(3R,4S)-3-Amino-4-hydroxy-2,2-dimethyl-chroman-6-carbonitrile | 130867-14-0

• 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: (3R,4S)-3-Amino-4-hydroxy-2,2-dimethyl-chroman-6-carbonitrile
• 英文别名: (3R,4S)-3-amino-4-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
• CAS: 130867-14-0
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: ZNHHSBKGWNHWST-WDEREUQCSA-N

物化性质

• 沸点：
  364.8±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-Amino-4-hydroxy-2,2-dimethyl-chroman-6-carbonitrile 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到3-Amino-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile
  参考文献：
  名称：

  Synthesis and antihypertensive activity of 3-[(substituted-carbonyl)amino]-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity of a series of novel 3-[(subtituted-carbonyl)amino]-2H-1-benzopyran-4-ols, administered orally to spontaneously hypertensive rats, are described. Optimum activity in this series was observed for compounds with branched alkyl or branched alkylamino groups flanking the carbonyl or thiocarbonyl group (21, 31-33), which were approximately equipotent to cromakalim. Replacement of the 4-hydroxyl group by hydrogen, methoxy, or amino in this series only led to a slight reduction in potency. These observations are in marked contrast to the structure-activity relationships previously found for the 4-amidobenzopyran-3-ols. The antihypertensive activity of representative compounds 15 and 33 was attenuated by preatreatment with glibenclamide, and thus these compounds may belong to the series of drugs which have been classified as potassium channel activators.

  DOI：

  10.1021/jm00087a018
• 作为产物：
  描述：

  trans-6-cyano-2,2-dimethyl-3,4-dihydro-3-(t-butoxycarbonyl)amino-2H-1-benzopyran-4-ol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (3R,4S)-3-Amino-4-hydroxy-2,2-dimethyl-chroman-6-carbonitrile
  参考文献：
  名称：

  Synthesis and antihypertensive activity of 3-[(substituted-carbonyl)amino]-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity of a series of novel 3-[(subtituted-carbonyl)amino]-2H-1-benzopyran-4-ols, administered orally to spontaneously hypertensive rats, are described. Optimum activity in this series was observed for compounds with branched alkyl or branched alkylamino groups flanking the carbonyl or thiocarbonyl group (21, 31-33), which were approximately equipotent to cromakalim. Replacement of the 4-hydroxyl group by hydrogen, methoxy, or amino in this series only led to a slight reduction in potency. These observations are in marked contrast to the structure-activity relationships previously found for the 4-amidobenzopyran-3-ols. The antihypertensive activity of representative compounds 15 and 33 was attenuated by preatreatment with glibenclamide, and thus these compounds may belong to the series of drugs which have been classified as potassium channel activators.

  DOI：

  10.1021/jm00087a018

文献信息

• Benzopyran-type compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0375449B1

  公开（公告）日：1995-02-15