3-acetoxy-N-acetyl-6-cyano-2,2-dimethyl-N-phenyl-2H-1-benzopyran-4-carboxamide | 135144-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-acetoxy-N-acetyl-6-cyano-2,2-dimethyl-N-phenyl-2H-1-benzopyran-4-carboxamide
• 英文别名: [4-[Acetyl(phenyl)carbamoyl]-6-cyano-2,2-dimethylchromen-3-yl] acetate
• CAS: 135144-43-3
• 化学式: C₂₃H₂₀N₂O₅
• 分子量: 404.422
• InChiKey: VRUQKLSEMRPKSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-cyano-2,2-dimethyl-2H-1-benzopyran-3-one 在 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.75h， 生成 3-acetoxy-N-acetyl-6-cyano-2,2-dimethyl-N-phenyl-2H-1-benzopyran-4-carboxamide
  参考文献：
  名称：

  Relaxant activity of 6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carboxamides and -thiocarboxamides and their analogs in guinea pig trachealis

  摘要：

  Structural modifications of the potassium channel activator cromakalim (1) are described in which the amide moiety at C-4 has been replaced by carboxamide and thiocarboxamide functions. Analogues in which the hydroxyl group at C-3 has been oxidized or removed are also disclosed. Such analogues display an interesting profile of smooth muscle relaxant activity in the guinea pig isolated trachea, not all of which appears to result from the opening of potassium channels, but few compounds retain useful in vivo activity. However, one compound in particular, 6-cyano-2,2-dimethyl-N-methyl-2H-1-benzopyran-4-thiocarboxamide (13) was shown to be a potent potassium channel activator in vitro and to provide prolonged protection to guinea pigs from the respiratory effects of inhaled histamine.

  DOI：

  10.1021/jm00112a037

文献信息

• Relaxant activity of 6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carboxamides and -thiocarboxamides and their analogs in guinea pig trachealis
  作者：Jonathan R. S. Arch、Derek R. Buckle、Claire Carey、Hilary Parr-Dobrzanski、Andrew Faller、Keith A. Foster、Catherine S. V. Houge-Frydrych、Ivan L. Pinto、David G. Smith、Stephen G. Taylor

  DOI：10.1021/jm00112a037

  日期：1991.8

  Structural modifications of the potassium channel activator cromakalim (1) are described in which the amide moiety at C-4 has been replaced by carboxamide and thiocarboxamide functions. Analogues in which the hydroxyl group at C-3 has been oxidized or removed are also disclosed. Such analogues display an interesting profile of smooth muscle relaxant activity in the guinea pig isolated trachea, not all of which appears to result from the opening of potassium channels, but few compounds retain useful in vivo activity. However, one compound in particular, 6-cyano-2,2-dimethyl-N-methyl-2H-1-benzopyran-4-thiocarboxamide (13) was shown to be a potent potassium channel activator in vitro and to provide prolonged protection to guinea pigs from the respiratory effects of inhaled histamine.