N,1-bis[(2-methoxyphenyl)methyl]-5-methyltriazole-4-carboxamide | 1093236-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,1-bis[(2-methoxyphenyl)methyl]-5-methyltriazole-4-carboxamide
• CAS: 1093236-99-7
• 化学式: C₂₀H₂₂N₄O₃
• 分子量: 366.42
• InChiKey: DPNLPCBMMONFIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,1-bis[(2-methoxyphenyl)methyl]-5-methyltriazole-4-carboxamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到N,1-bis[(2-hydroxyphenyl)methyl]-5-methyltriazole-4-carboxamide
  参考文献：
  名称：

  1,2,3-Triazol-carboxanilides and 1,2,3-triazol-(N-benzyl)-carboxamides as BK-potassium channel activators. XII

  摘要：

  The chemical structures of many synthetic activators of large-conductance calcium-activated potassium channels (BK channels) satisfy a simple pharmacophore model, consisting of two appropriately substituted phenyl rings connected by a linker of a heterogeneous nature. In this paper, a series of new compounds with modifications of the linker portion of the above pharmacophore are described. In particular, in these new derivatives, the linker portion is represented by a 1,2,3-triazole-carboxamide group, which can be viewed as a combination of two different kinds of linker, independently used in previous series of BK-openers: the amide function and the 1,2,3-triazole ring. The overall finding of this study indicated that the triazole-carboxamide derivatives were generally poorly effective and that this structural modification of the linker is deleterious for activity on BK channels. Therefore, it can be hypothesized that the increase of the steric hindrance of the linker and/or the increase of the distance between the two aromatic portions are negative for the interaction with the biological target. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.032
• 作为产物：
  描述：

  邻甲氧基苄胺 、 1-[(2-Methoxyphenyl)methyl]-5-methyltriazole-4-carbonyl chloride 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 N,1-bis[(2-methoxyphenyl)methyl]-5-methyltriazole-4-carboxamide
  参考文献：
  名称：

  1,2,3-Triazol-carboxanilides and 1,2,3-triazol-(N-benzyl)-carboxamides as BK-potassium channel activators. XII

  摘要：

  The chemical structures of many synthetic activators of large-conductance calcium-activated potassium channels (BK channels) satisfy a simple pharmacophore model, consisting of two appropriately substituted phenyl rings connected by a linker of a heterogeneous nature. In this paper, a series of new compounds with modifications of the linker portion of the above pharmacophore are described. In particular, in these new derivatives, the linker portion is represented by a 1,2,3-triazole-carboxamide group, which can be viewed as a combination of two different kinds of linker, independently used in previous series of BK-openers: the amide function and the 1,2,3-triazole ring. The overall finding of this study indicated that the triazole-carboxamide derivatives were generally poorly effective and that this structural modification of the linker is deleterious for activity on BK channels. Therefore, it can be hypothesized that the increase of the steric hindrance of the linker and/or the increase of the distance between the two aromatic portions are negative for the interaction with the biological target. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.032

文献信息

• 1,2,3-Triazol-carboxanilides and 1,2,3-triazol-(N-benzyl)-carboxamides as BK-potassium channel activators. XII
  作者：Vincenzo Calderone、Francesca Lidia Fiamingo、Gabriella Amato、Irene Giorgi、Oreste Livi、Alma Martelli、Enrica Martinotti

  DOI：10.1016/j.ejmech.2008.02.032

  日期：2008.11

  The chemical structures of many synthetic activators of large-conductance calcium-activated potassium channels (BK channels) satisfy a simple pharmacophore model, consisting of two appropriately substituted phenyl rings connected by a linker of a heterogeneous nature. In this paper, a series of new compounds with modifications of the linker portion of the above pharmacophore are described. In particular, in these new derivatives, the linker portion is represented by a 1,2,3-triazole-carboxamide group, which can be viewed as a combination of two different kinds of linker, independently used in previous series of BK-openers: the amide function and the 1,2,3-triazole ring. The overall finding of this study indicated that the triazole-carboxamide derivatives were generally poorly effective and that this structural modification of the linker is deleterious for activity on BK channels. Therefore, it can be hypothesized that the increase of the steric hindrance of the linker and/or the increase of the distance between the two aromatic portions are negative for the interaction with the biological target. (C) 2008 Elsevier Masson SAS. All rights reserved.