methyl 6-cyano-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-4-carbodithioate | 135144-38-6

• 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: methyl 6-cyano-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-4-carbodithioate
• 英文别名: 6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-dithiocarboxylic acid methyl ester；Methyl 6-cyano-3-hydroxy-2,2-dimethylchromene-4-carbodithioate
• CAS: 135144-38-6
• 化学式: C₁₄H₁₃NO₂S₂
• 分子量: 291.395
• InChiKey: ISLJVJVYJPCACQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-cyano-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-4-carbodithioate 、 N-甲基苯胺 反应 12.0h， 以61%的产率得到6-cyano-2,2-dimethyl-3-hydroxy-N-methyl-N-phenyl-2H-1-benzopyran-4-thiocarboxamide
  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modifications of the potassium channel activator cromakalim (1) are described in which the amide moiety at C-4 has been replaced by carboxamide and thiocarboxamide functions.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
• 作为产物：
  描述：

  6-cyano-2,2-dimethyl-2H-1-benzopyran-3-one 、 碘甲烷 在 二硫化碳 作用下， 以 ice-water 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-cyano-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-4-carbodithioate
  参考文献：
  名称：

  Benzopyran derivatives

  摘要：

  以公式（I）表示的苯并吡喃衍生物：其中X表示=O，=S，=N-Z（Z表示低碳基团等），或=CHNO.sub.2；Y表示取代氨基团，烷氧基团，烷硫基团等，而R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6和R.sub.7分别表示氢原子，低碳基团等。这些苯并吡喃衍生物表现出K.sup.+通道激活活性，并广泛应用于抗哮喘药、抗癫痫药等。

  公开号：

  US05412117A1

文献信息

• NOVEL BENZOPYRAN DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0541807A1

  公开（公告）日：1993-05-19

  A benzopyran derivative represented by general formula (I), which has a K⁺ channel activating effect and so is widely applicable for treating, for example, asthma and epilepsy, wherein X represents =O, =S, =N-Z (wherein Z represents lower alkyl, etc.), or = CHNO₂; Y represents substituted amino, alkoxy, alkylthio, etc.; and R₁ to R₇ represent each hydrogen, lower alkyl, etc.

  通式(I)代表的苯并吡喃衍生物，具有激活K⁺通道的作用，因此广泛用于治疗哮喘和癫痫等，其中X代表＝O、＝S、＝N-Z（其中Z代表低级烷基等）或＝CHNO₂；Y代表取代的氨基、烷氧基、烷硫基等；R₁至R₇各自代表氢、低级烷基等。
• US5412117A
  申请人：——

  公开号：US5412117A

  公开（公告）日：1995-05-02