the present study, a novel library of neutral and positively charged heteroaromatic derivatives of the class III antiarrhythmic agent dofetilide was synthesized and assessed for hERG affinity in radioligand binding and manual patch clamp assays. Structural modifications of the pyridine moiety, side chain, and peripheral aromatic moieties were evaluated, thereby revealing approaches for reducing hERG binding affinity. In particular, we found that the extra rigidity imposed close to the positively charged pyridine moiety can be very efficient in decreasing hERG affinity.

  DOI：

  10.1021/jm301564f
• 作为产物：
  描述：

  对甲酚 、 2-(溴甲基)吡啶氢溴酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以72%的产率得到4-(pyridin-2-ylmethoxy)toluene
  参考文献：
  名称：

  Strategies To Reduce hERG K⁺Channel Blockade. Exploring Heteroaromaticity and Rigidity in Novel Pyridine Analogues of Dofetilide

  摘要：

  Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG interaction but most importantly may reveal drug design principles to reduce hERG affinity. In the present study, a novel library of neutral and positively charged heteroaromatic derivatives of the class III antiarrhythmic agent dofetilide was synthesized and assessed for hERG affinity in radioligand binding and manual patch clamp assays. Structural modifications of the pyridine moiety, side chain, and peripheral aromatic moieties were evaluated, thereby revealing approaches for reducing hERG binding affinity. In particular, we found that the extra rigidity imposed close to the positively charged pyridine moiety can be very efficient in decreasing hERG affinity.

  DOI：

  10.1021/jm301564f

文献信息

• [EN] HETEROARYL COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLES ET LEURS UTILISATIONS
  申请人：AVILA THERAPEUTICS INC

  公开号：WO2009051822A1

  公开（公告）日：2009-04-23

  The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

  本发明提供了化合物、药学上可接受的组合物以及使用它们的方法。
• 2-Pyridylmethyl ether: a readily removable and efficient directing group for amino acidligand accelerated ortho-C–H olefination of phenols
  作者：Xuefeng Cong、Jingsong You、Ge Gao、Jingbo Lan

  DOI：10.1039/c2cc37291f

  日期：——

  2-Pyridylmethyl ether-directed ortho-C-H olefination of phenols via a seven-membered cyclopalladated intermediate has been disclosed to construct a variety of ortho-alkenyl phenols and ortho-alkyl phenols.

  已经公开了经由七元环palpalated的中间体的苯酚的2-吡啶基甲基醚指导的邻-CH烯化反应以构建多种邻链烯基酚和邻烷基酚。
• PYRIMIDINE DERIVATIVES
  申请人：Kettle Jason Grant

  公开号：US20110046108A1

  公开（公告）日：2011-02-24

  The invention concerns benzamide compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R 1 , ring A, n, R 3 , and R 4 are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions which are sensitive to the inhibition of EphB4, and/or EphA2 and/or Src kinases.

  这项发明涉及Formula (I)的苯甲酰胺化合物或其药用可接受的盐，其中R1、环A、n、R3和R4如描述中所定义。本发明还涉及制备这种化合物的方法、含有它们的药物组合物以及它们在制造用作抗增殖剂的药物中的用途，用于预防或治疗对EphB4、EphA2和/或Src激酶抑制敏感的肿瘤或其他增殖病症。
• [EN] HETEROARYL COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLE ET UTILISATIONS ASSOCIÉES
  申请人：AVILA THERAPEUTICS INC

  公开号：WO2011090760A1

  公开（公告）日：2011-07-28

  The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

  本发明提供了化合物，其药物学上可接受的组成物以及使用它们的方法。
• NOVEL PYRIDINONE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2-RECEPTORS
  申请人：Imogai Julien Hassan

  公开号：US20070213323A1

  公开（公告）日：2007-09-13

  The present invention relates to novel compounds, in particular novel pyridinone derivatives according to Formula (I) X R1 N Y (I) R2 R3 wherein all radicals are defined in the application. The compounds according to the invention are positive allosteric modulators of metabotropic receptors-subtype 2 (“mGluR2”) which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及新型化合物，特别是按照公式（I）X R1 N Y（I）R2 R3定义的新型吡啶酮衍生物。该发明的化合物是代谢型受体亚型2（“mGluR2”）的正向变构调节剂，适用于治疗或预防与谷氨酸功能障碍相关的神经系统和精神障碍以及涉及代谢型受体亚型2的疾病。特别是，这些疾病是选择自焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统疾病的一组。本发明还涉及制备这种化合物和组合物的制药组合物和制备过程，以及利用这种化合物预防和治疗涉及mGluR2的这些疾病的用途。